We replaced our sales team with 20 AI agents—here’s what happened next | Jason

Jason LemkinHere's the mistake that 99% of founders and sales reps make. We're not really selling in B2B, we're solving problems. Our job as sales reps in SaaS is to not sell a used car, okay? We are selling a Tesla Model 3 performance. It has competition, I might not need it this week, but it's pretty darn good. Let me help you get you into that Model 3 performance today. I've even got a special discount for the end of this month, and let me just help you. I've spent four calls answering all your questions and I've explained to you all the things and why the supercharging network is better than the regular one that doesn't really work at the charger near your house. I've gone on Google and I've seen there's no charging network near your house. There's only Superchargers. I got you, don't I? That's the job of SaaS and sales because we're not selling commodities.

LennyToday, my guest is Jason Lemkin. Jason created and runs Saastr, the world's largest community for SaaS and B2B founders. He also runs two of the biggest town conferences every year, one in the Bay Area, which attracts over 15,000 people, and one in Europe with over 3,000 SaaS executives, founders, and entrepreneurs. Before Saastr, Jason was the CEO and co-founder of EchoSign, which he grew to over 100 million ARR and then sold to Adobe where he ended up as a vice president of their web services business. If you follow Jason on Twitter or LinkedIn, you know how much wisdom he has to share about all aspects of building a successful SaaS business.

In our conversation, we focus on what I find most product leaders have the least experience in, building a sales team. We get very practical and tactical on how long you should wait to hire your first salesperson, what your one to two first hire should look like, why you should actually hire two salespeople, not just one initially, how to comp them, how to interview them, when it's time to hire a VP of sales, how to avoid your salespeople flaming out and burning through all your cash. We also get into how to make the product and sales relationship healthier, including how to push back on sales and feature requests, why your head of product should be super involved in your sales process, how long you should make your trials, why you should avoid annual contracts, and so much more.
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Jason LemkinHey, I'm so excited. Long time. What's the expression? Long time fan, first time dialer or something?

LennyCaller?

Jason LemkinFirst time caller, yeah, first time caller.

LennyFirst time guest.

Jason LemkinI don't know if that exists in 2024 or not, but yeah, that's me. So thank you so much for letting me come.

LennyIt's absolutely my pleasure. I feel like you're the kind of guy that I knew would be on this podcast eventually, and I'm glad that we're finally doing this. I also feel like we can go in so many directions. I feel like you have so many insights on so many parts of building a business, especially a B2B business, but I thought it would be most interesting to dive deep into building your sales team, essentially trying to help people figure out how to start their sales team, scale their sales team, and all the elements they go into it. How does that sound?

Jason LemkinI think it's great. I think it's an evergreen topic, but I think there's remains a consistent set of confusion, fears around how to build a sales team, and it's evergreen. The tools change and the pace has changed, but the issues, I love to dig into them because we keep making the same mistakes as founders and executives again and again and again.

Lenny100% agree. It's such a black box to me. Sales, I've never done sales, and I'm always just like, "I have no idea what's going on here." So this is how I learned from folks like you. You touched on this now. Now, I wasn't going to get on this, but I think it'd be interesting just this question of, does everyone need a sales team? Will you need a sales team if you're listening as a founder? Is it simply, if you're a B2B business, you'll need a sales team? How should people think about, "Will I need a sales team?"

Jason LemkinIf you truly build a self-serve product, you can either never have a sales team or Slack defer it or Canva really defer it. Canva didn't really build a sales team until they were well north of 500 million in revenue because it's epic self-serve. Slack started all self-serve, and by the time they went public, the majority of their revenue was enterprise sales. So you can sequence things. You can have hybrid models like a third of Asana's revenue is still from self-serve, and two-thirds are from a self-serve motion. So there's all different hybrid things.

The most important thing though I've found is however you get those first 10, 15, 20 customers, be honest, be honest, and if you've talked to them as a founder and you know that they need a sales type motion, they need effort to deploy it, they have questions about security, they have questions about competition, they have onboarding requirements, and you say, "Hey, I don't like sales, so I'm going to do a PLG motion," you'll fail.
One of the things that I've done with so many founders over the years, and it shocks them at first, is your first 10, 15, 50 unaffiliated customers, the ones that find you from the ether, they're the next 50, 100, 200, 1,000, and you can either embrace them or run for them. Too many producty founders find that, "Hey, gosh, I'm going to have to do sales," and they exit it. They exit it.
I'll tell you a company I invested in 18 months ago when things were easier, maybe 20 months ago, they were doing 5 million in revenue, growing over 100% with the sales like motion. Things got harder, things got harder as they did for many of us, and they decided to fire the whole sales team, and now they're doing less than one from 5 million with beloved customers. If I told you the logos, your jaw would drop. Over 5,000 20 months ago to 1 million today because they fired the sales team because the founders didn't like sales, they thought it was icky, they didn't want to do it, they were tired of doing it. I can tell you several stories like this.
So you've got to be honest about the ... Sometimes we get it just right on day zero. Sometimes we know exactly how our company is going to work or Lenny's podcast is going to work. We can predict the future perfectly, but I find in B2B, a lot of times the industry, we end up winning. The segment of the industry, the type of customer is not what we initially thought and either lean into it and be a success or run from it because sales is icky and risk failure.

LennyWhen you talk about being honest, what you need to be honest about is that you need sales help to close customers?

Jason LemkinBe honest about that. Just be honest about, yes, the motion that it will take to get those first 10, 15, 20 customers, and if they were able to find you by putting their credit card and no one had to talk to them, then that's your DNA today. It doesn't mean you won't go up market later like a Slack or a Canva, but if you can get them all to do that and you never have to talk to them, then get really good at viral loops, get really good at almost B2C type motions, get really good at this kind of stuff and hire growth hackers and do the whole almost B2C-ish motion, which we have at self-serve, but if your first 10 customers come in and say, "You know what, Lenny, I'll pay you $5,000, but you've got to solve this problem I have with online video," that is not a self-serve motion. It is not a self-serve motion.

Even worse, sometimes worse is your first 10 customers, five of them sign up online, but it takes a huge amount of effort for 19 bucks a month, and then five say they'll pay you $5,000 a month. Some founders are like, "I'm going to work on the five that pay us 20 bucks a month, not the five that'll pay us $5,000 a year." I find too many folks that don't like sales, too many folks that have not had any life experience in a sales-led environment flee from those customers, and I've never seen that lead to success. We're surprised who our niche is sometimes. We talk about nailing our niche, but sometimes we're surprised that niche that finds us.

LennyThere's a lot of startups I've invested in that start off product-led growth and quickly realized, "This just isn't working," and many of them move to, "We need to actually hire salespeople and start to go top down."

Jason LemkinMost companies are a hybrid. Even there's weird hybrids like there's folks like Mongo and Snowflake. Mongo has, well, maybe Mongo's much better example, Mongo has a free low end version, and there's open source too. It's a little confusing, and then there's not a lot in the middle, and then there's a lot of big. There's all different ways to combine a product-led or self-serve motion with sales-led. Too many founders in the beginning think it's either or. It's not either or.

LennySo I think the big takeaway here is sales is not a question of if you're going to need a sales team, it's a matter of when. The Canva example is crazy. Maybe that's the

Jason LemkinBut they still have one. But they still have one now.

LennyThey still have one. I think Notion, I think at 10 million ARRs when they hired their first salesperson.

Jason LemkinThat makes sense.

LennySo I think the question that leads to is, what is a sign that you should start to hire your first salesperson?

Jason LemkinEven if you hate sales, even if you think it's icky, even if you don't like it, as a founder you've, 95 times out of 100, you've got to find a way at least to close the first 10 customers yourself. You've got to find a way. We could dig into how to do that if you don't like sales. The hack though is that even if you don't like sales, customers love to talk to the CEO. The customers love it. Here's the other thing, as a founder, you're really good at the product in the market, hopefully even in the early days. So what's important is even if you don't know how to do outbound, even if you don't know how to send a cold email, even if you don't how to do any of this stuff, and even if you don't know how to ask for a check, even if you don't know how to open or close, almost all founders are A+ middlers, A+ middlers, A+ middlers. Before we started, you and I talked about podcasts and content, and immediately it was an A+ conversation. Maybe you don't know how to close a big sponsor, I'm just making that up, and maybe you don't know how to find one, but once you have someone in your spider web, letting the conversation, you and I just had was A+, and any founder should be there by day one, by day one, and prospects love it.

If I want to buy CRM, I don't get to talk to Yamini at HubSpot or Marc Benioff, but I get to talk to you and your CRM company. It's magical for early adopters. So bear in mind, no matter how bad you think you are as a founder, you're pretty good at the middle part of sales. So find a way to get any prospects, get really good at the middle, and then work up your courage. Work up your courage, and find how to ask for next steps and money. What would it take, Lenny? How can we get going on Riverside? What would it take? We would love to have you. What would it take to get you going next week? You've got to learn that little motion, but you don't have to learn all the stuff you think is smarmy other than how to go from middle to just ask for how we can get going.

LennyI like this term, middlers. So just to make sure I understand what that means, in the middle of the conversation, you're not great at initiating, you're not great at closing, but you could talk about it.

Jason LemkinYeah, and this is where sales reps are terrible. Most sales reps, once you go beyond the five basic questions, they can't tell you how a database works or how to eliminate hallucinations from your product or how to do payroll in Eastern Southern Guam. The sales rep, and we can talk about this, they need help. They need help from the founders in the early days. They need help from sales engineers or product people, which is my favorite place to get the help as you scale, but they need help.

The beauty to founders is they don't need help in the middle. You can be 10 times better in the middle than any sales rep at your bigger competitor. If you're running, I am just making up CRM, but if you're running a new CRM startup, you can run circles around 98% of the sales reps at Salesforce or HubSpot. They have the brand, they have the partners, they have the integrations, but they cannot answer the questions you can answer.

LennyOkay. So you close the first 10 customers. What are other signs that, "Okay. Now is really the time we need to start hiring sales"?

Jason LemkinI think as soon as you've got those 10 customers and more than 20% of your time is booked up with customers, you need leverage. You need leverage. You've got to get ... If you do it too early, if you're not spending 20% of your time in sales and 20% of your time in recruiting, you're failing as a founder. You need 20% of each, 20% in sales and 20% recruiting. Nothing else really matters at some level as a CEO, maybe not as founders, but as CEOs. Once you cross the 20%, you need leverage or your calendar will die. So you need to hire one rep and you've got to hire two because otherwise, there's no A-B test. You have to A-B test humans. You have to A-B test humans. You've got to hire two as hard as it is, and there's just one cheat code to those first two. There's one cheat code.

I talked to so many founders that screwed up their first sales hires, and they always nod when they hear it. Those first couple reps have to be people you would buy your own product from. That's it. Now we can talk about other criteria. We can talk about normalizing for deal size. We can talk about industry expertise. We can talk about all this kind of stuff, but when you go out as a first time founder and interview 30 reps, and you're going to have to interview 30, and 20 are just going to break your brain because they don't do any work and they don't do any prep and they didn't even go to your website. Then eight of the next 10 are okay, but you know it's not really going to work, but you might hire them if you get tired.
If you're lucky, one or two of them, they're like magicians. They ask the right questions, which we could talk about. Then take a pause and say, "Look, no matter how strange their background was, whatever they did, it's not the right background. It's not our same deal size. It's not our industry. They actually weren't very good at their last job. They got let go at their last job, but I would buy from Lenny. I know. I've been doing this for a year. Every day, I would buy from Lenny because Lenny just explained to me my product and my customer's problems in a way that I actually believe. Forget about what's on her LinkedIn or his LinkedIn. I would buy from Lenny."
That rep always works because you can trust them with those leads. Almost every first time founder hires someone because they worked at Twilio or CloudFlare or wherever, and they talk the talk and they can say ACV and NRR, and they can talk all these acronyms. None of which matter. None of which matter. We all get attracted to logos on our resume, but in our gut, I always ask them, "Did you know that Jason was going to ... Would you buy from Jason?" They're like, "You're right. I wouldn't have bought from Jason, but he worked at Twilio." So just wait, wait and interview 30 sales reps, however you find them through LinkedIn, through use recruiters, use contingent recruiters. It's exhausting. Do everything. Work your network and then be flexible in the beginning. We're looking for pirates and romantics in the early days. We are not looking for folks with massive sales operations teams and enablement teams. You're looking for that quirky one that's got a few extra IQ points, that for reasons that make no sense has fallen in love with your little product that is so feature poor and does nothing, but they love it, they love it, they love it.
My first rep I had this back in the day, he had gotten let go by a prior startup and he was struggling and he was living in his brother's garage at the time. This was not your number one person at Snowflake, but of all the 30, he came in and what's now Adobe sign? EchoSign. He described the whole problem. He described how we would solve the problem for our customers in the early days of this category. It was clear, whatever it took we needed him and whatever we needed to backfill the garage or whatever, this was the only one that could sell the product, and he did it for a decade. Closed our first five-figure deal, first six-figure deal, first seven-figure TCV deal. Didn't scale completely. Inside of Adobe was harder to scale inside of a 20,000 person company than it was in a six-person company, but he was still there. He still made that far to the journey, but he was the only one that I knew that I would buy my product from, not that I would buy something from, but I would buy my product from.
Leads are so precious in the early days. It's so hard to find leads. That's the problem. You hire this perfect person from Snowflake and you have three leads a month and you give him two and he doesn't close them, your company's going to die. Leads are so precious. That's what folks don't get. So wait, and I know it's painful, and I know most founders have hired this person with the right LinkedIn that they wouldn't buy their product from. Just keep interviewing. You need that quirky pyromaniac that loves your product and can sell it. They're out there.

LennyAmazing advice. Wow. There's so much there. I'm going to follow a couple threads there. In terms of the level, I know a lot of people make the mistake of going with a VP of sales pretty quickly. What's your advice? I know you talked about general attributes, but what's your advice for the level and seniority of these first two hires?

Jason LemkinTwo things, one that's evergreen and one that's maybe especially apropos for today's environment. The evergreen one, which I've talked about for over a decade, and I think folks that have been through it will see it, which is you need two sales reps hitting quota closing deals before you're ready to hire a manager for them. Almost all VPs of sales, their job is to take you from rep three to 300, to take you from three to 300, to take something that's just starting to repeat, a script that's just starting to work, leads that are just starting to come in. Then take Lenny and Jason, the two reps I have, as quirky as they are, they're crushing it.

Then I'm going to hire a more heterogeneous type of person going forward. I'm going to hire the person from Cloudfare. They can't all be like Lenny and Jason, they're pretty quirky, but at least I can learn from them. What's working? What are the objections? How do we get around that feature gap? We're one year old, we're two years old. We've got a lot of feature gaps. This integration doesn't quite work. How do we box around those issues? How do we sell our 10x feature? Because if you're a startup, your product isn't very good, your software is not very good, and you have a competitor, but you have some 10x feature that is driving people to buy you something you're doing that does not exist in the marketplace.
The really good reps get insanely good at selling that, and the folks off the street, the new VPs often doesn't even understand the 10x feature. It's too subtle. It's too subtle. Why? The fact that your product is localized in Portuguese magically means you can win these deals. I'm making up something that doesn't quite make sense. So you need two reps that are hitting quota and then you hire VP of sales. If you hire it before then, you're doing a Hail Mary. It ain't going to work. It never, ever, never, ever, ever, never, ever works. You're asking them to find product market fit to be the first rep, to be the second rep and scale it all at the same time. It's mission impossible to do all four at the same time.
So that's the biggest mistake is, Lenny, I can't get sales going at my company. I can't do it, but I raised $4 million in my C+ round. I'm going to go out and hire the VP of sales. That VP of sales will not be there in eight months. You know what else? 2 million of the four will be gone because they'll never understand the product. They will never understand. There's so many things we could talk about, but if there's one thing I could reinforce for this audience, it's that early sales team, they've got to be product gurus for your product audience. They've got to be product experts. Later as you scale, they can't be or you can't scale.
When I started, when I came out of my own startup and started interviewing other folks, I remember I would interview a lot of folks at places like GitHub back in the day. I'd be like, "Do you have a technical background? Are you an engineer? Have you ever built any software?" They're like, "No, I don't. I don't know. I don't know," and I was like, "I was curious how you could do it," but GitHub was so well-established that it's 10 questions. It's 10 questions and grab a sales engineer. It's 10 questions and grab ... So you got to be really good at 10 and then you grab a sales engineer. That doesn't work in the early estate startups. So you've got to find these sales folks that are a bit of product savants and dropping the VP of sales in that isn't a product savant, which is a big issue. That's all mister or miss process. This is the issue. They're all mister or miss process.
So the second point I wanted to make, and I was on the fence for years of when you hire a VP of sales, do they need to carry a bag? Do they need to sell themselves or not? Does it matter? Does it matter? I wasn't sure for a long time. The reason I wasn't sure for a long time, it's not that you don't want a VP of sales carrying a bag. I do think a VP of engineering also should commit code. We can talk about that.

LennyCarrying a bag, meaning close sales themselves?

Jason LemkinYeah, not just be a boss.

LennyHave a quota.

Jason LemkinYeah, have a quote. The reason I was on the fence was because I was like, "Well, listen, in theory it's great, but let's say you're a hot startup and you want to go from two to six this year." So I want to add 4 million in new bookings, and let's say I can do 400K in quota per rep. That means I got to have 10 reps. She walks in with two. I'm at a race, aren't I? I got to hire eight in the next six months to hit my plan, and I got to put numbers on the board. If I'm going to out there as an individual contributor sales rep, I'm never going to hire eight people, am I? It's never going to happen.

So I used to say I don't know if it matters, but what I've learned the last 18 to 20 months when everyone has gotten lazy, Lenny, everyone in tech has gotten lazy, is I see way too many VPs of sales that come in and never have any idea how to sell the product, never, never. They only want to be managers.
Now, whether they carry a bag or whether what they do is they join calls with the reps, whether they backfill the reps, you want your VP of sales in deals 20, 30 hours a week when they start. I see VPs of sales today start, they're in no deals. I'll go to a board meeting and a VP of sales will be there two, three months, and they'll have a look on the board. I'm like, "How's it going with Airbnb?" and they'll be like, "I don't know. I got to ask John." Doesn't know because it isn't in the deal, isn't even in the deal. So I see this too often.
Another company I'm on the board on, I really like this VP of sales a lot. He joined and six months in, sales were down from where, the new bookings were down from where they were six months before. He was honest. He's like, "The biggest problem is I feel like I didn't have time to learn this product. It's a complicated product. It's more complicated than the product I last sold, and I just didn't have time."

LennyJason, this conversation is going exactly how I'd hoped. There's so much actionable advice here. Let me try to summarize a little bit of the things you've said and then keep going. So let me know what I'm missing here. I'm going to try to just highlight some of the important things you mentioned. So in terms of when it makes sense to start hiring your first salesperson, a couple of things you shared is you've closed the first 10 customers on your own as founders. If you're spending more than 20% of your time on sales and you need to start creating more leverage. I'll throw in one other thing I've heard and just to tell me if this is also true, that there's a repeatable process you've created. You can sell consistently enough or you can tell someone, "Here's how I've been selling." Is that right?

Jason LemkinYeah. If you hire a VP of sales before then, it's approaching 100% chance of failure.

LennyI see. So you can hire the first two reps before you're like, "Here's a pretty good process that has worked for me a number of times."

Jason LemkinYeah. Listen, as hard as it is for a lot of founders to even get their arms around, the reason is you've got to be that crummy first head of sales with them. You've got to manage those reps. You've got to be in the field with them. You've got to be figuring it out before you can hire the person. You just have to even if you're terrible at it because you're still going to be a good middler. You're still going to be a good middler.

LennyOkay. A few more things that stood out to me. One is hire two sales reps immediately, not just one. These reps you need to interview about 30 people. Eight will be pretty good, 20 will be terrible, and two, these are people that you can see selling your product and you would buy from them. They're often very quirky and not maybe a traditional sales background. They've never been VPs of sales, essentially. They're more like AEs and things like that historically or maybe not even salespeople historically. Is that right?

Jason LemkinI think you will regret it if you don't hire these first couple of sales reps that have a couple years of experience if you're in B2B with B2B sales. They need a couple of years of experience and they need a certain amount of maturity, and maturity is a real issue, and these are in any early hire because we just don't have time to babysit people. There's no onboarding, there's no training. So they need a couple years of experience, ideally something close to your deal size, we could chat about why, that would be nice, and enough maturity that you can trust them with that lead. You can trust them with your customer.

LennyOkay. Then you hire a VP of sales once you're ready to go from three to 300 reps. Your advice is also give the VP of sales a bag slash a quota slash they need to be doing sales themselves in today's world.

Jason LemkinAt least for a little while. More importantly, if they don't want to, I think in today's world you got to run from them. Exactly whether they fully carry a quota, a half quota, whether they backfill the sales team, you want a salesperson. Here's the thing, Lenny, you want a ... This is going to sound silly, but it's not. Trust me on this. For anyone watching, listening, you want a head of sales that actually wants to do sales. I got to tell you, and I'm still struggling with this myself after the last three years or so, so many folks in all functions, we could talk about other functions too, but especially in sales, don't want to do sales anymore. They don't want to do it. They don't want do it.

2021 was crazy because everything was too crazy. There's too much money, too much going on. 2022 was the knife falling. That was crazy too. 2023 was just hard. Whether it's burnout or whatever out or just too much change, I would say I've probably interviewed for different reasons, 50 VPs of sales in the last 12 months, I would say the majority don't want to do sales. It's my first screening question. That's why they got to carry a bag because it proves they actually still care about the craft.
The best sales folks love sales. It's a craft. They love money. Yes, they love money, and that does matter. Do not hire a sales rep that doesn't like money. Trust me on this one. There's 0% chance they'll work out either, but they also like the craft. They like honing the script. They like beating the competition. They like figuring out the counterfeit. They like figuring out the weapon and the 10x feature. They like working on a team. They like hunting. They love it, but then sometimes I just think burnout is always a reality, but I just think that the last three years have been so yo-yoed, that folks are just, they're out. They're out. Don't hire them no matter how smart they are, and that's the test.
I'll tell you, I talked with a really great VP of sales candidate that had worked with a top 10 tech company and I asked him what he wanted to do in this next role. He's like, "I've got a great team. I've got eight people that I can bring with me. We're ready to lock and load." I'm like, "Okay. Well, let me tell you one of my views in today's world is that you've got to actually visit more customers now, not less. In a distributed world, it's more important to visit customers." He lived in the East Bay in Pleasanton in the East Bay, which is maybe 20 minutes east of Oakland. He said, "I'm willing to visit customers, but I won't go as far as the peninsula in San Francisco." He's just happy at home. He's happy at home, Lenny, and he don't want to sell.
This guy has the best LinkedIn and the best references, but he don't want to sell anymore. He needs a job. He wants to be a VP of sales. I see this across the industry and I'm struggling to find answers. I think the biggest hiring ... We talked about a lot of tactical hiring mistakes that you can make today in sales. The biggest strategic mistake you can make today in sales because there's so many veterans, there's so many folks that worked at Twilio and Mongo and wherever, pick any great company you want. There's so many veterans out there, you just can't hire the ones that don't actually want to sell anymore, and there's too many, there's too many.

LennyYou mentioned that you actually just asked them in the interview. The first question is, "Do you actually want to sell?" What other questions do you ask for either ... Let's go through both. You said you have these questions that you ask for the early hires and then the VP of sales. What are some tips for people when they're interviewing these folks?

Jason LemkinIt's interesting. VP of sales or VP of product, I look for the same answer. One of the Colombo style questions I ask them, and this is so odd. It barely even counts as a question is, what do you want to do your first 30 days? What do you want to do? Actually, I usually ask, "What do you want to do your first two weeks?" In B2B, if I don't hear from the VP of sales or the VP of product that I'm going to go meet customers, out, I'm out. There's too many VPs of product too, Lenny, that don't want to meet customers anymore either. The majority of VPs of products that I interview, they don't meet customers. Every single great VP of product, chief product officer I've ever worked with in my entire career, you know what the first thing they do in the first two weeks? They're like, "Leave me alone. I'm going to go talk to 20 customers. Leave me alone."
The first two weeks, they're like, "Leave me alone. I'm going to go talk to 20 customers. Leave me alone. Leave me alone, I'm going to go talk..." They don't want to sit out on meetings and look at PRDs and talk out of their navel on endless internal meetings. All the best ones, they say they just leave. They literally say, "Leave me alone. I will see you in two weeks. I'm going to go meet with 20 customers." And that's what products should do. Sales, whether it's prospects or existing customers, it can vary, but they should be like, "On my first day, I want to join five calls."

And when you hear that story of, "I don't want to travel out of Pleasanton," or they say, here's what you're going to hear from the wrong person for anything, even up to 50 million in revenue, "I'm going to spend that first month working on process," "I'm going to spend that first month getting Salesforce up and running," "I'm going to send the first month on territory planning, Lenny, because we really, with our three reps, I really want to make sure we've nailed territories, right? Lenny will do the south, Elaine will do the east, Jason will do the west."
When you hear process, process, process, from any, from marketing, product, sales, customer success, too, boy, it's the death of customer success. It's just... And it's not that you don't need process, it's just, it's even worse than it was than a few years ago. And I know this is going to trigger some people, but the truth is they don't want to work. They don't want to work. They don't want to work.
I literally just got this LinkedIn email to work with me at SaaStr, from this person who'd been reading SaaStr for eight years. You're like, "I want to run account management, customer success for you. Here's what's, you're doing wrong, here's how to do it." I'm like, "Oh, this is pretty good." And I DMed her back, I'm like, "Great. To be honest, you realize that you're actually going to have to talk to customers and sponsors yourself in the beginning." No response. Just out. Just out. And that was the best one I got the last 30 days. That was the best inbound that I personally got.
I know it sounds triggering or critical, but as founders, we have to be honest that there's this vast pool of veterans with great LinkedIns and great resumes that are so burnt out, Lenny. And let's not blame them. I know it sounds like I'm blaming them or being negative, and I'm trying to not be negative. I'm empathetic. I am empathetic to the burnout, but don't, you can't hire these. There's too many.
The industry is littered with the burnt out. They're littered with it. And if you hear a touch of cynicism, if you hear anger, if you hear, "I don't want to meet customers in any..." and I'm going to say any VP role, product, sales, marketing, customers... If they don't want to meet customers their first, let's make it a 14-day test, you know they're never going to want to meet customers.

LennyThese folks that don't want to do sales that are VPs of sales, I imagine when you're further along, that's more, okay, because you don't need them to be doing sales, right? They want to manage, optimize. No. I see you shaking your head?

Jason LemkinI mean, okay, you think, okay, there's an element, let's call it north of 50 or 100 million, where for, what's sometimes called commercial sales, SMB sales, it really is all process. Okay? So for sure, I agree. But at Salesforce, they're trying to close $100-million-plus deals. You think that the sales leadership doesn't need to be in those deals? You think they can just hit refresh on the dashboards and track them from home? No. Marc Benioff today is still flying to meet customers. He said the other day, why does Marc Benioff go to Davos? He sits, and I've never been to Davos. He sits at the same place, at the top of some staircase. Okay?

And Salesforce drops millions of dollars, and he waits to meet customers, prospects, and partners in person all day, because it's efficient. Because it's efficient. Because he can do 50 or 100 customer or prospect meetings a day at Davos. He's still doing it at 30-something billion in revenue. Right? So this idea that, is there some truth at... For example, when I worked at Adobe back in the day, it is true that Adobe, which was, parts of the business, sales literally was dashboards. I get it. Okay, at four billion, 10 billion in revenue, but most of your audience is not ready to hire at four billion or 10 billion in revenue. They're not ready to hire that person. Don't hire them, right?

LennyI don't know, maybe Satya's listening. You never know.

Jason LemkinI think on the sales side of the business, they're flying out to the big deals?

LennyTo close the loop on this thread, when you're interviewing the early sales reps, those first two quirky folks, what are some questions and ways to know if there may be a good fit? You mentioned one of, you feel like you would buy from them?

Jason LemkinOkay. The one, really, the simplest one, and early in my career, I thought this was silly or hated it, this Glengarry Glen Ross. I don't know if it was Glengarry Glen Ross or that toxic Leo movie about sales, which is still entertaining. Yeah, one way or another, Lenny, it's got to be, "Sell me this pen." But it's not "Sell me this pen," it's "Sell me this app." So I don't like surprises, I don't like games. I like to do this in a second interview or whatever. Give them time. And I don't like to judge too harshly, but whether it's the first interview or the second, they got to sell you this pen. They've got to put in the 30 minutes of work and maybe it's two hours.

But here's the thing, today's world, you can go on YouTube or someone's website... There's an explainer video for every product under the sun, isn't there? I am shocked how many salespeople I have met, Lenny, from SDR to SEB of sales that, by the time... And I'm doing an interview for a portfolio company, this isn't a screener interview, they haven't even watched an explainer video yet. I could be the fifth or eighth interview, and they don't know how the product works. They have not even gone to the effort of searching YouTube or the homepage and watching it.
And forget about explainer videos enough. But so many companies do webinars now and they publish them on the... Really good stuff, customer testimonials. Right? If you're a sales rep, you don't actually have to know how the webhooks work or how to provision an API key, but you need to know the product as well as that webinar that's on YouTube. And 98 out of 100 folks won't bother in an interview. They won't bother. They're just going to click on "Apply" on the ATS and tell you, "Hey, I recently stumbled upon whatever. It looks like... Do you have time to discuss." Right?
But that one that actually does enough work and watches the video, and then can sell it to you, and they're going to make mistakes. They're not going to get it right, but they have enough confidence with the core problem to be solved. Because here's the mistake that 99% of founders and sales reps make. We're not really selling in B2B. We're solving problems. And this is why so many people are struggling in 2024, because they can't... their products, as sales reps, as companies, they can't solve big problems anymore.
Our job as sales reps in SaaS is to not sell a used car, okay? We are selling a Tesla Model 3 performance. It has competition. I might not need it this week, but it's pretty darn good. And I'm going to help you understand, Lenny, because you're in the market for the car, why this is the best one. I'm going to be honest about where it's not. I'm going to answer all your questions. I'm such an expert, and then I'm going to ask you, Lenny, when is that... You have 280,000 miles on the Civic? Let me help you get you into that Model 3 performance today. And I've even got a special discount for the end of this month. And let me just help you."
And I've spent four calls answering all your questions and I'm explained to you all the things and why the supercharging network is better than the regular one that doesn't really work at the charger near your house. And I've gone on Google and I've seen there's no charging network near your house, there's only supercharges. I got you, don't I? And that's the job of SaaS and sales, because we're not selling commodities. And that's why the best reps will also tell reps when not to buy their product.
As painful as that seems in tougher times, in 2024, the best reps say, "No, we're not there yet. We're not the right... If you need this feature, if you need this integration, I want you back in six months when you use this big product that isn't that great. But today, we're not the right solution for you." That's, the best ones do that. They have the confidence to know to close it. And the rest of the world thinks this is some sort of adversarial transactional thing and it's not. Right?
Software... I think hopefully all your audience would agree, when it's done right, software's magical. It solves incredible problems, incredible problems. What Airbnb does, what Uber does, what SaaS... Things solve... I can track my customers, I can manage, I can automate my communications. It's magical. You shouldn't have to use boiler room tactics and use tactics when you have something. But, it doesn't sell itself, except for a little while in late 2020, early 2021, that screwed the whole world up when products actually sold themselves.

LennyI feel like this is a separate podcast we should do of just how to get better at sales and how to sell. But, I feel like that's its own hour of conversation. I did a great episode with April Dunford where, I don't know if you follow her stuff, but she-

Jason LemkinYes.

Lenny... essentially describes exactly your approach of help people understand the market, help them understand the entire landscape, and then talk about your problem. So anyway, we'll link to that episode. Has a lot of good advice there. In terms of this interview, selling-me-a-pen approach, to give people something very concrete to do. How do you actually set this up? Is it like, "Sell me your product," and then they put together a pitch for your team and they pitch you on a product?

Jason LemkinI'll tell you, until the boom, until everyone in late 2020 got so desperate to hire anyone with a pulse, almost everyone in sales had to come and they had, during an interview process, they actually had to do the pitch. They would come and you used to do it in person with this screen. You can do it on Zoom now, it really doesn't matter, but do it for real. Do it for real, and everyone would see. And everyone in recruiting change, people stopped doing reference checks, they stopped doing these tests, and they would just hire warm bodies.

Late 2020, I can tell you a funny story in a second, and it was okay until it wasn't. And our hiring processes have not reverted back to pre-March, 2020, and I think it's failing founders left and right. I can't tell you, I would say 95% of the hiring I see out there, people don't do reference checks anymore, Lenny. And we can talk about when they work and when they don't, but no one does them. No one does them. You're going to invest so much... Forget about the salary, it doesn't really matter. So much time, your time, your leads, everything's so precious, to bring Jason into your company and you're going to go through all this recruiting process and you're not even going to do any reference checks? People don't even do reference checks.
And they don't, they stopped doing, "Do me this demo," because they were so worried the rep would go to Gusto or would go to Deal, or would go to remote. There was no time. I got to get... This SDR has 50 offers. Lenny, we got to hire this SDR with three weeks of experience. We've got to decide today. And that's the way, and hiring does not come back. If those hires bounce, not only is it bad for you, but it's a disservice to the... It's worse for the hire. I mean, that poor CloudFlare woman that blew up with the thing, there's so many issues there we could dig into, but it's all Cloudflare fault for hiring her. Okay, let's forget about that she didn't close a single deal. Okay, so objectively, in sales, should you retain your job in sales if you can't close a single deal? I don't want to get into some of the triggering things, but remember, if you hire someone and they fail, it's all your fault. She didn't know what she was getting herself into. No candidates can do enough diligence ever. There's not enough time. There isn't enough time.
And this is true all the way to the top. And so, as an investor, a board member, it's funny, when I do interviews, I do this thing, I try to be the last interview sometimes, and the founders don't want me to do it. They want me to sell. I don't want to be the last one. And what I want to do is when, Lenny, you've decided to join Ellen at her startup, right? At the end, I said, "Look, Lenny, I've talked to Ellen, she loves you. You have the job. You've got the job. What I don't want you to do, Lenny is bouncing three months after. So let's slow down, let's talk about the questions you have on your mind, and let's have a safe space where we can make sure you're going to be happy and successful there." Right?
And sometimes even the founders get mad at me for doing this, because sometimes, the candidate bails. But I'm like, "I know you're mad at me today, but it is your fault. A hundred percent your fault if any of your hires fail. Don't blame them. And I'm guilty of this. I get upset when people start and they don't give it their all or they don't do it. I mean, what if you hired someone for your podcast and they decided, "You know what? I don't want to do the podcast this week. I'm tired. I'll do it..." You're so mad at them, but you should've seen it during the hiring process. Right?
So, tying it back, that's why you've got to do this, "Sell me this pen." You've got to, before you hire the salesperson, have them sell your product real. Do the demo. And if they need more time, give them more time. Let them watch another demo. Don't have them feel like it's a trap or spook them. Treat them the way you would like to be treated. But if you skip this step, I mean, what's the point? You're not helping them.

LennyWhat I love about this process is it connects exactly to what you recommended you look for in these hires is, "Would I buy my product from these people?" So this makes a lot of sense. And you give them this assignment at home and they do work on this and they come in, right? It's not like come to the office?

Jason LemkinIf you talk to a great transactional VP of sales that's hiring tons of reps that do it, they'll make them do... If they're still doing this, they'll make you sell the pen fast in the process. They don't have time. They're doing 20 interviews a week, 30 interviews a week, you've got to sell me this pen. But if you're a founder and I'm talking about you've already talked to a bunch of candidates, you're down to one or two, make them, tell them, "Look, this isn't a trick. I'm not that great at telling my product myself, but I got to know that you're going to be happy and successful here. So do a demo for me."

And if they won't do it, they're not a salesperson. And too many people went into sales, not... The other weird thing about B2B sales in good times is actually, a lot of these folks are not really what you might think as salespeople. They can't do outbound, they can't pick up the phone. All they know how to do is to manage leads that come in and say, "I want to buy today." And you need those people, too. Okay? And I'm not saying you don't need those people, too, but that's not always what we think of as sales.

LennyAnother black box for me, and I think a lot of people with sales, is comp and quota, had actually set up their comp for early hires, and then how to actually decide on a quota. What advice do you have for figuring that out early on? What percentage is commission, what percentage is salary? All that-

Jason LemkinYeah, everyone gets this wrong. We worry... Look, at scale, when you're extremely mature, extremely mature, and very profitable, you really got to tweak this stuff very carefully, and we could talk about that if it's relevant. But, in the beginning, we get this all wrong. What matters is, can a sales rep close more than they take home? In the very beginning, that's all that matters. It's just you selling, right?

The first three months of a new rep, you're lucky if they can close as much as their take-home pay is, their OT. And so, in the really early days, my early, early day comp plan is, look, your first three months, you keep a hundred percent of what you close. Of course, that's not profitable for the business, but you've got to invest in them, right? You keep a hundred percent of what you close. And if you have enough going on in your business, usually, that's enough to put supper on the stove.

LennyAnd that's without a salary?

Jason LemkinNo, no. You pick an OT, a salary, but you got to... Okay, let's step back for a minute. You got to pay market. You got to pay market. And in the early days, if you're bootstrapped or really lean, this stresses folks out. I just talked to this great rep, Lenny, but he wants 150k OTE. And in fact, it's a step down. He had 170k at Slack, but he knows this isn't a startup. He wants 100. He might take 140.

LennyAnd OTE is total comp, overall total comp.

Jason LemkinTotal comp. And the founder panics. "I don't have, I'm only making 60. How can I pay 140?" Well, let's break it down for a minute. First of all, let's be tactical. It's usually 50/50, right? 50% base, 50% bonus for a sales rep. So they're really only taking home a 70k base, trying to make another 70. Okay? Then 70 divided by 12, help me do my math. It's not quite 6k month. Well, maybe with taxes it is. You're really only paying 6k a month for a couple months to see if this experiment works out. You're investing 20,000, you don't have $20,000 to do sales? Then don't do sales, if you can't find $20,000. So people freak out too much about this comp-line number, this base and bonus, the on-target earnings, OTE, and they're not more practical about what am I committing to cash upfront?

Two, you need a plan where it's a win-win. So if this person makes 140, but ultimately, a sales rep's got to bring in four to five times what they take home. That 140's got to be 500, 600 or more. The more enterprise you are, the bigger the multiple has to be, and the higher the comp. But it's got to be 3x to 5x at a minimum, 3x for small businesses, 4x for mid-market, 5... You got to get there, but you don't have to be there on day one and two. When you get there, the reps should be accretive, shouldn't they be? If they make 150 and they bring in 450, unless your marketing costs are out of control, which can happen, but that's not sales fault is it? If your marketing costs are reasonable and you pay a sales rep 150 for closing 450, if you engineer your plan right, you should be smiling, not frowning.
Where it gets tough is when you have a ton of folks not closing. When you have a ton of folks not closing and you have extremely high marketing costs, then it all breaks. Your cap breaks, your payback period breaks. But, if you have inbound leads, if you have demand, and you have sales reps that can sell you this pen, they're going to be accretive, Lenny, because of that math. And take the pressure off, don't make them close 5x their take on their first quarter, make them close 1x. Let them put points on board, let them eat. And so negotiating, here's the point if you think about it. Negotiating someone down from a 150k OTE to 130, it's not going to make any difference. You want them to close 600 or 700. It's not going to matter.
At scale, does it matter? For Mongo maybe. Maybe. But, what you care about is how much more can they close and they bring in? And then you, that's why you want them to make a lot of money. You want them to be rich. You want them to take home a lot for a whole bunch of reasons. And so, don't freak out about the acronym OTE, what they take home. Figure out what it's really going to cost you and would you buy from them? And if you would, they're probably going to bring in more than they take home. Right? And on the marketing side, in early days, you're lucky if you can find a marketing channel that is that accretive.

LennyAmazing. Okay. So just to summarize, you start a sales person with, say, 75k in salary and then say 75k in expected sales. And they take-

Jason LemkinBonus, bonus.

LennyBonus.

Jason LemkinBonus from sales, yep.

LennyBonus from sales and the the idea there is they take 100% initially of their sales, for the first month or two, just to make it feel amazing. They're making money. See how they're doing, don't put a lot of pressure on them. And then the plan is, over time, get it to a point where they're bringing into the business four to five times what they're taking home in terms of bonus.

Jason LemkinYeah, yeah.

LennyI set expectations every month or two, or is it every quarter? We're going to revisit your comp and quota and adjust.

Jason LemkinIf you get it right, you never have to revisit it. Not for years. I mean, I'm using the same sales comp plan I have for a lot of years. It still works. Listen, you can make tweaks and you've got to listen, and we're all human beings. And people, and again, remember, your sales team has to eat. They've got to eat, okay? And you've got to be somewhat competitive. But, there's only so much you can tweak, Lenny. I mean, they have to bring, close more than they bring home. Right?

And so, you can make tweaks at the margin. The problem is if you make too many tweaks to this model, you burn up all the cash. You're trying to plug a leaky boat, there's no point. There's no point. There's no point. And remember, related to this, for a long time, for most folks, unless you're, even if you're hyper funded, you're better off with fewer, better reps than more reps.
There is a stage when you get big enough where this concept of capacity planning really does matter. Lenny, if I got to go from 50 to 100 this year, okay? I'm going to add 50 million. If each of my reps can do 500k, I need a hundred, don't I? Okay. And literally, if you have 20, you mathematically cannot hit the plan. So there's a certain truth at scale. In the early days, this is a rookie error. I'd much rather have two reps, each closing a million than 20 reps struggling to close 100k each. Culturally, it's terrible. There's no domain knowledge in the company. Everyone's miserable, everyone's fighting.
What you want to do in the early days is concentrate your leads and your best closers, at the same time, bringing new people up. But you've got to concentrate your leads to your best closers. And that means year two, year three, year four, they should be making a lot of money. Lot of money, sometimes too much. I remember the first investment I ever made was a company called Pipedrive, which sold for a billion and a half. SMB CRM, and I put in the first sales rep there. He used to work for me. And the founders got mad at him. They got mad at him, because in three months, he was making more than any of the founders. They were pissed.
I'm like, "Guys, I know we're have different backgrounds and cultures, but this is what you want." But it took them a long time culturally as self-serve... Because Pipedrive was 100% self-serve at the time. They'd never had a sales rep. And I put the guy in, and what he did was he went and he looked, all these self-serve customers, he's like, this was the company was about two million revenue at the time. And he's like, "Okay, who's bought more than one seat?" He just did a reverse sort and he called them.
I remember he called AOL back in the day and he's like, "You guys have 20 seats of Pipedrive. Would you like to buy more for your sales team?" They're like, "Thank you very much. We'll take 100 seats." And he just went down the list, from the top to the bottom, and he took home 20% of those deals. Now that difference, that extra 80 seats at AOL, he brought it in. So Kim, keeping 20% of that is a great deal for the company, right? But he was pretty good at it and he was the only person for a while, so he made hundreds and hundreds of thousands of dollars when the poor company, the founders were paying themselves 50.

LennySo your advice there is don't be sad if your salesperson is making tons of money.

Jason LemkinIf you architect the simple sales fund we talked about, and they're making a lot of money, you're making a lot of money, and your equity is worth a lot of money, your equity is worth a lot of money. Right?

LennyWhen do you make that switch from they're taking home 100% of what they're selling to smaller percentage?

Jason LemkinLook, some people are going to think it's goofy what I said about 100. I just view it as a simple ramp. I think you do it for one quarter max. One quarter. The problem is if you let this go for too long, more than a quarter, if you make it too easy for long a quarter, the problem is the mediocre lean into it too much, and that doesn't help. And not only does it not help you, it doesn't help them. You don't want to make mishires. They're so damn... I mean, you could have a whole podcast only just on mishires. It's probably the single most important thing in scaling startups. It's not hires, it's mishires.

It's a tragedy if you mis-hire a rep, but you don't want them there six months. It's not good for them either. You want to support them, you want to help them find a place where they're successful. And here's the quirky thing on the mishires, and this is why that first guy I hired was mid-pack. He was less than mid-pack. Here's the thing about sales is, someone can be very good in certain sales environments and completely fail in other ones, completely fail. It's probably more binary than any other function. And so you got to find it before you hire them, but you also got to root it out fast, because those leads are too precious.
And it doesn't mean they won't go on to another company and be wildly successful, but you could utterly fail. And the one related point I'll give, if I had to throw one hint on this first, any of these reps, first 10 and VP of sales, one hint more than anything else, trust... got to hire someone whose last product was harder to sell. This is so important. This is a recipe for utter disaster. If you've, take someone in sales and their last product was easier to sell, they will have none of the skills to sell your product. But, this is the... and I'll give you an example in a second.
If you hire someone from something that was just a smidge harder, a smidge harder to sell, and they come into your company, it's like they're on Mars. It's like weight has been released from their feet. They learned how to sell a harder product and get it done, and then they come to you. And the first example I had, the first SDR I hired was a guy named Sam Blond, who went on to be CRO at Brex, and then now is a partner at Founders Fund. We worked together from the very beginning, first SDR. And he came, before that, he was an SDR at a company called Intacct, which was bought for a billion, which was online financials. Okay?
And back in the day, we know what the one thing people didn't want to put in their cloud was? Their financial statements, okay? It just wasn't trusted that. There are some things you would trust to the cloud, like A CRM, but they'd be like, "These are my crown jewels. I can't put these..." So he went from desperately trying to convince folks to move a business process to the cloud. They had no interest. And he came to us, and it was hard, but it wasn't that hard. And he instantly was number one. He went from SDR to SMB-AE to mid-market AE to director of sales, to head of this whole sale...
Because, I mean, there are many reasons he was great, but he came to me and I said, "Sam, why are you crushing it when everyone else here is struggling?" He's like, "This is much easier than Intacct." So hire someone like that and don't make... No matter how much you like them, the sell me this pen thing will control for it a bit, okay? But, when we give, we give, we give in the hiring process. We never give what we want. Be very, very careful if the last product was easier to sell.

LennyI love this advice. What is a heuristic that the last product was harder to sell than yours? What tells you that that's probably true?

Jason LemkinBe very careful if it was more technical, very technical. Some folks can go from a business process sale. They can go from selling a Gong or a sales software and outreach, and they can go sell a complicated API to VPs of engineering or VPs of product, but most can't. Okay? So more technical is a tough heuristic. More competitive is a positive. What really works, Lenny, is if you hire someone from the number four in the space and they did well. You take someone that was number four in the space and then you're number two in the space? You think number two's really hard because number one's crushing you? But they're at number four in a space where no one can tell the difference between these products? That's a great one, right? So a space that's more competitive, a space that is a positive, more technical.

The other one related to technical, on the pure B2B side, is much more complicated business process. I see folks fail in B2B when they've sold us... Yeah, it's hard, but they've sold a simple business process. They go to something that's got a lot of integrations, a lot of complexity, and a lot of business process change, and they just melt because it's too complicated. They just melt, right? There's a company I invested in, it's doing over 20 million today. And for some reason, to simplify what they do, which is pretty complicated, they called it the Gong for X. Okay? The Gong for X.
And it's great to get a VC meeting and a few other, but it's not even on their homepage, okay? It doesn't really make sense. And the CEO had me listen to this senior sales exec he hired, and the only thing he could tell the prospect was that they were Gong for X. And the prospect kept asking, "Well, how does this deep integration with this business process flow and Zendesk works, and how does this go over to Salesforce?" He's like, "Well, we're Gong for X." That $600,000 deal was lost. Right?
But, maybe that works in some space, right? And Gong's hard to sell today, too, don't get me wrong. But you see my point, it's just that simplicity, it's too complicated, right? And I know it's not the perfect heuristic, other than this technical thing, but the technical one, man, trust me. Too many B2B type reps melt in B2D. They just melt. They just, selling to VP of eng is a different... It's the same beast, but they don't suffer fools, do they? Not the VP of engineerings I'm close. They don't suffer fools.

LennyI haven't heard this term, B2D before, business to developers.

Jason LemkinTo developer, yeah.

LennyI imagine that what it stands for. Oh, interesting. Haven't heard that term before. Okay, let me zoom out a bit and I want to move on to a different topic. But before we do that, so we've talked about kind of these early days of hiring your first two reps, getting your VP of sales to help scale out the team. To give people a sense of where this goes, as the business scales, what does the org evolution look like? You have these two reps doing sales on their own, then you have a manager. What does it look like over the next couple phases of the sales org?

Jason LemkinLook, to simplify, there's rules of eight. So in sales, I'm actually not sure what the tip of heuristic is in product, because product teams are leaner, at least I hope. I like it when they're leaner. But the thing about sales is there's no efficiency. If you have a sales-led motion, half your company is going to be in sales at 10 millionaire, half your company is going to be in sales at 50, half your company is going to be in sales at 100.

One of the tough parts of the software model is that there's no, there's actually almost anti-efficiencies in sales. The public companies are actually less, they have the higher CACs than startups, believe it or not, because they have so much market penetration. So you're going to need a lot of people. And it's rules of eight, eight SDRs, outbound reps need one manager, eight AEs, eight sales execs need a director above them.
And then when you really scale, eight directors. You don't really ever going to have eight directors, but eight directors could have a VP or eight reports. And so there's rules of eight. If you want to build an organization on it, it's all rules of eight. For a while, for SDRs, thinking this was this high velocity entry-level position, people pushed it to 12. But the more folks I talk to today, the more I hear, everyone's reverted to eight. I'd rather have fewer SDRs, having better conversations. And so it's just, you can build your whole org with eights.

LennyThat is way too easy of an answer. So the idea there is you hire this VP of sales, then you hire six more sales reps, AEs. So what happens next? You hire another-

Jason LemkinGot to start hiring managers.

LennyManager, got it. Yeah.

Jason LemkinYeah.

LennyAnd then you scale eight more reps.

Jason LemkinAnd once you have eight AEs scaled, you almost always are going to start, a VP's going to already... A good VP of sales already be hunting two directors.

LennyTwo directors.

Jason LemkinWhether they're just split up normally, whether they're east, west is a classic way. Another way, you might have smaller and larger customers. That's pretty standard, right? Commercial and enterprise. But a good VP of sales, once you have, she or he has eight reports, will be bringing in two directors, or maybe two VPs if they're an SVP. There's a lot of title-
... directors or maybe two VPs if they're an SVP. There's a lot of title inflation today, which doesn't bother me nearly as much as a lot of other things we've chatted about. I don't care what your title is if you'll actually do sales or do work, but yeah, we need to bring in managers at 8:00. And folks that can, also, a related point is, a lot of founders were, "When will my ... " I really love my head of sales, but she's a stretch. Most of them should be stretches.

If you hire the seasoned one, they're not going to work, so for 95 out of 100 of us, our first head of sales should be a stretch VP of Sales. And what that means is, usually, they were a director before that or a senior director or sort of a VP, okay? But you should be cautious about hiring your first VP of Sales for their first third VP of Sales gig. They're not willing to do the job anymore. You need a stretch and it's worth it for their career growth. It's worth it for their personal growth. It's worth it for the equity, right? So you're going to hire a stretch. That's an important tip right there. But then, you're going to be a little worried, how far can Lenny go? How far can ... I love Lenny, but he was a director for two years before this, and this is his first rule, and he did so good last year, but I'm worried Lenny's going to break. I'm worried Lenny's going to break.
And related to this quote, the simple answer is, Lenny will break if he can't source those directors under him. You can scale forever as a sales leader if you can hire better managers under you. And it's true of any functional area, but what you'll see in sales is, you'll see your stretch VP of Sales drown when they never can hire better managers under them, They'll end up doing some weird internal promotions, which you want, you want to do internal promotions. My rule is you want to promote 50% from within and hire 50% without for your managers, but if, really, the only people you can promote are just junior people on your team, you can't find leaders, you can't scale. I do see this happen too frequently is, a first time out of sales, does it, and then, they're like, "Here are my managers, Lorraine and Jason, but they really were just reps for two years and they don't know how to do it." So you have a whole bunch of people who don't know how to do it. That's when the organization cracks.

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There's these terms that we throw, around account executive reps. It might be helpful just to give people a sense of what does this actually mean when someone's an account executive. Is it that they're just sitting there calling and doing sales directly? Whatever the key terms are for the roles or the title might be helpful to quickly summarize.

Jason LemkinYeah, I think the two ones that are probably less obvious for folks that are new are SDR, Sales development representative, and AE, account executive.

LennyOkay, great.

Jason LemkinAnd SDR is, generally, although I wish it wasn't, it is generally an entry level position, often fresh out of school, generally paid on the order of 60K to 80K, OTE and SaaS and US-based SaaS, and their job is to email for dollars, dial for dollars, and in many cases, to screen, to screen inbound leads. It's entry level, and their job is to pass on a lead to a sales executive, an account executive, an AE. Not all companies have SDRs. It's a longer topic, but pretty much all the best teams have some type of SDR function now because we've learned we want to specialize. We want openers opening and we want closers closing, so that's the rough idea.

SDRs are openers in some cases, and account executives are the more seasoned folks closing. And it varies, compensation from account executives that are US-based could be anywhere from like 90K to 200K, depending on, that's with base and bonus split at 50/50, depending on whether they're hunting tiny deals or big ones. That's the way an account executive works. And I think what doesn't happen today ... Those are the acronyms, SDR and AE. I think people can figure out VP of Sales, that's vice president of sales.
I think a thing that's gone on in the industry that founders expect now because there's so much discussion of it on LinkedIn and social media, but I haven't found work, is that an account executive will magically be full stack. They will do outbound themselves, they'll go use ZoomInfo and Apollo and develop a list themselves, they'll manage that outbound list themselves. If they don't have enough inbound, in their free time, you know what they'll do, Lenny, in their free time? They'll just do more outbound. You know what sales reps do in their free time? Today, they sell real estate or courses.
If you want a tip, for founders, I know you want this full stack AE, and they do exist when they're micromanaged in certain high performance sales organizations, but they don't exist in real life. They're specialized. Most AEs, they want to be closers, they want to be handed a lead, a contact me, a lead. They want to work the lead and close the lead, and you hire some SDRs to help generate more demand. Those are the basic acronyms. What's hard for most founders, here's the tough part, most founders have enough stamina to manage a couple of these AEs, these account executives, these folks who work the leads. Most founders do not have the stamina to manage 10 kids fresh out of college that need to be micromanaged on an hourly basis to call leads. Very, very few founders themselves can manage a team of SDRs, but if you can, it's like a superpower.

LennyThat was really helpful. I did not know what exactly these terms represented, and when you're hiring those first two reps, they should be at the account executive level.

Jason LemkinYes. And they'll do some outbound and they'll do some of this SDR work. It's just, ultimately, people end up specializing.

LennyWhat is the title for someone above the account executive? Is it Director of Sales?

Jason LemkinYeah. There's really no ... It's a meta topic. I wish there were another career path for these ICs. This does exist in product, it does exist in engineering. It should exist in sales, but the truth is it doesn't. There is no senior SDR for this outbound. And for this AE, this person closing, yes, you can go more enterprise and make more money, but there isn't really a senior AE track, but there should be. It's unfortunate. It should be.

Too many of these folks are looking for, they look to go into management for promotion when what they really should look for is to be a super IC, and it's a shame that more folks don't try to implement a super IC role in sales, but that's basically what the career path is in management. And that's why another tip, another mistake that founders often make is, they hire the number one account executive at a hot company to be their head of sales. It's not the same skills. Most sales executives should not be managers. They don't want to be managers. They want to be individuals. They want to be highly paid individual contributors, these days, that mostly work from home and make a lot of money working 30 hours a week. That does not naturally breed great management skills.

LennyI want to shift directions a little bit and talk about product and sales. A lot of listeners of this podcast are product managers or founders building products. How involved should product managers be in sales. And vice versa, how involved should sales be in the roadmap and what's being built?

Jason LemkinI think, in the best run B2B organizations that I've worked with, and my own as well, the great, at least the head of product, the VP of Products, are deeply involved in sales. Deeply involved in sales. Deeply involved in sales. A company I invested in that's just crossing $60 million, they just had a meeting with who will be their largest customer. And the head of product who was there at the board meeting is like, "Thank God I was there because what they want to do with our product, we sort of do. We sort of." Now, the product does do it, but what they want to basically do is deconstruct the product. They don't actually want to use the backend and analytics and some other pieces, but they don't really need the front end of the product. If the head of product hadn't been there, that deal would've been lost. It would've been lost.

An AE doesn't know that. Even if an AE did know that, a sales rep did know that even. If the VP of Sales didn't know ... A VP of Sales would not be empowered enough to stand up in a meeting and say, "I know what you want. We can launch tomorrow on this and, in 90 days, we'll tweak the UI so it does exactly what you want." You want that in your big deals. If you have that magical VP of Product that truly owns the roadmap, owns it and has the gravitas for that meeting, they become like the mini CEO in these meetings. A lot of CEOs, at scale, I've talked to, I was just talking with Daniel Chait at Greenhouse, he does this, they're over $200 million, when they have that head of product, they divide and conquer with the big customers. And the CEO can do some and the VP of product can do others.
And sometimes, the VP of Eng, if they're very producty, can also do that role too. Sometimes, you get these three weapons. In the old days, sometimes, your VP of Customer Success could do this, but unfortunately, and I know this is going to trigger some people, I don't see customer success stepping up for this pseudo product role anymore and I see them shrinking more and more into process. But that magical VP product, they give you that scale, that CEO level scale.
Can a product manager or a director do that? In my experience, the best ones, absolutely. The mid-pack ones that are working on the color of the pixel, I'd rather not have them in the deal. You have to be utterly fluent in the product, the entire product. You have to be the one that knows how to connect the pieces that don't ought to always connect themselves, and you have to have the gravitas to work with a large customer, to make commitments. That deep knowledge and commitment, it's hard below the VP level, but if it does exist, I love it. They become one of the greatest strategic weapons of a B2B company is bringing the product team, because the VP of Sales never quite goes that deep and can't make the commits, and the CEO can't be everywhere.

LennyThe bane of many product managers' existence is the flip side of sales is involvement in product. Do you have any advice for how you've seen the best SaaS companies handle requests from sales going into product, how product teams should think about requests from sales and making that work?

Jason LemkinI think this one is so simple and I'm surprised people make it so complicated. I know we all release 28 times a day, but the reality is, software still goes on quarterly release cycles no matter what we say, okay? Your customers cannot process 88 releases a day, okay? The maximum a customer can process is two big releases a year and maybe quarterly, so let's simplify. That's how customers think. Forget about how we build software.

Every quarter, give your head of sales a certain budget, whether it's story points or 10% of the pie chart, however you do it, give them a budget. And when you do this, things will radically change then. They radically change because even the best VPs of sales, they change the wind. On Monday, what they really need is the HubSpot integration. And they're like, "Oh, my god. We weren't going to do that for two years, but I guess we could change everything on Monday," but then, on Wednesday, a new prospect comes in and, "We need SAP, but we just spent two days spec-ing out." You need SAP. And then, on Monday, it's Salesforce, right? And it's not that sales isn't honest, it's just, the big deals, the big ones always, the tail's wagging the dog and it burns out the organization. Even with the best sales leaders, I find it burns out, especially because the stressful deals, they overreact, and as good as they are, they're not product people, so they don't really know how to prioritize and force rank. If you say, "Okay, Lenny, my VP of Sales, great. HubSpot, SAP, whatever you want, you've got 10% of the budget, you've got a hundred story points, whatever metric or heuristic you use, but you've got to decide now each quarter." And if you want to change during the course of the quarter, if you want to disrupt our whole engineering product team, you can do it, but understand there's a high cost, and the later you do it in the quarter, the less successful it's going to be because we already started the HubSpot integration. Not only will it demoralize the team, but we're going to run out of ... You already used your budget.
I just don't see enough product leaders being objective here, saying, "Listen, here's your budget. You get it, period. No one can take it from you. I guess the CO can steal it if she really wants to, but it's yours, VP of Sales." And they will do the low balancing across their team. They will do it. They will listen and they'll say, "Maybe I don't need that HubSpot integration after all. Maybe." Right?
Because what a VP of Sales should be doing is taking ... The CO has to look five years into the future, product has to look about two years into the future, and you really can't ask a VP of Sales to look more than 12 months into the future because that's where they're next on the line, but a good one will load balance feature requests across the year and they will listen to all the ... Because they'll actually be in sales, they'll actually be in deals, and they'll be listening and they'll realize, look, even though we're going to lose this deal to HubSpot, I've gotten four SAP requests the last ... I'm going to take that bet. Even if I'm wrong, I'm going to take that bet. You got to give them that ... And you got to talk about it every week and say, "Look, here's your budget, Jane. Here's your story points, your whatever, your 10%. This is what we're building now for you, objectively, and this is what we're currently planning for the next two quarters. Would you like to change the ones for the next two quarters? Because we haven't committed any code yet, and if you really want to change what's in process, you can. Otherwise, it's going to be hyper disruptive," but you got to at least pretend to be objective, for sales.
If you're too emotional about it, you break the organization. You've got to say, "Listen, I know we've already written 80% of this upside integration. If you really need us to put us on the shelf and drop everything for a million dollar deal, we're a startup, we'll do it. But understand, just, is this really really what you want?" And if you involve them every week as a stakeholder, magic happens. But I don't see the VPs of Product that I work with, I know I'm not in all the staff meetings, but the meetings I'm in and the board meetings, I don't see this back and forth happening.

LennyThis might be the same exact answer you just gave, but say you're a PM and a salesperson comes to you, "Hey, we're about to close this deal. We just need this one feature. Can we just get this on the roadmap?," what's the best way to help that sales person understand why it's not happening, help them feel like, "Okay, I get it"? Is it exactly what just said? "Okay, we could change everything. Here's the story points you have this quarter."

Jason LemkinWell, are you assuming that PM is the head of product or empowered enough to make the decisions?

LennyI'd say, yeah, that PM could put something on the roadmap if they think it's important.

Jason LemkinThe reason I'm a little confused, just because I want to get it right, is what I'm hearing, which maybe isn't what you said. What I'm hearing is, a junior IC rep is talking to a more mid-level product person about the roadmap, and you want to have that. That's one of the reasons we actually go to the office. Because those discussions don't happen on Zoom, Lenny. They don't happen. And you want those discussions to happen, but you don't actually want them empowered. You want them to say, "Listen, I will talk to my boss." That's the right answer. It's too confusing.

This stress between product and sales is a good thing. It's a sign of a well-run B2B company when there is stress between product and sales. It's a good sign. If there's no stress, you're not in enough deals. You're not in enough deals if there's no stress. But the stress has to have enough process, even in a startup, that it doesn't break because your question alludes to the fact it can break organizations again and again. People get people resented on either side.
This is one thing where the answer has to be, "Look, we can chat about it over lunch. We can chat about this, and actually, you've got a good idea. You're an individual contributor. I'm going to tell my boss, on Monday, that I think we should do that. I'm going to use a little social capital and say we should do this," but you got to push the decisions up. That's as far as you're going to make recommendations. Otherwise, instead of that one stressful conversation with the VP, you've got a hundred, you've got 10 times a hundred, and again, they're fun lunch conversations, but they'll wreck you.

LennySo the advice there is, basically, "Talk to your manager, I'll talk to my manager. They need to hash this out. It's not my call."

Jason LemkinI think you got to push it up and I think you got to force the VP of Sales and the VP of Product to have this weekly meeting about the budget, and that will force them to have enough, just enough organization on their team so that it can all be surfaced up. Because that means they each have to have a meeting with their team for 30 minutes each week and say, "I'm going to put up on the whiteboard guys, so my sales team's going to say ... And I've been to many of these meetings where you force the sales team to force rank what they want and you end up, I tell you, Lenny, 100% of the time in the sales meeting, when you do a whiteboard force rank, you end up walking out with very different outputs than when you start the meeting in sales 100% of the time.

On the product side, you need to do the converse. You just need to say, "We owe sales 10% of our points, so in our team meeting, we're going to put in 15 minutes of our team meeting and we're going to make sure we have the priorities right from the sales team. Let's go over what I got from Linda. This is what she says. Is she wrong? Should we do something? How can we help the sales team be even more successful? And what inputs is the team hearing?" And they can raise their hand and say, "Look, I just had this all the way conversation with Bobby, but honestly, Lenny, I can build a HubSpot integration in a day." "What? I thought it was really hard." "No, I did it my last company. And listen, actually, we can actually outsource it to Bob and Linda at this agency I know for 20 grand. They'll build it next week." That's a magical moment. That's a magical moment. But you've got to each have these parallel meetings. The good thing, that tension can become debilitating. We've all seen those fights, those almost fights that break out, and they come from a place of passion, but you got to have structure.

LennyGreat advice. Another trend I've been noticing is that product teams are taking on P&L responsibilities and revenue goals. What's your sense of, is that good? Is that bad? How do you think about that for product teams?

Jason LemkinYou want everyone to be aligned on the big picture revenue goal for the end of the year. Is the question, you mean having financial bonuses and stuff tied to hitting the plan?

LennyMore that their KPIs and their OKRs are essentially this much revenue, you need to drive this much revenue from your experiments, from your product launches.

Jason LemkinAs you can see, I have a lot of opinions on things here that are data-driven and they're live experience. This one, I need another year in the oven, and I'll tell you why. I'll tell you why. What happened in the last 18 months is, in customer success, which is, in the old days, it was related to product. Now, it's less so, which I think is unfortunate. In customer success, in the last 18 months, this happened all across the industry. 24 months ago, customer success's goal was happy customers, measured in retention, sometimes NRR, net retention with upsells, sometimes with GRR, just logos, how many logos. That was your only job, happy customers. Happy customers.

Then, things got harder in many areas of B2B, and every customer success team last year, their goal was revenue. You need to bring in more revenue from existing base, and it destroyed customer relationships. There is a leading public company, I will not name them, I'm a positive guy. I will tell you, a company we all have used for years and loved, and they did this to their customer success team. And they came to us last year, we paid $299 a month for this product for our team. They asked us for $50,000 upfront or said they would turn it off that day. That week. Maybe it was that week. $50,000. That's what happens when you weaponize ...
So customer success, and I know this is going to trigger some people, but it is true, when I talk to leaders, customer success got weaponized and I don't like it, okay? I don't like it as a product. All founders are product people, I think. I don't like it as a product because I think it's bad for customers. That experience I got was horrific, wasn't it? That $50,000, being told. And it got walked back. And the fact that it got walked back is almost even worse because it wasn't true. It was a threat. So do I want to weaponize the product team? I want the product team aligned with revenue. These are the tough decisions for founders. But I think we're going to regret, to some extent, weaponizing teams that we don't need to weaponize.
Having said that, I will tell you, and again, no knock on Adobe, but when I was a VP at Adobe, and it was a long time ago, when product was in another building, in some cases, that was not great. And I love Scott and the whole team, it was a great experience, but I can just tell you, what I learned is, that did not work for me as an agile guy, having groups that would do this work in isolation.
And the problem was they would never talk to a customer. So I know I want product constantly talking to the customer. I know I want the VP of product with a lot of equity, wanting to hit the bookings number for the year. Do I want your average PM weaponized and forced to bring in revenue from an experimental feature when everyone agreed it's the test we're going to run? We only can run so many. You say, should they have revenue for new feature launches, for new product expansions, for new things? Yes, but everyone's got to make that decision. There aren't that many of us that have 1,000 extra engineers sitting around with nothing to do.
Even the smallest experiment, no matter what it says on the internet, again, that we release 100 a day, I would argue bringing any product extension to market's very expensive and risky because you're taking away from something else. These are expensive decisions, and if you punish people for the mistakes in product, this is something that big companies are actually better at than startups, which is, they don't fire you if the new initiative fails. Because then, no one at a big company would ever join the new initiative. There are exceptions, but no one at Adobe or Google would work on the new product if you got fired if it didn't hit $100 million its first year.
One thing I saw that was very, and I don't know how to bring to startups in my big company experience, was it's liberating to some extent to let people fail, up to a point. It's liberating. Because the cost of failure in a startup is so high. It's just so high. I know that's not what the exact question, and ask me in a year, but my advice is, just be careful that you don't weaponize functions.

LennyI probably should have clarified. I think this is mostly true in PLG companies where most of the growth is coming from product, but I imagine the advice is still the same, as be careful putting too much pressure on the product team to focus on revenue.

Jason LemkinWell, that's how you get dark stuff. Back in the day, I remember my sister worked at Vistaprint for online business cards, and her entire job was to force people to buy upsell of additional products on the checkout page they didn't want to buy. That was her whole job. And she was paid a large variable comp to get people to buy third party products without realizing in their checkout, and it worked. That's all she did for three years was figure out dark stuff, I mean, darkish, grayish stuff so that when I bought my business card, I also bought GoDaddy and 11 other things that I didn't want. It works, but it doesn't create high NPS, does it?

LennyMm-hmm. No.

Jason LemkinThe thing is, here's the thing that you have to think about. What's crazy, Lenny, now, and I talk to a lot of these folks is, there's so many SaaS companies that are a billion or more in revenue. I just wrote up, there's just Pimcore, which is SaaS for . I just wrote up, it just crossed a billion in revenue. So many folks are at a billion. CloudFlare just crossed a billion. And the only way you can do that is if your revenue compounds.

And in fact, just myself, I just interviewed Matt Mullen from WordPress, 20 years he's been doing this, and he said the number one thing he didn't understand at WordPress, at Automatic, was the power of compounding. When you do these things that are customer hostile, and a lot of us were under stress this last 12 days, to hit the numbers, right? This is your job as founders, is you got to load balance the fact that the cash has to last and my investors are mad with me, but nothing matters in B2B that it compounds. And some of this dark stuff you're talking about on PLG, it anti-compounds, right?
And I would say, let me flip it around. The magical thing at the high level that it compounds, if you have a self-service model, a PLG model, I actually think the number one most important metric is churn. It's going to this churn, churn, churn, churn. And when I meet any startup for investing or anything, if the churn is not top decile for a low end product, I'm always out. It's almost unsolvable. It's almost unsolvable. This 3% to 4% a month churn rate that a lot of SMB stuff, it's almost unsolvable. I think that's where the energy should go, is relentlessly bringing down churn so that, 20 years from now, we all have billion dollar AR companies. That's what we want.

LennyI have a rapid fire set of questions before, actually, the lightning round. We'll see if we have time for all these things. I just have a bunch of random questions that I'm going to fire at you and and see what comes up. Sounds good? Okay, cool. I got a thumbs up. Let's do it. Okay.

What is just one thing a founder or product leader can do to become better at sales?

Jason LemkinThe number one thing they can do, and this is very tactical, at the end of each meeting, because again, both of them are good middlers, the head of product and the founders are good demos, they're good at talking shop, they're good at talking in the industry, they're good at talking workflows. Learn. This is the only school you have to learn. Even if you're not comfortable asking for money, learn to ask for what's the next step, Lenny. This is what all great salespeople have learned to do. Actually, mediocre salespeople are terrible at this. The best salespeople never leave a meeting without a next step. The next step does not have to be a check. Don't break the relationship, but what's the next meeting? The next meeting might be, "Lenny, is there someone else at your company that I could do a demo for?" People are lazy, they don't want to do multiple demos.

But in 2024, we all have to demo multiple stakeholders. In 2021, it was one stakeholder. Now, it's a four-stakeholder sale. If you don't know what to ask at the end of the call, ask, "Who else? Lenny, is there someone else? I know you're excited to buy our product, but who else? Is there someone else in the organization? Can I help you? Can I just do a demo?" A demo is not threatening. Whatever the next step is, "What's the next step we can get on our books?" And listen. The best salespeople march deals step by step by step by step. And then, they put in the time. They've done the demos, they've done the pilot if they need to, they've helped them get going, they've helped them see the value. And then, if it takes six steps to say, "Okay, Lenny, now, we've got five folks at the organization using it. They've seen, here's the deal. They love it. What can we do, Lenny, to get going? Can we get a contract signed so we can get going on February 1st?" It's just very natural.
And founders just end the Zoom. They end the zoom, and they wait. They wait in their inbox for the next step to come, but it doesn't, it rarely comes on its own. That's the number one tip is, make sure yourself and you log it in your CRM that you always have a next step after. You don't have to be great at sales. As long as you're moving the ball down the field, then, get it into the red zone, and then, figure out how to ask for the money. But you don't have to ask for the money until it's in the red zone.

LennyAmazing. While we're on this topic, is there a book or a course or anything that you'd just recommend folks go to get better at sales? Just, is there some tactical, "Go read this thing, it'll help you?" Or is it just, it's hard, you're not going to figure it out reading a book?

Jason LemkinI am a voracious reader. If I only wanted to plug myself, and I usually wouldn't, two things that we have, we have something called SaaStr.University. SaaStr dot University. It's free. There's a pretty good course on learning about sales. It's not perfect, but it's pretty good. It just organizes a lot of the stuff we're talking about and it's free. I think it's pretty helpful. We actually wrote a book called From Impossible To Inevitable that sold about 100,000 copies.

LennyOh, wow.

Jason LemkinI did almost none of the work, although a lot of is my content. Aaron Ross did it. It's actually really good, and it interviews a lot of top sales leaders and goes through a lot of stuff we did. I don't usually hype it, but for 15 bucks, I think this ... And actually, I've never made one dollar. I've never even gotten a check for these 100,000 copies, but I do think it's actually ... The second edition's pretty good. I think, if you like what we're talking about, the SaaS University and the others. I just hyped my own course, which is free. I don't think I'm selling something if it's free. The book, I don't make a dollar on. I'd be very cautious, and this is tough, maybe this is something we can work on together. There's so many courses and so many people selling stuff the last two years. Just be cautious. Just be cautious.

The last thing I will say is, there is another community called Pavilion, and I do think it's great, Pavilion. It does have a lot of networking and stuff for sales and connecting sales with founders, and I am a super fan of what they're doing. That one's worth investing. But be careful about Bob and John's sales courses on the internet. There's too many.

LennyAwesome. All right. We'll link to all those things in the show notes.

Next question, what is the ideal trial length for a free trial for sales team? Is it 14 days, a month, years? What do you recommend?

Jason LemkinTomas Tsangaris did a whole SaaStr presentation just on free trials and free trial legs. It was really good, but the one thing you didn't know, which I know just being an old timer is, one of the reasons we have 14-day trials on the internet is, in the old days, the Salesforce sales team, when they were SMB focused, wanted to close deals that month, so they forced Salesforce to move from 30 to 14 days. There was no evidence it was better for the customer. There was no evidence that it got usage going or people ... They just wanted to close deals the same month.

That's something to be cautious about, these metrics. And be cautious, since we're talking to product folks, be cautious that they're customer centric. Salesforce is very enterprise now, but in the old days, it pushed it to 14 days so the sales reps could close deals faster. What we learned from Slack and Zoom until recently was infinite trials work pretty good. So does Canva. Slack and Canva, and until recently, Zoom, were okay waiting four years to convert. And those are epic companies. Those are epic companies.
And these are one of the things that only founders can make these decisions. I wrote this post years ago saying, "Who's your VP of Free?" Because who's got a VP of Free? Do you know anybody that has a VP of Free? I got a VP of Growth, I got a VP of Product, but if you have this massive free base, who's your VP of Free? I know almost no one that has a VP of Free. And usually, it's some kind of collaboration between product and the CEO. They're the VP of Free, but even then, you need a VP of Free, and we don't have one. There's no perfect answers, but in a world where we're tightening nooses everywhere on trials, we're tightening nooses everywhere, be careful the advice you get, be careful the short-term advice.
For example, another related terrible piece of advice VCs give you is switch to annual contracts. This is terrible advice. Terrible advice, Lenny. Terrible advice from people who've never built products and aren't in the field. Going to annual contracts, on a spreadsheet, looks great. On a spreadsheet-

Jason LemkinGoing to annual contracts on a spreadsheet looks great. On a spreadsheet, it looks great. You know what's better? Letting customers pay what they want to pay. If it's you or me buying for ourselves, Lenny, we're still going to put it on a credit card, aren't we? If it's our own personal... And we want to pay monthly, usually, we don't know. We usually want to just try it monthly. Big companies want to pay annually because they have procurement departments. Why force people to go the way they don't want to go? So, just start, this is a product audience. Product needs to be the voice of the customer. It's not so much customer success as it used to be. It's not so much sales. You've got to be the voice of the customer together with the founders and push these things.

Think about, I would do the longest possible trial that is still customer-centric and understand there's tension. Understand there's tension, right? I say anytime I'm in a board meeting where some VC says, "Let's do annual for an SMB." I mean, I'm like, "No. Show me the money. Show me the evidence that this is better for the customer." Right? How many times have you gone to buy something for yourself and it's 19 bucks a month? And that's annoying because it's an credit card charge. But do you want to pay 240 up front? I mean, maybe you do it for a Riverside or something you use all the time, but some random product you just discovered, you're just going to bounce.

LennyYeah.

Jason LemkinSo, who's going to show the data in the bounce, right? A related point for like in sales. No one does enough. Everyone does these win-loss meetings, but no one talks enough about the deals they lost. Everyone talks about the deals they won. All the lore, the tribal lore in sales is how we won the deal. People should be spending more time talking about deals they lost than the deals they won, right? And same thing for this PLG motion. If you make your... Yes, I give everyone a pass for 2023, everyone whose growth plummeted and did things they shouldn't. Did price increases they didn't earn, cut the free trials, hid their free editions. I'm going to give you, look, you've got to give your team a little stress relief, right? So, I'm giving every person I work with, every portfolio, everyone a one-year pass, but the past is in the past. We got to get back to being customer-centric and building businesses that build to 1 billion ARR on their own because they're wonderful businesses that are product-centric, right? That recur. And every time you rip a customer off, you lose, the relationship's damaged, isn't it?

And a controversial thing I say to the product team, but I think this is the right thing if you're going long, is look, everyone raised prices last year, as you know, right? Everyone raised prices. The question I ask folks is, "Did you earn it?" What feature did you ? If you raised prices 8% last year, did you add 30% more value to your product? In the old days pre these crazy years, the answer usually was yes. People would wait up, they would wait a couple years, right? And the whatever product from four years ago was so much better. It really was. Really had earned 1995 instead of... Last year, no one earned their price increases. No one came out with an amazing new edition, an amazing new functionality that earned it. They just sent you an email saying, "You're paying more." So we get one pass, but earn it. Earn your price increase.

LennyAlmost 600,000.

Jason LemkinOkay. 600,000. Now, not all of them convert, do they?

LennyNo, no. That's exactly how I look at it. It's kind of this Brian Belfort is this... Yeah.

Jason LemkinWhat about the 590,000 of them that love Lenny that don't convert, right?

LennyYeah.

Jason LemkinIf you over monetize them, then Lenny's community doesn't exist if you over monetize them. But when you bring in a VP of sales for Lenny and a VP of growth and... You can't expect them to care as much about that long tail as you, right?

LennyI love your passion around this. So, what I'm hearing partly is you're a big fan of freemium, essentially, right? And the benefits of product-led growth where there's something you could just use indefinitely, or do you still think that's a trial where it needs to end at some point? Or is it just like, "No, freemium is great in a lot of cases."

Jason LemkinListen, I'm a big fan of long tails when they work. They don't always work for enterprise products. I'm a big fan of delivering more value than you take out for your customers. And I am a big fan overall of free, because, and I know you'll agree with me this, every founder figures this out at some point, free products are better software. Products that cannot offer a free edition cut corners because they don't have to be good at onboarding. The products that do not have a free edition have human beings that bridge the gap between buying and deployment. And that's okay at ServiceNow, and that's okay in certain products, but the best products invest the engineering cycles to have a free edition. Whether that's truly free, whether it's an extended free trial, whether it's a long tail or a medium tail, the amount of... All of your product is better if people can actually, if you have a free edition, all your customers benefit, even your enterprise customers benefit, they all benefit.

LennyThis idea of VP of free, I think technically it's probably the head of growth for a PLG company or the person leading the self-serve part of the business.

Jason LemkinBut even in the organizations I work with that have those structures, that person is focused on monetizing that tail. Who stands up for the 590,000 other readers of Lenny? Who's their champion?
Yeah.

LennySo, yeah.
Makes sense. Oh man, there's so many things I can go into and want to go into. I also want to let you go. So with that, is there anything else, Jason, that you wanted to share before we get to our very exciting lightning round? Anything you want to leave listeners with?

Jason LemkinI think just make this the year of the customer guys. And I really think that sales has been under so much pressure the last 18 months. Customer success has changed. Product teams have to step up. This is your time to do great things this year as product people. Be the voice of the customer. Be the VP of free, be the whatever. Be the champion. Stick your neck out. Work harder, folks. Work harder. The funnest part of anything in startups is working hard, but in product it's extra fun. By working harder, you have the more fun conversations. Find the delight in... The delight in product is making customers happy. It's not worth it otherwise. Otherwise, it's drudgery and it's endless PRDs and Gantt charts and mindless discussions. Make your customers happier this year, you will be happy. This is the year of product and we all get a pass for whatever bad deeds we did or mediocre deeds we did in 2023, get back and be the vanguard in your companies.

Startups need, and bigger companies, they need someone to inject energy again, in many cases. Energy has been lost. And it would be great if product can do it and say, "Listen, let's do something, even if we're not exactly sure how to get more leads, okay? Even if we're not exactly sure what to do, there's one thing under our control is the code we write and the product we ship. Let's do three great things this year. Let's just do them not good, great. Let's do three great." And what you'll find is the whole company will respond, including sales, including marketing, including... If we start shipping great thing. Few things inspire teams more than when you're shipping great products. So, be... If you weren't the leaders the last two years, if you were being forced to weaponize your customer base somehow ship three great things this year. That's my challenge. Ship three great things.

LennyI love this. This is the year of product, that might be the title of this podcast.

Jason LemkinYes.

LennyJason, we've reached our very exciting lightning round. I've got six questions for you. Are you ready?

Jason LemkinOkay. I'm worried about the first one, but go for it.

LennyThey're very non-surprising, because they're always the same. What are two or three books you've recommended most to other people?

Jason LemkinThat's the one I just want to take a pass on. I know they're the same. I read more than anybody else in the planet, but I wish I had those two great, great books that have changed my mind in the last 12 months, but hopefully I've added some value. But this one, I think I got to take a mulligan on it perfect answer.

LennyAcceptable answer. Is there a favorite movie or TV show that you really enjoy?

Jason LemkinOh, the Terminal List.

LennyThe Terminal List?

Jason LemkinThe Terminal List, yeah. I'm not into the Chris Pratt. I'm not into that goofy superhero movies he does, and I know people like it, but The Terminal List, it's pretty, it's I got it, it's written by this ex Navy SEAL that I think tech people don't read the... Everyone, but outside of tech reads this author, but Amazon did this thing with The Terminal List and I think the reason it gripped me, it's like this post, it's like a lot of tech is right now is we're trying to do the right things, but are we doing the right things? It's just confusing. So this one, I couldn't put down, The Terminal List. That was my favorite show. The other one, the one I liked that I couldn't believe. You want the second one? Even though as product people, Maverick, and I'll tell you why. This movie Maverick, okay, you wouldn't think I'd be a Maverick guy, but the quality of this product, it was so high.

And what's interesting, you remember Maverick was supposed to come out before COVID, right? And Tom Cruise said no. He's like, "This is such a good product, we're going to wait years for this thing to come out." I'm like, " I'm not going to like this. I mean, cocktail was pretty good, but I'm not going to..." But as a product, when... I've watched this movie three times from a product perspective and just like software, when something is done that well, no wasted calories, no... You see everything tied together. That's the kind of software we love, right? It just delights us when it works better than we expected. So, those are my two.

LennyYou also did all his own stunts, which I think is a good metaphor for the VP of product, maybe being involved in sales?

Jason LemkinActually do the work.

LennyYeah, exactly. Oh man, I'm stretching it. Okay, next question. You answered a few of these already, but do you have a favorite interview question that you like to ask when you're interviewing salespeople, especially?

Jason LemkinI answered it, but I'll bring it up again in case you do it again, is, "What do you want to do your first 14 days to head of product or head of sales? What do you want to do your first 14 days?" It's not a technical 30-day plan, you don't have to do 28 slides. It's what I call a Colombo question. Not that I really watch Colombo, but Colombo is this old detective on TV who, I don't know if you ever, he would ask these dumb questions, right? And then the murderer would thought Colombo was so dumb, but by the end of the episode he'd always incriminate himself because the question. So, when I interview, I always do Colombo questions. They're never tough ones, right? They're always nice. I don't know if I'm nice, I'm honest, but the interview . But Lenny, what would you do your first 14 days as VP of product here? And they don't want to visit customers. Don't hire them for either all sales or product. Just don't hire them.

LennyI've got the answer now. That's exactly what I was going to say. Next question, what is a favorite product that you have recently discovered that you really like?

Jason LemkinMy two aren't really amazing, but I'll answer them. I love this Opus Clip app for making clips from video. I know you have a whole team, so you probably don't need it, but I produce a lot. I mean, a lot of us do content marketing, right? Whoever does it. I produce a lot of content. I don't have enough time to do this. So, the only AI tool that I've found helpful so far is Opus Clip, which takes all of the incredible amount of YouTube content we have, force ranks it and turns it into 59 second clips. And I'm a case study on the website, I tried the earlier products. They were almost there, right? But it's not, is it as good as a clip team? Right? Is it? No.

But literally in 60 seconds, what's interesting is it can do something, I don't have time to, I could never make YouTube clips. I could never make Instagram shorts. I could never make... It just would never happen, right? It would never happen. And the fact that one product enables you to do something at a minimum viable quality you couldn't do before, I'm a super fan. It's pretty interesting. So, that's my favorite. And my other one is this one. This is the folding phone that's finally as good as a normal phone. See, there's The Terminal List that I've got folded up and it just works.

LennyThat's wild. .

Jason LemkinWeighs the same as an iPhone.

LennyWow.

Jason LemkinAnd so the reason it's cool is this has changed the way I do productivity. One Plus, it's the One Plus. One Plus, yeah, it's the first one that's the same form factor, same weight, same... So there's really no, there's no loss, right? And I can use my normal phone here like I'm using, it's a little funky, but it's the same... And then to be able to do content, to be able to check, to be able to do full email, full account, full everything like an iPad.

LennyWe see your Tesla where it's going, that gets parked. That's very cool. So, it's basically like an iPad plus a phone in one.

Jason LemkinYeah, I probably use this 50% of the time of the iPad.

LennyWow.

Jason LemkinSo, that's it. That is it. The other ones that-

LennyAnd that's an Android?

Jason Lemkin... Make sense to me. Yeah, it's a Android, yeah.

LennyAmazing. I had not seen that. That is extremely cool.

Jason LemkinVery cool.

LennyTwo more questions. Do you have a favorite life motto that you often come back to share with friends or family, find useful in work or in life?

Jason LemkinIt's, "Be kind." When I reflect on my career, right? Mistakes, I don't think I'm mean. I actually think I care more than most people on the planet. I like to think I've helped a lot of people, but it's not taking the time to be kind at times and not taking time to be kind when things don't work out. Not taking time to be kind when you leave a situation. Not taking time to be kind when maybe someone's done the wrong thing, right? Not taking time to be kind to a customer that leaves, right? I remember in the early days of Adobe Sign of EchoSign, we had a top tech customer, and I killed myself to close this customer, right? Famous, huge, huge tech company today. And then our champion changed, right? Champion changed is the big issue in software and product and came in and brought in DocuSign instead of us.

And man, I was just so mad. I just tore into this guy. This guy had actually had dinner at my house, right? And he actually never, he just did it because it was good for his own career, right? And I was so mad, but I broke the relationship forever, right? That's just one random example. And I just think there's so much advice to fire fast and to be relentless and do all these things, right? But you've interviewed so many people, Lenny, right? I mean so many great leaders. I haven't done what you've done, but I've talked to almost all the top CEOs in SaaS, okay? And they're kind. It doesn't mean that they're soft, they're not soft, okay? They make tough decisions every day, but they're kind. And so in this world where everyone feels like they're getting ripped off or they're not paid enough, or I want founder pay for founder work, this motto, really it's troubling.
Everyone is founder pay for founder... "You want me to work more than 30 hours, Lenny? I need 30% of the company. I need founder pay for founder work." It's like, I hear you. But you'll find that by being totally committed, going to 110% and also finding a way to be kind, that will endure across your whole career. So, I know it's... Because I think I'm good, but not always kind. It's how I challenge myself all the time. Be kinder in that conversation. And the big epiphany, we already talked about it, it shouldn't have taken me this long to realize that anytime an employee fails, it's your fault, be kind. You hired them. They never knew what they were getting themselves into. If the job's too hard, if they lack the skills, if there's not enough budget, if there's not enough people, if it requires too many hours to work, you should have known that. Not them. Be kind. Be kind to every single person on your team that doesn't work out. That's not just putting together an email spreadsheet and sending it out. Try, try harder. Be there for them. Be kind.

LennyBe kind. I love this. I know that you actually, your username on Twitter includes, "Be kind." In your actual-

Jason LemkinIt's a reminder.

LennyYeah.

Jason LemkinIt's a reminder.

LennySo, you really back this up. Amazing. Okay, final question. You're on a giant conference, SaaStr.

Jason LemkinYes.

LennyFirst of all, just talk about what it is so people know and explore it and check it out. But the actual question is what would surprise people most about running a conference like this? Things that they know, think about it goes into running a conference like this.

Jason LemkinAny business, no matter how weird it is, that's at scale, the best one in it, it's always interesting, I think for case studies, right? The best, pick anything, the best cup maker, whoever it is, whoever makes the best... This is not an interesting business, the Starbucks cup on its own, but the best person, I pretty much guarantee you there's a good story there, right? SaaStr is a community as well like you have. We started this really early in 2011, 2012 for B2B founders back when that seemed like a weird thing to do. Now it doesn't seem so weird. So, we built a lot of content and we started doing events and meetups. I never did a meetup. You do a lot of meetups, but when I did meetups, I'd never actually even been to one. So, I did meetups in 2012 and 2013, but 1,000 people came to the meetups.

That will make sense to you today, but a decade ago for B2B, it was pretty, people were like, "Why are all these people here? We thought there was six of us that cared about B2B." So, then we did a big event. We did a one-day SaaStr annual in 2015, and 3000 people came including the evening. And so we just kept going. So, we get about 10 to 12,000 people together a year. What that means is change. It's no longer novel. I'm not the only person producing B2B content anymore. I'm not the only founder that sold their company like in the old days. There's plenty much more successful founders and better, I certainly, I don't do very many podcasts, because I'm not a hundredth as good as you. I do one a quarter, for example.
But the events have become this meeting place for founders that have hit scale, that are somewhere between 1 million and 20 million. And especially folks that aren't in Silicon Valley, especially folks that aren't sitting in Hayes Valley or wherever, that don't have a community. And that surprised me in the beginning how many international folks would fly all the way to the Bay Area. I remember this founder came from Perth, Australia for the first afternoon. I'm like, "Thanks for coming, but this is a lot of work." He is like, "I didn't come for you. I came because there's no one like me in Perth." So, it's taken on a life of its own. There's a lot of learnings. I think, I didn't intend to do mass scale events. I intended to just do meetups, because I had a community like you do meetups. So, it was absolutely an accident. The learnings are, it's extremely expensive and it has this weird curve. Okay, that's this weird curve where, and this is more because I think actually all founders, all startups should be doing events for their own customers, at least steak dinners I've written about. You should get your customers, if you get your customers and prospects together, you sell more. Get your customers and... It does not need to be a million dollar or 10 million event. It can be Roots Chrises, it can be whatever. It does not even need to be fancy. Just get them together.

LennyIt has to be steak though.

Jason LemkinYeah, well, no, but steak does work. I mean, I'm not a big steak guy. It could be any, just something nice where they want to go. It, just where they want to go. Your customers will sell your prospects for you. Your customers will do the selling for you bring them together.

When you do it really small, it's cheap, because how much does that back room cost at the steakhouse, right? It's worth it if you get one big deal out of it, right? And then you graduate and then you'll do a meetup and you'll do it at someone's office. Some tech company, they'll give it to you for free, they have an extra office. That costs nothing, right? And then you're like, "Well, that went well. We got 100, 200 people came to Lenny's thing at Digital Ocean." And then you say, "I'm gonna do an event." And then you rent a theater, a disuse. And these theaters are actually kind of cheap because they're dark during the day. There's not a lot going on and a lot of... Not movie theaters but music. So, those are cheap. But then you're like, "Well, there's only one stage and it smells like beer."
So, then the next year you do a hotel and a hotel's pretty expensive. It's like half a million, 800,000 and I hated hotels. But you know what I learned from the business model? It's turnkey landing. So, your marketing manager can call up the Hilton in any city and in two weeks spool up some mediocre AV, some mediocre chicken wings and drinks, okay? And you and I don't like to go to the Hilton that much. The ballroom C, we don't like to go to events , but it turns out your customers don't care. They want to be together and talk about your app, right? And then if you do community like you do, you could probably charge a couple $100 for tickets and get some sponsors and bring in some revenue, right? But then after Hilton Ballroom B, it costs $2 million to turn the lights on.
And SaaStr annual... So, our Europa event in London's in early June, June fourth to fifth, please come if you want. That costs $2 million to turn the lights on in London. To turn the lights on in the Bay Area for 12,000 people in September in the Bay Area, which is the most expensive place, right? It's $10 million to turn the lights on.

LennyHoly shit.

Jason LemkinIt's $10 million to turn the lights on. Now, I'm being a little expansive in what I mean by turn the lights on, but this is what it's going to cost you. It's going to cost you about $1000 per attendee in the Bay Area or Las Vegas to have a mass scale event. Not smaller, not one day in Grand Ballroom B, but a multi-day event, right? The AV is 1.5 million. The food and beverage is 1.5 million. The tenting is $800,000. I can keep going. So, once you get to 20, 30, 40 million in revenue, quietly, there's public companies out there.

They have software like Margins at that scale, but before that, it's brutal, right? And when I started doing these events, I interviewed the head of it back before March 2020 when tech companies did their own events, they've pretty much given up, which is an interesting side topic. Big ones like big, not small ones, but big ones. Biden View, the head of events at everyone, right? At Twilio and Marketo and dah, dah. They all be like, "Well, how'd the event go?" It'd all be the same. Well, we brought in about 1.5 million revenue. " Oh, okay." "And we lost 2 million." Everyone lost 2 million. Every single one lost 2 million. And you could see in the financial state, even Zoom at that scale just announced how much money they lose at Zoomtopia. So, it's a terrible business. What I like to say is it has diseconomies of scale. The Lenny's little free meetup costs zero, right? And then the one at Cloudflare's office costs zero.
And the one at Hilton B maybe costs $200, but then it costs $1000 per person at scale, right? Even more like Moscone like in San Francisco is probably the most expensive. You're approaching $2,000 per person, because you have to buy about 15 to 20 million of hotel nights to do an event in Moscone, right? So I don't know if that's... We could, I mean it's a side topic, Lenny's side podcast for people that care. But this diseconomies of scale. But there are a handful of public companies that do Lions, Money 2020, Shoptalk, a few others that are at SaaStr scale. And they cobbled together these very profitable public companies. But they all got to do at least 20 to 30 million, because you've got to get over a 10. And it's intimidating to get over a $10 million net, right?
And so what it means is we have to spend 14 to 16 months each year planning for SaaStr annual because it's not that fun if you fall six or $8 million behind. That's what happened in March 2020. We were the first major event to be canceled by COVID in March 2020. The first one, RSA happened for security the week before then we got canceled. So, we lost $10 million in one day and it took a long time to dig out of that hole, Lenny, especially since we monetize nothing, it took a long time, but they're worth it.
I know you don't do traditional events, but you do do meetups in your community, and I know they're worth it. I know they're worth it. Bringing your customers together, bringing your community together, and we talked about this offline before we started. Second tier, third tier events I do not think are worth it because they do not attract the best people. It's just a fact. Most people, it turns out from our founders are our core ICP. They go to two events a year on average, two events a year, okay? And they'll do other steak dinners. So, if you go to one of the two that they're at, you just might bump into Jeff Lawson or Eric Juan or whoever the next one. They might be there. That might be one of their two, but they don't go to number three through 10. They don't go to these. So, my role in general is people wonder, should I go to events? Is it worth my time? It's a waste of time.
And I know you've thought about it. And the irony is, even though we produce events, I used to think that. I didn't want to do events, I just wanted to do meetups, right? I was shy, I just wanted to do meetups. But then I learned over time that the best events bring the best vendors, the best executives, the best everything together. So, pick the one or two best events in your industry. And even if you're antisocial, try to go to one or two a year, go along. It pays off. It pays off, but maybe don't bother with the rest, even if they're ski slopes or they're fun that the subscale, subscale just doesn't work for meeting and marketing to people. It just doesn't work.

LennyI said at the top of this podcast that there's a billion things that we could talk about, and I think that's exactly what happened. We can go in so many directions. And that alone was extremely interesting, because people want me to run a conference and I really don't. And I really enjoy the meetups that we have now. And we actually do have sponsors that cover drinks and food and things like that, and they're very chill, and I really love what happens at those things. But yes, this is really good information. Jason, I have two more questions for you that I ask everyone. I think we went through a couple of these things, but just real quick, where can folks find you if they want to reach out and maybe follow up on some of the stuff you talked about? And how can listeners be useful to you?

Jason LemkinIn general just go to this kooky, URL, SaaStr, saastr.com. That's a way to access a lot of what we're talking about. If they want to reach me to be transparent, I get a lot of impound, like I'm sure you do, to be honest, guys, it is hard to process the amount of inbound that folks get, right? But I'll give you an insider tip. I do see almost all of it. So, if you want to reach me, if you just want an hour of my time randomly, I'm sorry, honestly, I'm sorry, I don't have that hour of time, okay? But if you want to interact lightly, I mean, I'm on Twitter all most days @Jasonlk. I'm on LinkedIn a lot, just search for me, Jason Lemkin. LinkedIn's pretty cool. I have 260,000 followers. We have really good conversations. And I will tell you, if you have a question like you really need some help in your business or you want to do a pitch, if you send me the world's best email pitch, I will read a 100% of them.

Track it, put it in Mixmax, put it in HubSpot, put it... You'll see I'll open that email if the title's good. It doesn't mean I can respond. I'm sorry, no, Lenny can't respond, but realize it is going to be read. If you need a favor, like a help, if you ask the question super discreetly like, "Jason, here's the LinkedIn, I'm Lenny. I'm trying to hire this person. I'm at four millionaire doubling. Should I hire her?" There's a chance I'll look at that LinkedIn, I can tell you, or if it's one question, but if it's an hour or coffee, it isn't going to work, but it is going to get read. So, do that by email. Do it even by LinkedIn. I didn't used to read those LinkedIn emails, but if it's really good, I will read it and I probably respond to five or six of them a day.
I give to the extent that it's helpful, free answers, free advice. Not that I charge for anything, but make it good. Don't ask for coffee. So, many folks have written this, the most important people in the world read email. It's an open medium, right? And a subset of those folks actually read their social media. Even Elon Musk reads his, before he bought Twitter, he read it. You can access almost anyone in this industry. Just be super strategic about how you do it. Again, put yourself in your shoes. Would you answer this? Would you do this? But I would say half the stuff gets open to read. So, I know that's a rambly answer, but first, we talked about sales. You can reach anybody in the world via email. It's magical.

LennyI'm sorry for the many emails you might get from this podcast. That is actually really good advice. Resonates deeply with me as well. Jason, thank you so much for being here.

Jason LemkinThank you for all the time, Lenny. I'm a super fan. It's great to be here and let me know anything I can do to support you or your community going forward.

LennyI really appreciate that. And the same in reverse. Bye everyone. Thank you so much for listening. If you found this valuable, you can subscribe to the show on Apple Podcasts, Spotify, or your favorite podcast app. Also, please consider giving us a rating or leaving a review as that really helps other listeners find the podcast. You can find all past episodes or learn more about the show at Lenny's podcast.com. See you in the next episode.

Jason LemkinHere's the mistake that 99% of founders and sales reps make. We're not really selling in B2B, we're solving problems. Our job as sales reps in SaaS is to not sell a used car, okay? We are selling a Tesla Model 3 performance. It has competition, I might not need it this week, but it's pretty darn good. Let me help you get you into that Model 3 performance today. I've even got a special discount for the end of this month, and let me just help you. I've spent four calls answering all your questions and I've explained to you all the things and why the supercharging network is better than the regular one that doesn't really work at the charger near your house. I've gone on Google and I've seen there's no charging network near your house. There's only Superchargers. I got you, don't I? That's the job of SaaS and sales because we're not selling commodities.

LennyToday, my guest is Jason Lemkin. Jason created and runs Saastr, the world's largest community for SaaS and B2B founders. He also runs two of the biggest town conferences every year, one in the Bay Area, which attracts over 15,000 people, and one in Europe with over 3,000 SaaS executives, founders, and entrepreneurs. Before Saastr, Jason was the CEO and co-founder of EchoSign, which he grew to over 100 million ARR and then sold to Adobe where he ended up as a vice president of their web services business. If you follow Jason on Twitter or LinkedIn, you know how much wisdom he has to share about all aspects of building a successful SaaS business.

In our conversation, we focus on what I find most product leaders have the least experience in, building a sales team. We get very practical and tactical on how long you should wait to hire your first salesperson, what your one to two first hire should look like, why you should actually hire two salespeople, not just one initially, how to comp them, how to interview them, when it's time to hire a VP of sales, how to avoid your salespeople flaming out and burning through all your cash. We also get into how to make the product and sales relationship healthier, including how to push back on sales and feature requests, why your head of product should be super involved in your sales process, how long you should make your trials, why you should avoid annual contracts, and so much more.
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Over 5,000 fast-growing companies use Vanta to automate up to 90% of the work involved with SOC 2 and these other frameworks. For a limited time Lenny's podcast listeners get $1,000 off Vanta. Go to vanta.com/lenny. That's V-A-N-T-A dot com slash Lenny to learn more and to claim your discounts. Get started today. Jason, thank you so much for being here. Welcome to the podcast.

Jason LemkinHey, I'm so excited. Long time. What's the expression? Long time fan, first time dialer or something?

LennyCaller?

Jason LemkinFirst time caller, yeah, first time caller.

LennyFirst time guest.

Jason LemkinI don't know if that exists in 2024 or not, but yeah, that's me. So thank you so much for letting me come.

LennyIt's absolutely my pleasure. I feel like you're the kind of guy that I knew would be on this podcast eventually, and I'm glad that we're finally doing this. I also feel like we can go in so many directions. I feel like you have so many insights on so many parts of building a business, especially a B2B business, but I thought it would be most interesting to dive deep into building your sales team, essentially trying to help people figure out how to start their sales team, scale their sales team, and all the elements they go into it. How does that sound?

Jason LemkinI think it's great. I think it's an evergreen topic, but I think there's remains a consistent set of confusion, fears around how to build a sales team, and it's evergreen. The tools change and the pace has changed, but the issues, I love to dig into them because we keep making the same mistakes as founders and executives again and again and again.

Lenny100% agree. It's such a black box to me. Sales, I've never done sales, and I'm always just like, "I have no idea what's going on here." So this is how I learned from folks like you. You touched on this now. Now, I wasn't going to get on this, but I think it'd be interesting just this question of, does everyone need a sales team? Will you need a sales team if you're listening as a founder? Is it simply, if you're a B2B business, you'll need a sales team? How should people think about, "Will I need a sales team?"

Jason LemkinIf you truly build a self-serve product, you can either never have a sales team or Slack defer it or Canva really defer it. Canva didn't really build a sales team until they were well north of 500 million in revenue because it's epic self-serve. Slack started all self-serve, and by the time they went public, the majority of their revenue was enterprise sales. So you can sequence things. You can have hybrid models like a third of Asana's revenue is still from self-serve, and two-thirds are from a self-serve motion. So there's all different hybrid things.

The most important thing though I've found is however you get those first 10, 15, 20 customers, be honest, be honest, and if you've talked to them as a founder and you know that they need a sales type motion, they need effort to deploy it, they have questions about security, they have questions about competition, they have onboarding requirements, and you say, "Hey, I don't like sales, so I'm going to do a PLG motion," you'll fail.
One of the things that I've done with so many founders over the years, and it shocks them at first, is your first 10, 15, 50 unaffiliated customers, the ones that find you from the ether, they're the next 50, 100, 200, 1,000, and you can either embrace them or run for them. Too many producty founders find that, "Hey, gosh, I'm going to have to do sales," and they exit it. They exit it.
I'll tell you a company I invested in 18 months ago when things were easier, maybe 20 months ago, they were doing 5 million in revenue, growing over 100% with the sales like motion. Things got harder, things got harder as they did for many of us, and they decided to fire the whole sales team, and now they're doing less than one from 5 million with beloved customers. If I told you the logos, your jaw would drop. Over 5,000 20 months ago to 1 million today because they fired the sales team because the founders didn't like sales, they thought it was icky, they didn't want to do it, they were tired of doing it. I can tell you several stories like this.
So you've got to be honest about the ... Sometimes we get it just right on day zero. Sometimes we know exactly how our company is going to work or Lenny's podcast is going to work. We can predict the future perfectly, but I find in B2B, a lot of times the industry, we end up winning. The segment of the industry, the type of customer is not what we initially thought and either lean into it and be a success or run from it because sales is icky and risk failure.

LennyWhen you talk about being honest, what you need to be honest about is that you need sales help to close customers?

Jason LemkinBe honest about that. Just be honest about, yes, the motion that it will take to get those first 10, 15, 20 customers, and if they were able to find you by putting their credit card and no one had to talk to them, then that's your DNA today. It doesn't mean you won't go up market later like a Slack or a Canva, but if you can get them all to do that and you never have to talk to them, then get really good at viral loops, get really good at almost B2C type motions, get really good at this kind of stuff and hire growth hackers and do the whole almost B2C-ish motion, which we have at self-serve, but if your first 10 customers come in and say, "You know what, Lenny, I'll pay you $5,000, but you've got to solve this problem I have with online video," that is not a self-serve motion. It is not a self-serve motion.

Even worse, sometimes worse is your first 10 customers, five of them sign up online, but it takes a huge amount of effort for 19 bucks a month, and then five say they'll pay you $5,000 a month. Some founders are like, "I'm going to work on the five that pay us 20 bucks a month, not the five that'll pay us $5,000 a year." I find too many folks that don't like sales, too many folks that have not had any life experience in a sales-led environment flee from those customers, and I've never seen that lead to success. We're surprised who our niche is sometimes. We talk about nailing our niche, but sometimes we're surprised that niche that finds us.

LennyThere's a lot of startups I've invested in that start off product-led growth and quickly realized, "This just isn't working," and many of them move to, "We need to actually hire salespeople and start to go top down."

Jason LemkinMost companies are a hybrid. Even there's weird hybrids like there's folks like Mongo and Snowflake. Mongo has, well, maybe Mongo's much better example, Mongo has a free low end version, and there's open source too. It's a little confusing, and then there's not a lot in the middle, and then there's a lot of big. There's all different ways to combine a product-led or self-serve motion with sales-led. Too many founders in the beginning think it's either or. It's not either or.

LennySo I think the big takeaway here is sales is not a question of if you're going to need a sales team, it's a matter of when. The Canva example is crazy. Maybe that's the

Jason LemkinBut they still have one. But they still have one now.

LennyThey still have one. I think Notion, I think at 10 million ARRs when they hired their first salesperson.

Jason LemkinThat makes sense.

LennySo I think the question that leads to is, what is a sign that you should start to hire your first salesperson?

Jason LemkinEven if you hate sales, even if you think it's icky, even if you don't like it, as a founder you've, 95 times out of 100, you've got to find a way at least to close the first 10 customers yourself. You've got to find a way. We could dig into how to do that if you don't like sales. The hack though is that even if you don't like sales, customers love to talk to the CEO. The customers love it. Here's the other thing, as a founder, you're really good at the product in the market, hopefully even in the early days. So what's important is even if you don't know how to do outbound, even if you don't know how to send a cold email, even if you don't how to do any of this stuff, and even if you don't know how to ask for a check, even if you don't know how to open or close, almost all founders are A+ middlers, A+ middlers, A+ middlers. Before we started, you and I talked about podcasts and content, and immediately it was an A+ conversation. Maybe you don't know how to close a big sponsor, I'm just making that up, and maybe you don't know how to find one, but once you have someone in your spider web, letting the conversation, you and I just had was A+, and any founder should be there by day one, by day one, and prospects love it.

If I want to buy CRM, I don't get to talk to Yamini at HubSpot or Marc Benioff, but I get to talk to you and your CRM company. It's magical for early adopters. So bear in mind, no matter how bad you think you are as a founder, you're pretty good at the middle part of sales. So find a way to get any prospects, get really good at the middle, and then work up your courage. Work up your courage, and find how to ask for next steps and money. What would it take, Lenny? How can we get going on Riverside? What would it take? We would love to have you. What would it take to get you going next week? You've got to learn that little motion, but you don't have to learn all the stuff you think is smarmy other than how to go from middle to just ask for how we can get going.

LennyI like this term, middlers. So just to make sure I understand what that means, in the middle of the conversation, you're not great at initiating, you're not great at closing, but you could talk about it.

Jason LemkinYeah, and this is where sales reps are terrible. Most sales reps, once you go beyond the five basic questions, they can't tell you how a database works or how to eliminate hallucinations from your product or how to do payroll in Eastern Southern Guam. The sales rep, and we can talk about this, they need help. They need help from the founders in the early days. They need help from sales engineers or product people, which is my favorite place to get the help as you scale, but they need help.

The beauty to founders is they don't need help in the middle. You can be 10 times better in the middle than any sales rep at your bigger competitor. If you're running, I am just making up CRM, but if you're running a new CRM startup, you can run circles around 98% of the sales reps at Salesforce or HubSpot. They have the brand, they have the partners, they have the integrations, but they cannot answer the questions you can answer.

LennyOkay. So you close the first 10 customers. What are other signs that, "Okay. Now is really the time we need to start hiring sales"?

Jason LemkinI think as soon as you've got those 10 customers and more than 20% of your time is booked up with customers, you need leverage. You need leverage. You've got to get ... If you do it too early, if you're not spending 20% of your time in sales and 20% of your time in recruiting, you're failing as a founder. You need 20% of each, 20% in sales and 20% recruiting. Nothing else really matters at some level as a CEO, maybe not as founders, but as CEOs. Once you cross the 20%, you need leverage or your calendar will die. So you need to hire one rep and you've got to hire two because otherwise, there's no A-B test. You have to A-B test humans. You have to A-B test humans. You've got to hire two as hard as it is, and there's just one cheat code to those first two. There's one cheat code.

I talked to so many founders that screwed up their first sales hires, and they always nod when they hear it. Those first couple reps have to be people you would buy your own product from. That's it. Now we can talk about other criteria. We can talk about normalizing for deal size. We can talk about industry expertise. We can talk about all this kind of stuff, but when you go out as a first time founder and interview 30 reps, and you're going to have to interview 30, and 20 are just going to break your brain because they don't do any work and they don't do any prep and they didn't even go to your website. Then eight of the next 10 are okay, but you know it's not really going to work, but you might hire them if you get tired.
If you're lucky, one or two of them, they're like magicians. They ask the right questions, which we could talk about. Then take a pause and say, "Look, no matter how strange their background was, whatever they did, it's not the right background. It's not our same deal size. It's not our industry. They actually weren't very good at their last job. They got let go at their last job, but I would buy from Lenny. I know. I've been doing this for a year. Every day, I would buy from Lenny because Lenny just explained to me my product and my customer's problems in a way that I actually believe. Forget about what's on her LinkedIn or his LinkedIn. I would buy from Lenny."
That rep always works because you can trust them with those leads. Almost every first time founder hires someone because they worked at Twilio or CloudFlare or wherever, and they talk the talk and they can say ACV and NRR, and they can talk all these acronyms. None of which matter. None of which matter. We all get attracted to logos on our resume, but in our gut, I always ask them, "Did you know that Jason was going to ... Would you buy from Jason?" They're like, "You're right. I wouldn't have bought from Jason, but he worked at Twilio." So just wait, wait and interview 30 sales reps, however you find them through LinkedIn, through use recruiters, use contingent recruiters. It's exhausting. Do everything. Work your network and then be flexible in the beginning. We're looking for pirates and romantics in the early days. We are not looking for folks with massive sales operations teams and enablement teams. You're looking for that quirky one that's got a few extra IQ points, that for reasons that make no sense has fallen in love with your little product that is so feature poor and does nothing, but they love it, they love it, they love it.
My first rep I had this back in the day, he had gotten let go by a prior startup and he was struggling and he was living in his brother's garage at the time. This was not your number one person at Snowflake, but of all the 30, he came in and what's now Adobe sign? EchoSign. He described the whole problem. He described how we would solve the problem for our customers in the early days of this category. It was clear, whatever it took we needed him and whatever we needed to backfill the garage or whatever, this was the only one that could sell the product, and he did it for a decade. Closed our first five-figure deal, first six-figure deal, first seven-figure TCV deal. Didn't scale completely. Inside of Adobe was harder to scale inside of a 20,000 person company than it was in a six-person company, but he was still there. He still made that far to the journey, but he was the only one that I knew that I would buy my product from, not that I would buy something from, but I would buy my product from.
Leads are so precious in the early days. It's so hard to find leads. That's the problem. You hire this perfect person from Snowflake and you have three leads a month and you give him two and he doesn't close them, your company's going to die. Leads are so precious. That's what folks don't get. So wait, and I know it's painful, and I know most founders have hired this person with the right LinkedIn that they wouldn't buy their product from. Just keep interviewing. You need that quirky pyromaniac that loves your product and can sell it. They're out there.

LennyAmazing advice. Wow. There's so much there. I'm going to follow a couple threads there. In terms of the level, I know a lot of people make the mistake of going with a VP of sales pretty quickly. What's your advice? I know you talked about general attributes, but what's your advice for the level and seniority of these first two hires?

Jason LemkinTwo things, one that's evergreen and one that's maybe especially apropos for today's environment. The evergreen one, which I've talked about for over a decade, and I think folks that have been through it will see it, which is you need two sales reps hitting quota closing deals before you're ready to hire a manager for them. Almost all VPs of sales, their job is to take you from rep three to 300, to take you from three to 300, to take something that's just starting to repeat, a script that's just starting to work, leads that are just starting to come in. Then take Lenny and Jason, the two reps I have, as quirky as they are, they're crushing it.

Then I'm going to hire a more heterogeneous type of person going forward. I'm going to hire the person from Cloudfare. They can't all be like Lenny and Jason, they're pretty quirky, but at least I can learn from them. What's working? What are the objections? How do we get around that feature gap? We're one year old, we're two years old. We've got a lot of feature gaps. This integration doesn't quite work. How do we box around those issues? How do we sell our 10x feature? Because if you're a startup, your product isn't very good, your software is not very good, and you have a competitor, but you have some 10x feature that is driving people to buy you something you're doing that does not exist in the marketplace.
The really good reps get insanely good at selling that, and the folks off the street, the new VPs often doesn't even understand the 10x feature. It's too subtle. It's too subtle. Why? The fact that your product is localized in Portuguese magically means you can win these deals. I'm making up something that doesn't quite make sense. So you need two reps that are hitting quota and then you hire VP of sales. If you hire it before then, you're doing a Hail Mary. It ain't going to work. It never, ever, never, ever, ever, never, ever works. You're asking them to find product market fit to be the first rep, to be the second rep and scale it all at the same time. It's mission impossible to do all four at the same time.
So that's the biggest mistake is, Lenny, I can't get sales going at my company. I can't do it, but I raised $4 million in my C+ round. I'm going to go out and hire the VP of sales. That VP of sales will not be there in eight months. You know what else? 2 million of the four will be gone because they'll never understand the product. They will never understand. There's so many things we could talk about, but if there's one thing I could reinforce for this audience, it's that early sales team, they've got to be product gurus for your product audience. They've got to be product experts. Later as you scale, they can't be or you can't scale.
When I started, when I came out of my own startup and started interviewing other folks, I remember I would interview a lot of folks at places like GitHub back in the day. I'd be like, "Do you have a technical background? Are you an engineer? Have you ever built any software?" They're like, "No, I don't. I don't know. I don't know," and I was like, "I was curious how you could do it," but GitHub was so well-established that it's 10 questions. It's 10 questions and grab a sales engineer. It's 10 questions and grab ... So you got to be really good at 10 and then you grab a sales engineer. That doesn't work in the early estate startups. So you've got to find these sales folks that are a bit of product savants and dropping the VP of sales in that isn't a product savant, which is a big issue. That's all mister or miss process. This is the issue. They're all mister or miss process.
So the second point I wanted to make, and I was on the fence for years of when you hire a VP of sales, do they need to carry a bag? Do they need to sell themselves or not? Does it matter? Does it matter? I wasn't sure for a long time. The reason I wasn't sure for a long time, it's not that you don't want a VP of sales carrying a bag. I do think a VP of engineering also should commit code. We can talk about that.

LennyCarrying a bag, meaning close sales themselves?

Jason LemkinYeah, not just be a boss.

LennyHave a quota.

Jason LemkinYeah, have a quote. The reason I was on the fence was because I was like, "Well, listen, in theory it's great, but let's say you're a hot startup and you want to go from two to six this year." So I want to add 4 million in new bookings, and let's say I can do 400K in quota per rep. That means I got to have 10 reps. She walks in with two. I'm at a race, aren't I? I got to hire eight in the next six months to hit my plan, and I got to put numbers on the board. If I'm going to out there as an individual contributor sales rep, I'm never going to hire eight people, am I? It's never going to happen.

So I used to say I don't know if it matters, but what I've learned the last 18 to 20 months when everyone has gotten lazy, Lenny, everyone in tech has gotten lazy, is I see way too many VPs of sales that come in and never have any idea how to sell the product, never, never. They only want to be managers.
Now, whether they carry a bag or whether what they do is they join calls with the reps, whether they backfill the reps, you want your VP of sales in deals 20, 30 hours a week when they start. I see VPs of sales today start, they're in no deals. I'll go to a board meeting and a VP of sales will be there two, three months, and they'll have a look on the board. I'm like, "How's it going with Airbnb?" and they'll be like, "I don't know. I got to ask John." Doesn't know because it isn't in the deal, isn't even in the deal. So I see this too often.
Another company I'm on the board on, I really like this VP of sales a lot. He joined and six months in, sales were down from where, the new bookings were down from where they were six months before. He was honest. He's like, "The biggest problem is I feel like I didn't have time to learn this product. It's a complicated product. It's more complicated than the product I last sold, and I just didn't have time."

LennyJason, this conversation is going exactly how I'd hoped. There's so much actionable advice here. Let me try to summarize a little bit of the things you've said and then keep going. So let me know what I'm missing here. I'm going to try to just highlight some of the important things you mentioned. So in terms of when it makes sense to start hiring your first salesperson, a couple of things you shared is you've closed the first 10 customers on your own as founders. If you're spending more than 20% of your time on sales and you need to start creating more leverage. I'll throw in one other thing I've heard and just to tell me if this is also true, that there's a repeatable process you've created. You can sell consistently enough or you can tell someone, "Here's how I've been selling." Is that right?

Jason LemkinYeah. If you hire a VP of sales before then, it's approaching 100% chance of failure.

LennyI see. So you can hire the first two reps before you're like, "Here's a pretty good process that has worked for me a number of times."

Jason LemkinYeah. Listen, as hard as it is for a lot of founders to even get their arms around, the reason is you've got to be that crummy first head of sales with them. You've got to manage those reps. You've got to be in the field with them. You've got to be figuring it out before you can hire the person. You just have to even if you're terrible at it because you're still going to be a good middler. You're still going to be a good middler.

LennyOkay. A few more things that stood out to me. One is hire two sales reps immediately, not just one. These reps you need to interview about 30 people. Eight will be pretty good, 20 will be terrible, and two, these are people that you can see selling your product and you would buy from them. They're often very quirky and not maybe a traditional sales background. They've never been VPs of sales, essentially. They're more like AEs and things like that historically or maybe not even salespeople historically. Is that right?

Jason LemkinI think you will regret it if you don't hire these first couple of sales reps that have a couple years of experience if you're in B2B with B2B sales. They need a couple of years of experience and they need a certain amount of maturity, and maturity is a real issue, and these are in any early hire because we just don't have time to babysit people. There's no onboarding, there's no training. So they need a couple years of experience, ideally something close to your deal size, we could chat about why, that would be nice, and enough maturity that you can trust them with that lead. You can trust them with your customer.

LennyOkay. Then you hire a VP of sales once you're ready to go from three to 300 reps. Your advice is also give the VP of sales a bag slash a quota slash they need to be doing sales themselves in today's world.

Jason LemkinAt least for a little while. More importantly, if they don't want to, I think in today's world you got to run from them. Exactly whether they fully carry a quota, a half quota, whether they backfill the sales team, you want a salesperson. Here's the thing, Lenny, you want a ... This is going to sound silly, but it's not. Trust me on this. For anyone watching, listening, you want a head of sales that actually wants to do sales. I got to tell you, and I'm still struggling with this myself after the last three years or so, so many folks in all functions, we could talk about other functions too, but especially in sales, don't want to do sales anymore. They don't want to do it. They don't want do it.

2021 was crazy because everything was too crazy. There's too much money, too much going on. 2022 was the knife falling. That was crazy too. 2023 was just hard. Whether it's burnout or whatever out or just too much change, I would say I've probably interviewed for different reasons, 50 VPs of sales in the last 12 months, I would say the majority don't want to do sales. It's my first screening question. That's why they got to carry a bag because it proves they actually still care about the craft.
The best sales folks love sales. It's a craft. They love money. Yes, they love money, and that does matter. Do not hire a sales rep that doesn't like money. Trust me on this one. There's 0% chance they'll work out either, but they also like the craft. They like honing the script. They like beating the competition. They like figuring out the counterfeit. They like figuring out the weapon and the 10x feature. They like working on a team. They like hunting. They love it, but then sometimes I just think burnout is always a reality, but I just think that the last three years have been so yo-yoed, that folks are just, they're out. They're out. Don't hire them no matter how smart they are, and that's the test.
I'll tell you, I talked with a really great VP of sales candidate that had worked with a top 10 tech company and I asked him what he wanted to do in this next role. He's like, "I've got a great team. I've got eight people that I can bring with me. We're ready to lock and load." I'm like, "Okay. Well, let me tell you one of my views in today's world is that you've got to actually visit more customers now, not less. In a distributed world, it's more important to visit customers." He lived in the East Bay in Pleasanton in the East Bay, which is maybe 20 minutes east of Oakland. He said, "I'm willing to visit customers, but I won't go as far as the peninsula in San Francisco." He's just happy at home. He's happy at home, Lenny, and he don't want to sell.
This guy has the best LinkedIn and the best references, but he don't want to sell anymore. He needs a job. He wants to be a VP of sales. I see this across the industry and I'm struggling to find answers. I think the biggest hiring ... We talked about a lot of tactical hiring mistakes that you can make today in sales. The biggest strategic mistake you can make today in sales because there's so many veterans, there's so many folks that worked at Twilio and Mongo and wherever, pick any great company you want. There's so many veterans out there, you just can't hire the ones that don't actually want to sell anymore, and there's too many, there's too many.

LennyYou mentioned that you actually just asked them in the interview. The first question is, "Do you actually want to sell?" What other questions do you ask for either ... Let's go through both. You said you have these questions that you ask for the early hires and then the VP of sales. What are some tips for people when they're interviewing these folks?

Jason LemkinIt's interesting. VP of sales or VP of product, I look for the same answer. One of the Colombo style questions I ask them, and this is so odd. It barely even counts as a question is, what do you want to do your first 30 days? What do you want to do? Actually, I usually ask, "What do you want to do your first two weeks?" In B2B, if I don't hear from the VP of sales or the VP of product that I'm going to go meet customers, out, I'm out. There's too many VPs of product too, Lenny, that don't want to meet customers anymore either. The majority of VPs of products that I interview, they don't meet customers. Every single great VP of product, chief product officer I've ever worked with in my entire career, you know what the first thing they do in the first two weeks? They're like, "Leave me alone. I'm going to go talk to 20 customers. Leave me alone."
The first two weeks, they're like, "Leave me alone. I'm going to go talk to 20 customers. Leave me alone. Leave me alone, I'm going to go talk..." They don't want to sit out on meetings and look at PRDs and talk out of their navel on endless internal meetings. All the best ones, they say they just leave. They literally say, "Leave me alone. I will see you in two weeks. I'm going to go meet with 20 customers." And that's what products should do. Sales, whether it's prospects or existing customers, it can vary, but they should be like, "On my first day, I want to join five calls."

And when you hear that story of, "I don't want to travel out of Pleasanton," or they say, here's what you're going to hear from the wrong person for anything, even up to 50 million in revenue, "I'm going to spend that first month working on process," "I'm going to spend that first month getting Salesforce up and running," "I'm going to send the first month on territory planning, Lenny, because we really, with our three reps, I really want to make sure we've nailed territories, right? Lenny will do the south, Elaine will do the east, Jason will do the west."
When you hear process, process, process, from any, from marketing, product, sales, customer success, too, boy, it's the death of customer success. It's just... And it's not that you don't need process, it's just, it's even worse than it was than a few years ago. And I know this is going to trigger some people, but the truth is they don't want to work. They don't want to work. They don't want to work.
I literally just got this LinkedIn email to work with me at SaaStr, from this person who'd been reading SaaStr for eight years. You're like, "I want to run account management, customer success for you. Here's what's, you're doing wrong, here's how to do it." I'm like, "Oh, this is pretty good." And I DMed her back, I'm like, "Great. To be honest, you realize that you're actually going to have to talk to customers and sponsors yourself in the beginning." No response. Just out. Just out. And that was the best one I got the last 30 days. That was the best inbound that I personally got.
I know it sounds triggering or critical, but as founders, we have to be honest that there's this vast pool of veterans with great LinkedIns and great resumes that are so burnt out, Lenny. And let's not blame them. I know it sounds like I'm blaming them or being negative, and I'm trying to not be negative. I'm empathetic. I am empathetic to the burnout, but don't, you can't hire these. There's too many.
The industry is littered with the burnt out. They're littered with it. And if you hear a touch of cynicism, if you hear anger, if you hear, "I don't want to meet customers in any..." and I'm going to say any VP role, product, sales, marketing, customers... If they don't want to meet customers their first, let's make it a 14-day test, you know they're never going to want to meet customers.

LennyThese folks that don't want to do sales that are VPs of sales, I imagine when you're further along, that's more, okay, because you don't need them to be doing sales, right? They want to manage, optimize. No. I see you shaking your head?

Jason LemkinI mean, okay, you think, okay, there's an element, let's call it north of 50 or 100 million, where for, what's sometimes called commercial sales, SMB sales, it really is all process. Okay? So for sure, I agree. But at Salesforce, they're trying to close $100-million-plus deals. You think that the sales leadership doesn't need to be in those deals? You think they can just hit refresh on the dashboards and track them from home? No. Marc Benioff today is still flying to meet customers. He said the other day, why does Marc Benioff go to Davos? He sits, and I've never been to Davos. He sits at the same place, at the top of some staircase. Okay?

And Salesforce drops millions of dollars, and he waits to meet customers, prospects, and partners in person all day, because it's efficient. Because it's efficient. Because he can do 50 or 100 customer or prospect meetings a day at Davos. He's still doing it at 30-something billion in revenue. Right? So this idea that, is there some truth at... For example, when I worked at Adobe back in the day, it is true that Adobe, which was, parts of the business, sales literally was dashboards. I get it. Okay, at four billion, 10 billion in revenue, but most of your audience is not ready to hire at four billion or 10 billion in revenue. They're not ready to hire that person. Don't hire them, right?

LennyI don't know, maybe Satya's listening. You never know.

Jason LemkinI think on the sales side of the business, they're flying out to the big deals?

LennyTo close the loop on this thread, when you're interviewing the early sales reps, those first two quirky folks, what are some questions and ways to know if there may be a good fit? You mentioned one of, you feel like you would buy from them?

Jason LemkinOkay. The one, really, the simplest one, and early in my career, I thought this was silly or hated it, this Glengarry Glen Ross. I don't know if it was Glengarry Glen Ross or that toxic Leo movie about sales, which is still entertaining. Yeah, one way or another, Lenny, it's got to be, "Sell me this pen." But it's not "Sell me this pen," it's "Sell me this app." So I don't like surprises, I don't like games. I like to do this in a second interview or whatever. Give them time. And I don't like to judge too harshly, but whether it's the first interview or the second, they got to sell you this pen. They've got to put in the 30 minutes of work and maybe it's two hours.

But here's the thing, today's world, you can go on YouTube or someone's website... There's an explainer video for every product under the sun, isn't there? I am shocked how many salespeople I have met, Lenny, from SDR to SEB of sales that, by the time... And I'm doing an interview for a portfolio company, this isn't a screener interview, they haven't even watched an explainer video yet. I could be the fifth or eighth interview, and they don't know how the product works. They have not even gone to the effort of searching YouTube or the homepage and watching it.
And forget about explainer videos enough. But so many companies do webinars now and they publish them on the... Really good stuff, customer testimonials. Right? If you're a sales rep, you don't actually have to know how the webhooks work or how to provision an API key, but you need to know the product as well as that webinar that's on YouTube. And 98 out of 100 folks won't bother in an interview. They won't bother. They're just going to click on "Apply" on the ATS and tell you, "Hey, I recently stumbled upon whatever. It looks like... Do you have time to discuss." Right?
But that one that actually does enough work and watches the video, and then can sell it to you, and they're going to make mistakes. They're not going to get it right, but they have enough confidence with the core problem to be solved. Because here's the mistake that 99% of founders and sales reps make. We're not really selling in B2B. We're solving problems. And this is why so many people are struggling in 2024, because they can't... their products, as sales reps, as companies, they can't solve big problems anymore.
Our job as sales reps in SaaS is to not sell a used car, okay? We are selling a Tesla Model 3 performance. It has competition. I might not need it this week, but it's pretty darn good. And I'm going to help you understand, Lenny, because you're in the market for the car, why this is the best one. I'm going to be honest about where it's not. I'm going to answer all your questions. I'm such an expert, and then I'm going to ask you, Lenny, when is that... You have 280,000 miles on the Civic? Let me help you get you into that Model 3 performance today. And I've even got a special discount for the end of this month. And let me just help you."
And I've spent four calls answering all your questions and I'm explained to you all the things and why the supercharging network is better than the regular one that doesn't really work at the charger near your house. And I've gone on Google and I've seen there's no charging network near your house, there's only supercharges. I got you, don't I? And that's the job of SaaS and sales, because we're not selling commodities. And that's why the best reps will also tell reps when not to buy their product.
As painful as that seems in tougher times, in 2024, the best reps say, "No, we're not there yet. We're not the right... If you need this feature, if you need this integration, I want you back in six months when you use this big product that isn't that great. But today, we're not the right solution for you." That's, the best ones do that. They have the confidence to know to close it. And the rest of the world thinks this is some sort of adversarial transactional thing and it's not. Right?
Software... I think hopefully all your audience would agree, when it's done right, software's magical. It solves incredible problems, incredible problems. What Airbnb does, what Uber does, what SaaS... Things solve... I can track my customers, I can manage, I can automate my communications. It's magical. You shouldn't have to use boiler room tactics and use tactics when you have something. But, it doesn't sell itself, except for a little while in late 2020, early 2021, that screwed the whole world up when products actually sold themselves.

LennyI feel like this is a separate podcast we should do of just how to get better at sales and how to sell. But, I feel like that's its own hour of conversation. I did a great episode with April Dunford where, I don't know if you follow her stuff, but she-

Jason LemkinYes.

Lenny... essentially describes exactly your approach of help people understand the market, help them understand the entire landscape, and then talk about your problem. So anyway, we'll link to that episode. Has a lot of good advice there. In terms of this interview, selling-me-a-pen approach, to give people something very concrete to do. How do you actually set this up? Is it like, "Sell me your product," and then they put together a pitch for your team and they pitch you on a product?

Jason LemkinI'll tell you, until the boom, until everyone in late 2020 got so desperate to hire anyone with a pulse, almost everyone in sales had to come and they had, during an interview process, they actually had to do the pitch. They would come and you used to do it in person with this screen. You can do it on Zoom now, it really doesn't matter, but do it for real. Do it for real, and everyone would see. And everyone in recruiting change, people stopped doing reference checks, they stopped doing these tests, and they would just hire warm bodies.

Late 2020, I can tell you a funny story in a second, and it was okay until it wasn't. And our hiring processes have not reverted back to pre-March, 2020, and I think it's failing founders left and right. I can't tell you, I would say 95% of the hiring I see out there, people don't do reference checks anymore, Lenny. And we can talk about when they work and when they don't, but no one does them. No one does them. You're going to invest so much... Forget about the salary, it doesn't really matter. So much time, your time, your leads, everything's so precious, to bring Jason into your company and you're going to go through all this recruiting process and you're not even going to do any reference checks? People don't even do reference checks.
And they don't, they stopped doing, "Do me this demo," because they were so worried the rep would go to Gusto or would go to Deal, or would go to remote. There was no time. I got to get... This SDR has 50 offers. Lenny, we got to hire this SDR with three weeks of experience. We've got to decide today. And that's the way, and hiring does not come back. If those hires bounce, not only is it bad for you, but it's a disservice to the... It's worse for the hire. I mean, that poor CloudFlare woman that blew up with the thing, there's so many issues there we could dig into, but it's all Cloudflare fault for hiring her. Okay, let's forget about that she didn't close a single deal. Okay, so objectively, in sales, should you retain your job in sales if you can't close a single deal? I don't want to get into some of the triggering things, but remember, if you hire someone and they fail, it's all your fault. She didn't know what she was getting herself into. No candidates can do enough diligence ever. There's not enough time. There isn't enough time.
And this is true all the way to the top. And so, as an investor, a board member, it's funny, when I do interviews, I do this thing, I try to be the last interview sometimes, and the founders don't want me to do it. They want me to sell. I don't want to be the last one. And what I want to do is when, Lenny, you've decided to join Ellen at her startup, right? At the end, I said, "Look, Lenny, I've talked to Ellen, she loves you. You have the job. You've got the job. What I don't want you to do, Lenny is bouncing three months after. So let's slow down, let's talk about the questions you have on your mind, and let's have a safe space where we can make sure you're going to be happy and successful there." Right?
And sometimes even the founders get mad at me for doing this, because sometimes, the candidate bails. But I'm like, "I know you're mad at me today, but it is your fault. A hundred percent your fault if any of your hires fail. Don't blame them. And I'm guilty of this. I get upset when people start and they don't give it their all or they don't do it. I mean, what if you hired someone for your podcast and they decided, "You know what? I don't want to do the podcast this week. I'm tired. I'll do it..." You're so mad at them, but you should've seen it during the hiring process. Right?
So, tying it back, that's why you've got to do this, "Sell me this pen." You've got to, before you hire the salesperson, have them sell your product real. Do the demo. And if they need more time, give them more time. Let them watch another demo. Don't have them feel like it's a trap or spook them. Treat them the way you would like to be treated. But if you skip this step, I mean, what's the point? You're not helping them.

LennyWhat I love about this process is it connects exactly to what you recommended you look for in these hires is, "Would I buy my product from these people?" So this makes a lot of sense. And you give them this assignment at home and they do work on this and they come in, right? It's not like come to the office?

Jason LemkinIf you talk to a great transactional VP of sales that's hiring tons of reps that do it, they'll make them do... If they're still doing this, they'll make you sell the pen fast in the process. They don't have time. They're doing 20 interviews a week, 30 interviews a week, you've got to sell me this pen. But if you're a founder and I'm talking about you've already talked to a bunch of candidates, you're down to one or two, make them, tell them, "Look, this isn't a trick. I'm not that great at telling my product myself, but I got to know that you're going to be happy and successful here. So do a demo for me."

And if they won't do it, they're not a salesperson. And too many people went into sales, not... The other weird thing about B2B sales in good times is actually, a lot of these folks are not really what you might think as salespeople. They can't do outbound, they can't pick up the phone. All they know how to do is to manage leads that come in and say, "I want to buy today." And you need those people, too. Okay? And I'm not saying you don't need those people, too, but that's not always what we think of as sales.

LennyAnother black box for me, and I think a lot of people with sales, is comp and quota, had actually set up their comp for early hires, and then how to actually decide on a quota. What advice do you have for figuring that out early on? What percentage is commission, what percentage is salary? All that-

Jason LemkinYeah, everyone gets this wrong. We worry... Look, at scale, when you're extremely mature, extremely mature, and very profitable, you really got to tweak this stuff very carefully, and we could talk about that if it's relevant. But, in the beginning, we get this all wrong. What matters is, can a sales rep close more than they take home? In the very beginning, that's all that matters. It's just you selling, right?

The first three months of a new rep, you're lucky if they can close as much as their take-home pay is, their OT. And so, in the really early days, my early, early day comp plan is, look, your first three months, you keep a hundred percent of what you close. Of course, that's not profitable for the business, but you've got to invest in them, right? You keep a hundred percent of what you close. And if you have enough going on in your business, usually, that's enough to put supper on the stove.

LennyAnd that's without a salary?

Jason LemkinNo, no. You pick an OT, a salary, but you got to... Okay, let's step back for a minute. You got to pay market. You got to pay market. And in the early days, if you're bootstrapped or really lean, this stresses folks out. I just talked to this great rep, Lenny, but he wants 150k OTE. And in fact, it's a step down. He had 170k at Slack, but he knows this isn't a startup. He wants 100. He might take 140.

LennyAnd OTE is total comp, overall total comp.

Jason LemkinTotal comp. And the founder panics. "I don't have, I'm only making 60. How can I pay 140?" Well, let's break it down for a minute. First of all, let's be tactical. It's usually 50/50, right? 50% base, 50% bonus for a sales rep. So they're really only taking home a 70k base, trying to make another 70. Okay? Then 70 divided by 12, help me do my math. It's not quite 6k month. Well, maybe with taxes it is. You're really only paying 6k a month for a couple months to see if this experiment works out. You're investing 20,000, you don't have $20,000 to do sales? Then don't do sales, if you can't find $20,000. So people freak out too much about this comp-line number, this base and bonus, the on-target earnings, OTE, and they're not more practical about what am I committing to cash upfront?

Two, you need a plan where it's a win-win. So if this person makes 140, but ultimately, a sales rep's got to bring in four to five times what they take home. That 140's got to be 500, 600 or more. The more enterprise you are, the bigger the multiple has to be, and the higher the comp. But it's got to be 3x to 5x at a minimum, 3x for small businesses, 4x for mid-market, 5... You got to get there, but you don't have to be there on day one and two. When you get there, the reps should be accretive, shouldn't they be? If they make 150 and they bring in 450, unless your marketing costs are out of control, which can happen, but that's not sales fault is it? If your marketing costs are reasonable and you pay a sales rep 150 for closing 450, if you engineer your plan right, you should be smiling, not frowning.
Where it gets tough is when you have a ton of folks not closing. When you have a ton of folks not closing and you have extremely high marketing costs, then it all breaks. Your cap breaks, your payback period breaks. But, if you have inbound leads, if you have demand, and you have sales reps that can sell you this pen, they're going to be accretive, Lenny, because of that math. And take the pressure off, don't make them close 5x their take on their first quarter, make them close 1x. Let them put points on board, let them eat. And so negotiating, here's the point if you think about it. Negotiating someone down from a 150k OTE to 130, it's not going to make any difference. You want them to close 600 or 700. It's not going to matter.
At scale, does it matter? For Mongo maybe. Maybe. But, what you care about is how much more can they close and they bring in? And then you, that's why you want them to make a lot of money. You want them to be rich. You want them to take home a lot for a whole bunch of reasons. And so, don't freak out about the acronym OTE, what they take home. Figure out what it's really going to cost you and would you buy from them? And if you would, they're probably going to bring in more than they take home. Right? And on the marketing side, in early days, you're lucky if you can find a marketing channel that is that accretive.

LennyAmazing. Okay. So just to summarize, you start a sales person with, say, 75k in salary and then say 75k in expected sales. And they take-

Jason LemkinBonus, bonus.

LennyBonus.

Jason LemkinBonus from sales, yep.

LennyBonus from sales and the the idea there is they take 100% initially of their sales, for the first month or two, just to make it feel amazing. They're making money. See how they're doing, don't put a lot of pressure on them. And then the plan is, over time, get it to a point where they're bringing into the business four to five times what they're taking home in terms of bonus.

Jason LemkinYeah, yeah.

LennyI set expectations every month or two, or is it every quarter? We're going to revisit your comp and quota and adjust.

Jason LemkinIf you get it right, you never have to revisit it. Not for years. I mean, I'm using the same sales comp plan I have for a lot of years. It still works. Listen, you can make tweaks and you've got to listen, and we're all human beings. And people, and again, remember, your sales team has to eat. They've got to eat, okay? And you've got to be somewhat competitive. But, there's only so much you can tweak, Lenny. I mean, they have to bring, close more than they bring home. Right?

And so, you can make tweaks at the margin. The problem is if you make too many tweaks to this model, you burn up all the cash. You're trying to plug a leaky boat, there's no point. There's no point. There's no point. And remember, related to this, for a long time, for most folks, unless you're, even if you're hyper funded, you're better off with fewer, better reps than more reps.
There is a stage when you get big enough where this concept of capacity planning really does matter. Lenny, if I got to go from 50 to 100 this year, okay? I'm going to add 50 million. If each of my reps can do 500k, I need a hundred, don't I? Okay. And literally, if you have 20, you mathematically cannot hit the plan. So there's a certain truth at scale. In the early days, this is a rookie error. I'd much rather have two reps, each closing a million than 20 reps struggling to close 100k each. Culturally, it's terrible. There's no domain knowledge in the company. Everyone's miserable, everyone's fighting.
What you want to do in the early days is concentrate your leads and your best closers, at the same time, bringing new people up. But you've got to concentrate your leads to your best closers. And that means year two, year three, year four, they should be making a lot of money. Lot of money, sometimes too much. I remember the first investment I ever made was a company called Pipedrive, which sold for a billion and a half. SMB CRM, and I put in the first sales rep there. He used to work for me. And the founders got mad at him. They got mad at him, because in three months, he was making more than any of the founders. They were pissed.
I'm like, "Guys, I know we're have different backgrounds and cultures, but this is what you want." But it took them a long time culturally as self-serve... Because Pipedrive was 100% self-serve at the time. They'd never had a sales rep. And I put the guy in, and what he did was he went and he looked, all these self-serve customers, he's like, this was the company was about two million revenue at the time. And he's like, "Okay, who's bought more than one seat?" He just did a reverse sort and he called them.
I remember he called AOL back in the day and he's like, "You guys have 20 seats of Pipedrive. Would you like to buy more for your sales team?" They're like, "Thank you very much. We'll take 100 seats." And he just went down the list, from the top to the bottom, and he took home 20% of those deals. Now that difference, that extra 80 seats at AOL, he brought it in. So Kim, keeping 20% of that is a great deal for the company, right? But he was pretty good at it and he was the only person for a while, so he made hundreds and hundreds of thousands of dollars when the poor company, the founders were paying themselves 50.

LennySo your advice there is don't be sad if your salesperson is making tons of money.

Jason LemkinIf you architect the simple sales fund we talked about, and they're making a lot of money, you're making a lot of money, and your equity is worth a lot of money, your equity is worth a lot of money. Right?

LennyWhen do you make that switch from they're taking home 100% of what they're selling to smaller percentage?

Jason LemkinLook, some people are going to think it's goofy what I said about 100. I just view it as a simple ramp. I think you do it for one quarter max. One quarter. The problem is if you let this go for too long, more than a quarter, if you make it too easy for long a quarter, the problem is the mediocre lean into it too much, and that doesn't help. And not only does it not help you, it doesn't help them. You don't want to make mishires. They're so damn... I mean, you could have a whole podcast only just on mishires. It's probably the single most important thing in scaling startups. It's not hires, it's mishires.

It's a tragedy if you mis-hire a rep, but you don't want them there six months. It's not good for them either. You want to support them, you want to help them find a place where they're successful. And here's the quirky thing on the mishires, and this is why that first guy I hired was mid-pack. He was less than mid-pack. Here's the thing about sales is, someone can be very good in certain sales environments and completely fail in other ones, completely fail. It's probably more binary than any other function. And so you got to find it before you hire them, but you also got to root it out fast, because those leads are too precious.
And it doesn't mean they won't go on to another company and be wildly successful, but you could utterly fail. And the one related point I'll give, if I had to throw one hint on this first, any of these reps, first 10 and VP of sales, one hint more than anything else, trust... got to hire someone whose last product was harder to sell. This is so important. This is a recipe for utter disaster. If you've, take someone in sales and their last product was easier to sell, they will have none of the skills to sell your product. But, this is the... and I'll give you an example in a second.
If you hire someone from something that was just a smidge harder, a smidge harder to sell, and they come into your company, it's like they're on Mars. It's like weight has been released from their feet. They learned how to sell a harder product and get it done, and then they come to you. And the first example I had, the first SDR I hired was a guy named Sam Blond, who went on to be CRO at Brex, and then now is a partner at Founders Fund. We worked together from the very beginning, first SDR. And he came, before that, he was an SDR at a company called Intacct, which was bought for a billion, which was online financials. Okay?
And back in the day, we know what the one thing people didn't want to put in their cloud was? Their financial statements, okay? It just wasn't trusted that. There are some things you would trust to the cloud, like A CRM, but they'd be like, "These are my crown jewels. I can't put these..." So he went from desperately trying to convince folks to move a business process to the cloud. They had no interest. And he came to us, and it was hard, but it wasn't that hard. And he instantly was number one. He went from SDR to SMB-AE to mid-market AE to director of sales, to head of this whole sale...
Because, I mean, there are many reasons he was great, but he came to me and I said, "Sam, why are you crushing it when everyone else here is struggling?" He's like, "This is much easier than Intacct." So hire someone like that and don't make... No matter how much you like them, the sell me this pen thing will control for it a bit, okay? But, when we give, we give, we give in the hiring process. We never give what we want. Be very, very careful if the last product was easier to sell.

LennyI love this advice. What is a heuristic that the last product was harder to sell than yours? What tells you that that's probably true?

Jason LemkinBe very careful if it was more technical, very technical. Some folks can go from a business process sale. They can go from selling a Gong or a sales software and outreach, and they can go sell a complicated API to VPs of engineering or VPs of product, but most can't. Okay? So more technical is a tough heuristic. More competitive is a positive. What really works, Lenny, is if you hire someone from the number four in the space and they did well. You take someone that was number four in the space and then you're number two in the space? You think number two's really hard because number one's crushing you? But they're at number four in a space where no one can tell the difference between these products? That's a great one, right? So a space that's more competitive, a space that is a positive, more technical.

The other one related to technical, on the pure B2B side, is much more complicated business process. I see folks fail in B2B when they've sold us... Yeah, it's hard, but they've sold a simple business process. They go to something that's got a lot of integrations, a lot of complexity, and a lot of business process change, and they just melt because it's too complicated. They just melt, right? There's a company I invested in, it's doing over 20 million today. And for some reason, to simplify what they do, which is pretty complicated, they called it the Gong for X. Okay? The Gong for X.
And it's great to get a VC meeting and a few other, but it's not even on their homepage, okay? It doesn't really make sense. And the CEO had me listen to this senior sales exec he hired, and the only thing he could tell the prospect was that they were Gong for X. And the prospect kept asking, "Well, how does this deep integration with this business process flow and Zendesk works, and how does this go over to Salesforce?" He's like, "Well, we're Gong for X." That $600,000 deal was lost. Right?
But, maybe that works in some space, right? And Gong's hard to sell today, too, don't get me wrong. But you see my point, it's just that simplicity, it's too complicated, right? And I know it's not the perfect heuristic, other than this technical thing, but the technical one, man, trust me. Too many B2B type reps melt in B2D. They just melt. They just, selling to VP of eng is a different... It's the same beast, but they don't suffer fools, do they? Not the VP of engineerings I'm close. They don't suffer fools.

LennyI haven't heard this term, B2D before, business to developers.

Jason LemkinTo developer, yeah.

LennyI imagine that what it stands for. Oh, interesting. Haven't heard that term before. Okay, let me zoom out a bit and I want to move on to a different topic. But before we do that, so we've talked about kind of these early days of hiring your first two reps, getting your VP of sales to help scale out the team. To give people a sense of where this goes, as the business scales, what does the org evolution look like? You have these two reps doing sales on their own, then you have a manager. What does it look like over the next couple phases of the sales org?

Jason LemkinLook, to simplify, there's rules of eight. So in sales, I'm actually not sure what the tip of heuristic is in product, because product teams are leaner, at least I hope. I like it when they're leaner. But the thing about sales is there's no efficiency. If you have a sales-led motion, half your company is going to be in sales at 10 millionaire, half your company is going to be in sales at 50, half your company is going to be in sales at 100.

One of the tough parts of the software model is that there's no, there's actually almost anti-efficiencies in sales. The public companies are actually less, they have the higher CACs than startups, believe it or not, because they have so much market penetration. So you're going to need a lot of people. And it's rules of eight, eight SDRs, outbound reps need one manager, eight AEs, eight sales execs need a director above them.
And then when you really scale, eight directors. You don't really ever going to have eight directors, but eight directors could have a VP or eight reports. And so there's rules of eight. If you want to build an organization on it, it's all rules of eight. For a while, for SDRs, thinking this was this high velocity entry-level position, people pushed it to 12. But the more folks I talk to today, the more I hear, everyone's reverted to eight. I'd rather have fewer SDRs, having better conversations. And so it's just, you can build your whole org with eights.

LennyThat is way too easy of an answer. So the idea there is you hire this VP of sales, then you hire six more sales reps, AEs. So what happens next? You hire another-

Jason LemkinGot to start hiring managers.

LennyManager, got it. Yeah.

Jason LemkinYeah.

LennyAnd then you scale eight more reps.

Jason LemkinAnd once you have eight AEs scaled, you almost always are going to start, a VP's going to already... A good VP of sales already be hunting two directors.

LennyTwo directors.

Jason LemkinWhether they're just split up normally, whether they're east, west is a classic way. Another way, you might have smaller and larger customers. That's pretty standard, right? Commercial and enterprise. But a good VP of sales, once you have, she or he has eight reports, will be bringing in two directors, or maybe two VPs if they're an SVP. There's a lot of title-
... directors or maybe two VPs if they're an SVP. There's a lot of title inflation today, which doesn't bother me nearly as much as a lot of other things we've chatted about. I don't care what your title is if you'll actually do sales or do work, but yeah, we need to bring in managers at 8:00. And folks that can, also, a related point is, a lot of founders were, "When will my ... " I really love my head of sales, but she's a stretch. Most of them should be stretches.

If you hire the seasoned one, they're not going to work, so for 95 out of 100 of us, our first head of sales should be a stretch VP of Sales. And what that means is, usually, they were a director before that or a senior director or sort of a VP, okay? But you should be cautious about hiring your first VP of Sales for their first third VP of Sales gig. They're not willing to do the job anymore. You need a stretch and it's worth it for their career growth. It's worth it for their personal growth. It's worth it for the equity, right? So you're going to hire a stretch. That's an important tip right there. But then, you're going to be a little worried, how far can Lenny go? How far can ... I love Lenny, but he was a director for two years before this, and this is his first rule, and he did so good last year, but I'm worried Lenny's going to break. I'm worried Lenny's going to break.
And related to this quote, the simple answer is, Lenny will break if he can't source those directors under him. You can scale forever as a sales leader if you can hire better managers under you. And it's true of any functional area, but what you'll see in sales is, you'll see your stretch VP of Sales drown when they never can hire better managers under them, They'll end up doing some weird internal promotions, which you want, you want to do internal promotions. My rule is you want to promote 50% from within and hire 50% without for your managers, but if, really, the only people you can promote are just junior people on your team, you can't find leaders, you can't scale. I do see this happen too frequently is, a first time out of sales, does it, and then, they're like, "Here are my managers, Lorraine and Jason, but they really were just reps for two years and they don't know how to do it." So you have a whole bunch of people who don't know how to do it. That's when the organization cracks.

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There's these terms that we throw, around account executive reps. It might be helpful just to give people a sense of what does this actually mean when someone's an account executive. Is it that they're just sitting there calling and doing sales directly? Whatever the key terms are for the roles or the title might be helpful to quickly summarize.

Jason LemkinYeah, I think the two ones that are probably less obvious for folks that are new are SDR, Sales development representative, and AE, account executive.

LennyOkay, great.

Jason LemkinAnd SDR is, generally, although I wish it wasn't, it is generally an entry level position, often fresh out of school, generally paid on the order of 60K to 80K, OTE and SaaS and US-based SaaS, and their job is to email for dollars, dial for dollars, and in many cases, to screen, to screen inbound leads. It's entry level, and their job is to pass on a lead to a sales executive, an account executive, an AE. Not all companies have SDRs. It's a longer topic, but pretty much all the best teams have some type of SDR function now because we've learned we want to specialize. We want openers opening and we want closers closing, so that's the rough idea.

SDRs are openers in some cases, and account executives are the more seasoned folks closing. And it varies, compensation from account executives that are US-based could be anywhere from like 90K to 200K, depending on, that's with base and bonus split at 50/50, depending on whether they're hunting tiny deals or big ones. That's the way an account executive works. And I think what doesn't happen today ... Those are the acronyms, SDR and AE. I think people can figure out VP of Sales, that's vice president of sales.
I think a thing that's gone on in the industry that founders expect now because there's so much discussion of it on LinkedIn and social media, but I haven't found work, is that an account executive will magically be full stack. They will do outbound themselves, they'll go use ZoomInfo and Apollo and develop a list themselves, they'll manage that outbound list themselves. If they don't have enough inbound, in their free time, you know what they'll do, Lenny, in their free time? They'll just do more outbound. You know what sales reps do in their free time? Today, they sell real estate or courses.
If you want a tip, for founders, I know you want this full stack AE, and they do exist when they're micromanaged in certain high performance sales organizations, but they don't exist in real life. They're specialized. Most AEs, they want to be closers, they want to be handed a lead, a contact me, a lead. They want to work the lead and close the lead, and you hire some SDRs to help generate more demand. Those are the basic acronyms. What's hard for most founders, here's the tough part, most founders have enough stamina to manage a couple of these AEs, these account executives, these folks who work the leads. Most founders do not have the stamina to manage 10 kids fresh out of college that need to be micromanaged on an hourly basis to call leads. Very, very few founders themselves can manage a team of SDRs, but if you can, it's like a superpower.

LennyThat was really helpful. I did not know what exactly these terms represented, and when you're hiring those first two reps, they should be at the account executive level.

Jason LemkinYes. And they'll do some outbound and they'll do some of this SDR work. It's just, ultimately, people end up specializing.

LennyWhat is the title for someone above the account executive? Is it Director of Sales?

Jason LemkinYeah. There's really no ... It's a meta topic. I wish there were another career path for these ICs. This does exist in product, it does exist in engineering. It should exist in sales, but the truth is it doesn't. There is no senior SDR for this outbound. And for this AE, this person closing, yes, you can go more enterprise and make more money, but there isn't really a senior AE track, but there should be. It's unfortunate. It should be.

Too many of these folks are looking for, they look to go into management for promotion when what they really should look for is to be a super IC, and it's a shame that more folks don't try to implement a super IC role in sales, but that's basically what the career path is in management. And that's why another tip, another mistake that founders often make is, they hire the number one account executive at a hot company to be their head of sales. It's not the same skills. Most sales executives should not be managers. They don't want to be managers. They want to be individuals. They want to be highly paid individual contributors, these days, that mostly work from home and make a lot of money working 30 hours a week. That does not naturally breed great management skills.

LennyI want to shift directions a little bit and talk about product and sales. A lot of listeners of this podcast are product managers or founders building products. How involved should product managers be in sales. And vice versa, how involved should sales be in the roadmap and what's being built?

Jason LemkinI think, in the best run B2B organizations that I've worked with, and my own as well, the great, at least the head of product, the VP of Products, are deeply involved in sales. Deeply involved in sales. Deeply involved in sales. A company I invested in that's just crossing $60 million, they just had a meeting with who will be their largest customer. And the head of product who was there at the board meeting is like, "Thank God I was there because what they want to do with our product, we sort of do. We sort of." Now, the product does do it, but what they want to basically do is deconstruct the product. They don't actually want to use the backend and analytics and some other pieces, but they don't really need the front end of the product. If the head of product hadn't been there, that deal would've been lost. It would've been lost.

An AE doesn't know that. Even if an AE did know that, a sales rep did know that even. If the VP of Sales didn't know ... A VP of Sales would not be empowered enough to stand up in a meeting and say, "I know what you want. We can launch tomorrow on this and, in 90 days, we'll tweak the UI so it does exactly what you want." You want that in your big deals. If you have that magical VP of Product that truly owns the roadmap, owns it and has the gravitas for that meeting, they become like the mini CEO in these meetings. A lot of CEOs, at scale, I've talked to, I was just talking with Daniel Chait at Greenhouse, he does this, they're over $200 million, when they have that head of product, they divide and conquer with the big customers. And the CEO can do some and the VP of product can do others.
And sometimes, the VP of Eng, if they're very producty, can also do that role too. Sometimes, you get these three weapons. In the old days, sometimes, your VP of Customer Success could do this, but unfortunately, and I know this is going to trigger some people, I don't see customer success stepping up for this pseudo product role anymore and I see them shrinking more and more into process. But that magical VP product, they give you that scale, that CEO level scale.
Can a product manager or a director do that? In my experience, the best ones, absolutely. The mid-pack ones that are working on the color of the pixel, I'd rather not have them in the deal. You have to be utterly fluent in the product, the entire product. You have to be the one that knows how to connect the pieces that don't ought to always connect themselves, and you have to have the gravitas to work with a large customer, to make commitments. That deep knowledge and commitment, it's hard below the VP level, but if it does exist, I love it. They become one of the greatest strategic weapons of a B2B company is bringing the product team, because the VP of Sales never quite goes that deep and can't make the commits, and the CEO can't be everywhere.

LennyThe bane of many product managers' existence is the flip side of sales is involvement in product. Do you have any advice for how you've seen the best SaaS companies handle requests from sales going into product, how product teams should think about requests from sales and making that work?

Jason LemkinI think this one is so simple and I'm surprised people make it so complicated. I know we all release 28 times a day, but the reality is, software still goes on quarterly release cycles no matter what we say, okay? Your customers cannot process 88 releases a day, okay? The maximum a customer can process is two big releases a year and maybe quarterly, so let's simplify. That's how customers think. Forget about how we build software.

Every quarter, give your head of sales a certain budget, whether it's story points or 10% of the pie chart, however you do it, give them a budget. And when you do this, things will radically change then. They radically change because even the best VPs of sales, they change the wind. On Monday, what they really need is the HubSpot integration. And they're like, "Oh, my god. We weren't going to do that for two years, but I guess we could change everything on Monday," but then, on Wednesday, a new prospect comes in and, "We need SAP, but we just spent two days spec-ing out." You need SAP. And then, on Monday, it's Salesforce, right? And it's not that sales isn't honest, it's just, the big deals, the big ones always, the tail's wagging the dog and it burns out the organization. Even with the best sales leaders, I find it burns out, especially because the stressful deals, they overreact, and as good as they are, they're not product people, so they don't really know how to prioritize and force rank. If you say, "Okay, Lenny, my VP of Sales, great. HubSpot, SAP, whatever you want, you've got 10% of the budget, you've got a hundred story points, whatever metric or heuristic you use, but you've got to decide now each quarter." And if you want to change during the course of the quarter, if you want to disrupt our whole engineering product team, you can do it, but understand there's a high cost, and the later you do it in the quarter, the less successful it's going to be because we already started the HubSpot integration. Not only will it demoralize the team, but we're going to run out of ... You already used your budget.
I just don't see enough product leaders being objective here, saying, "Listen, here's your budget. You get it, period. No one can take it from you. I guess the CO can steal it if she really wants to, but it's yours, VP of Sales." And they will do the low balancing across their team. They will do it. They will listen and they'll say, "Maybe I don't need that HubSpot integration after all. Maybe." Right?
Because what a VP of Sales should be doing is taking ... The CO has to look five years into the future, product has to look about two years into the future, and you really can't ask a VP of Sales to look more than 12 months into the future because that's where they're next on the line, but a good one will load balance feature requests across the year and they will listen to all the ... Because they'll actually be in sales, they'll actually be in deals, and they'll be listening and they'll realize, look, even though we're going to lose this deal to HubSpot, I've gotten four SAP requests the last ... I'm going to take that bet. Even if I'm wrong, I'm going to take that bet. You got to give them that ... And you got to talk about it every week and say, "Look, here's your budget, Jane. Here's your story points, your whatever, your 10%. This is what we're building now for you, objectively, and this is what we're currently planning for the next two quarters. Would you like to change the ones for the next two quarters? Because we haven't committed any code yet, and if you really want to change what's in process, you can. Otherwise, it's going to be hyper disruptive," but you got to at least pretend to be objective, for sales.
If you're too emotional about it, you break the organization. You've got to say, "Listen, I know we've already written 80% of this upside integration. If you really need us to put us on the shelf and drop everything for a million dollar deal, we're a startup, we'll do it. But understand, just, is this really really what you want?" And if you involve them every week as a stakeholder, magic happens. But I don't see the VPs of Product that I work with, I know I'm not in all the staff meetings, but the meetings I'm in and the board meetings, I don't see this back and forth happening.

LennyThis might be the same exact answer you just gave, but say you're a PM and a salesperson comes to you, "Hey, we're about to close this deal. We just need this one feature. Can we just get this on the roadmap?," what's the best way to help that sales person understand why it's not happening, help them feel like, "Okay, I get it"? Is it exactly what just said? "Okay, we could change everything. Here's the story points you have this quarter."

Jason LemkinWell, are you assuming that PM is the head of product or empowered enough to make the decisions?

LennyI'd say, yeah, that PM could put something on the roadmap if they think it's important.

Jason LemkinThe reason I'm a little confused, just because I want to get it right, is what I'm hearing, which maybe isn't what you said. What I'm hearing is, a junior IC rep is talking to a more mid-level product person about the roadmap, and you want to have that. That's one of the reasons we actually go to the office. Because those discussions don't happen on Zoom, Lenny. They don't happen. And you want those discussions to happen, but you don't actually want them empowered. You want them to say, "Listen, I will talk to my boss." That's the right answer. It's too confusing.

This stress between product and sales is a good thing. It's a sign of a well-run B2B company when there is stress between product and sales. It's a good sign. If there's no stress, you're not in enough deals. You're not in enough deals if there's no stress. But the stress has to have enough process, even in a startup, that it doesn't break because your question alludes to the fact it can break organizations again and again. People get people resented on either side.
This is one thing where the answer has to be, "Look, we can chat about it over lunch. We can chat about this, and actually, you've got a good idea. You're an individual contributor. I'm going to tell my boss, on Monday, that I think we should do that. I'm going to use a little social capital and say we should do this," but you got to push the decisions up. That's as far as you're going to make recommendations. Otherwise, instead of that one stressful conversation with the VP, you've got a hundred, you've got 10 times a hundred, and again, they're fun lunch conversations, but they'll wreck you.

LennySo the advice there is, basically, "Talk to your manager, I'll talk to my manager. They need to hash this out. It's not my call."

Jason LemkinI think you got to push it up and I think you got to force the VP of Sales and the VP of Product to have this weekly meeting about the budget, and that will force them to have enough, just enough organization on their team so that it can all be surfaced up. Because that means they each have to have a meeting with their team for 30 minutes each week and say, "I'm going to put up on the whiteboard guys, so my sales team's going to say ... And I've been to many of these meetings where you force the sales team to force rank what they want and you end up, I tell you, Lenny, 100% of the time in the sales meeting, when you do a whiteboard force rank, you end up walking out with very different outputs than when you start the meeting in sales 100% of the time.

On the product side, you need to do the converse. You just need to say, "We owe sales 10% of our points, so in our team meeting, we're going to put in 15 minutes of our team meeting and we're going to make sure we have the priorities right from the sales team. Let's go over what I got from Linda. This is what she says. Is she wrong? Should we do something? How can we help the sales team be even more successful? And what inputs is the team hearing?" And they can raise their hand and say, "Look, I just had this all the way conversation with Bobby, but honestly, Lenny, I can build a HubSpot integration in a day." "What? I thought it was really hard." "No, I did it my last company. And listen, actually, we can actually outsource it to Bob and Linda at this agency I know for 20 grand. They'll build it next week." That's a magical moment. That's a magical moment. But you've got to each have these parallel meetings. The good thing, that tension can become debilitating. We've all seen those fights, those almost fights that break out, and they come from a place of passion, but you got to have structure.

LennyGreat advice. Another trend I've been noticing is that product teams are taking on P&L responsibilities and revenue goals. What's your sense of, is that good? Is that bad? How do you think about that for product teams?

Jason LemkinYou want everyone to be aligned on the big picture revenue goal for the end of the year. Is the question, you mean having financial bonuses and stuff tied to hitting the plan?

LennyMore that their KPIs and their OKRs are essentially this much revenue, you need to drive this much revenue from your experiments, from your product launches.

Jason LemkinAs you can see, I have a lot of opinions on things here that are data-driven and they're live experience. This one, I need another year in the oven, and I'll tell you why. I'll tell you why. What happened in the last 18 months is, in customer success, which is, in the old days, it was related to product. Now, it's less so, which I think is unfortunate. In customer success, in the last 18 months, this happened all across the industry. 24 months ago, customer success's goal was happy customers, measured in retention, sometimes NRR, net retention with upsells, sometimes with GRR, just logos, how many logos. That was your only job, happy customers. Happy customers.

Then, things got harder in many areas of B2B, and every customer success team last year, their goal was revenue. You need to bring in more revenue from existing base, and it destroyed customer relationships. There is a leading public company, I will not name them, I'm a positive guy. I will tell you, a company we all have used for years and loved, and they did this to their customer success team. And they came to us last year, we paid $299 a month for this product for our team. They asked us for $50,000 upfront or said they would turn it off that day. That week. Maybe it was that week. $50,000. That's what happens when you weaponize ...
So customer success, and I know this is going to trigger some people, but it is true, when I talk to leaders, customer success got weaponized and I don't like it, okay? I don't like it as a product. All founders are product people, I think. I don't like it as a product because I think it's bad for customers. That experience I got was horrific, wasn't it? That $50,000, being told. And it got walked back. And the fact that it got walked back is almost even worse because it wasn't true. It was a threat. So do I want to weaponize the product team? I want the product team aligned with revenue. These are the tough decisions for founders. But I think we're going to regret, to some extent, weaponizing teams that we don't need to weaponize.
Having said that, I will tell you, and again, no knock on Adobe, but when I was a VP at Adobe, and it was a long time ago, when product was in another building, in some cases, that was not great. And I love Scott and the whole team, it was a great experience, but I can just tell you, what I learned is, that did not work for me as an agile guy, having groups that would do this work in isolation.
And the problem was they would never talk to a customer. So I know I want product constantly talking to the customer. I know I want the VP of product with a lot of equity, wanting to hit the bookings number for the year. Do I want your average PM weaponized and forced to bring in revenue from an experimental feature when everyone agreed it's the test we're going to run? We only can run so many. You say, should they have revenue for new feature launches, for new product expansions, for new things? Yes, but everyone's got to make that decision. There aren't that many of us that have 1,000 extra engineers sitting around with nothing to do.
Even the smallest experiment, no matter what it says on the internet, again, that we release 100 a day, I would argue bringing any product extension to market's very expensive and risky because you're taking away from something else. These are expensive decisions, and if you punish people for the mistakes in product, this is something that big companies are actually better at than startups, which is, they don't fire you if the new initiative fails. Because then, no one at a big company would ever join the new initiative. There are exceptions, but no one at Adobe or Google would work on the new product if you got fired if it didn't hit $100 million its first year.
One thing I saw that was very, and I don't know how to bring to startups in my big company experience, was it's liberating to some extent to let people fail, up to a point. It's liberating. Because the cost of failure in a startup is so high. It's just so high. I know that's not what the exact question, and ask me in a year, but my advice is, just be careful that you don't weaponize functions.

LennyI probably should have clarified. I think this is mostly true in PLG companies where most of the growth is coming from product, but I imagine the advice is still the same, as be careful putting too much pressure on the product team to focus on revenue.

Jason LemkinWell, that's how you get dark stuff. Back in the day, I remember my sister worked at Vistaprint for online business cards, and her entire job was to force people to buy upsell of additional products on the checkout page they didn't want to buy. That was her whole job. And she was paid a large variable comp to get people to buy third party products without realizing in their checkout, and it worked. That's all she did for three years was figure out dark stuff, I mean, darkish, grayish stuff so that when I bought my business card, I also bought GoDaddy and 11 other things that I didn't want. It works, but it doesn't create high NPS, does it?

LennyMm-hmm. No.

Jason LemkinThe thing is, here's the thing that you have to think about. What's crazy, Lenny, now, and I talk to a lot of these folks is, there's so many SaaS companies that are a billion or more in revenue. I just wrote up, there's just Pimcore, which is SaaS for . I just wrote up, it just crossed a billion in revenue. So many folks are at a billion. CloudFlare just crossed a billion. And the only way you can do that is if your revenue compounds.

And in fact, just myself, I just interviewed Matt Mullen from WordPress, 20 years he's been doing this, and he said the number one thing he didn't understand at WordPress, at Automatic, was the power of compounding. When you do these things that are customer hostile, and a lot of us were under stress this last 12 days, to hit the numbers, right? This is your job as founders, is you got to load balance the fact that the cash has to last and my investors are mad with me, but nothing matters in B2B that it compounds. And some of this dark stuff you're talking about on PLG, it anti-compounds, right?
And I would say, let me flip it around. The magical thing at the high level that it compounds, if you have a self-service model, a PLG model, I actually think the number one most important metric is churn. It's going to this churn, churn, churn, churn. And when I meet any startup for investing or anything, if the churn is not top decile for a low end product, I'm always out. It's almost unsolvable. It's almost unsolvable. This 3% to 4% a month churn rate that a lot of SMB stuff, it's almost unsolvable. I think that's where the energy should go, is relentlessly bringing down churn so that, 20 years from now, we all have billion dollar AR companies. That's what we want.

LennyI have a rapid fire set of questions before, actually, the lightning round. We'll see if we have time for all these things. I just have a bunch of random questions that I'm going to fire at you and and see what comes up. Sounds good? Okay, cool. I got a thumbs up. Let's do it. Okay.

What is just one thing a founder or product leader can do to become better at sales?

Jason LemkinThe number one thing they can do, and this is very tactical, at the end of each meeting, because again, both of them are good middlers, the head of product and the founders are good demos, they're good at talking shop, they're good at talking in the industry, they're good at talking workflows. Learn. This is the only school you have to learn. Even if you're not comfortable asking for money, learn to ask for what's the next step, Lenny. This is what all great salespeople have learned to do. Actually, mediocre salespeople are terrible at this. The best salespeople never leave a meeting without a next step. The next step does not have to be a check. Don't break the relationship, but what's the next meeting? The next meeting might be, "Lenny, is there someone else at your company that I could do a demo for?" People are lazy, they don't want to do multiple demos.

But in 2024, we all have to demo multiple stakeholders. In 2021, it was one stakeholder. Now, it's a four-stakeholder sale. If you don't know what to ask at the end of the call, ask, "Who else? Lenny, is there someone else? I know you're excited to buy our product, but who else? Is there someone else in the organization? Can I help you? Can I just do a demo?" A demo is not threatening. Whatever the next step is, "What's the next step we can get on our books?" And listen. The best salespeople march deals step by step by step by step. And then, they put in the time. They've done the demos, they've done the pilot if they need to, they've helped them get going, they've helped them see the value. And then, if it takes six steps to say, "Okay, Lenny, now, we've got five folks at the organization using it. They've seen, here's the deal. They love it. What can we do, Lenny, to get going? Can we get a contract signed so we can get going on February 1st?" It's just very natural.
And founders just end the Zoom. They end the zoom, and they wait. They wait in their inbox for the next step to come, but it doesn't, it rarely comes on its own. That's the number one tip is, make sure yourself and you log it in your CRM that you always have a next step after. You don't have to be great at sales. As long as you're moving the ball down the field, then, get it into the red zone, and then, figure out how to ask for the money. But you don't have to ask for the money until it's in the red zone.

LennyAmazing. While we're on this topic, is there a book or a course or anything that you'd just recommend folks go to get better at sales? Just, is there some tactical, "Go read this thing, it'll help you?" Or is it just, it's hard, you're not going to figure it out reading a book?

Jason LemkinI am a voracious reader. If I only wanted to plug myself, and I usually wouldn't, two things that we have, we have something called SaaStr.University. SaaStr dot University. It's free. There's a pretty good course on learning about sales. It's not perfect, but it's pretty good. It just organizes a lot of the stuff we're talking about and it's free. I think it's pretty helpful. We actually wrote a book called From Impossible To Inevitable that sold about 100,000 copies.

LennyOh, wow.

Jason LemkinI did almost none of the work, although a lot of is my content. Aaron Ross did it. It's actually really good, and it interviews a lot of top sales leaders and goes through a lot of stuff we did. I don't usually hype it, but for 15 bucks, I think this ... And actually, I've never made one dollar. I've never even gotten a check for these 100,000 copies, but I do think it's actually ... The second edition's pretty good. I think, if you like what we're talking about, the SaaS University and the others. I just hyped my own course, which is free. I don't think I'm selling something if it's free. The book, I don't make a dollar on. I'd be very cautious, and this is tough, maybe this is something we can work on together. There's so many courses and so many people selling stuff the last two years. Just be cautious. Just be cautious.

The last thing I will say is, there is another community called Pavilion, and I do think it's great, Pavilion. It does have a lot of networking and stuff for sales and connecting sales with founders, and I am a super fan of what they're doing. That one's worth investing. But be careful about Bob and John's sales courses on the internet. There's too many.

LennyAwesome. All right. We'll link to all those things in the show notes.

Next question, what is the ideal trial length for a free trial for sales team? Is it 14 days, a month, years? What do you recommend?

Jason LemkinTomas Tsangaris did a whole SaaStr presentation just on free trials and free trial legs. It was really good, but the one thing you didn't know, which I know just being an old timer is, one of the reasons we have 14-day trials on the internet is, in the old days, the Salesforce sales team, when they were SMB focused, wanted to close deals that month, so they forced Salesforce to move from 30 to 14 days. There was no evidence it was better for the customer. There was no evidence that it got usage going or people ... They just wanted to close deals the same month.

That's something to be cautious about, these metrics. And be cautious, since we're talking to product folks, be cautious that they're customer centric. Salesforce is very enterprise now, but in the old days, it pushed it to 14 days so the sales reps could close deals faster. What we learned from Slack and Zoom until recently was infinite trials work pretty good. So does Canva. Slack and Canva, and until recently, Zoom, were okay waiting four years to convert. And those are epic companies. Those are epic companies.
And these are one of the things that only founders can make these decisions. I wrote this post years ago saying, "Who's your VP of Free?" Because who's got a VP of Free? Do you know anybody that has a VP of Free? I got a VP of Growth, I got a VP of Product, but if you have this massive free base, who's your VP of Free? I know almost no one that has a VP of Free. And usually, it's some kind of collaboration between product and the CEO. They're the VP of Free, but even then, you need a VP of Free, and we don't have one. There's no perfect answers, but in a world where we're tightening nooses everywhere on trials, we're tightening nooses everywhere, be careful the advice you get, be careful the short-term advice.
For example, another related terrible piece of advice VCs give you is switch to annual contracts. This is terrible advice. Terrible advice, Lenny. Terrible advice from people who've never built products and aren't in the field. Going to annual contracts, on a spreadsheet, looks great. On a spreadsheet-

Jason LemkinGoing to annual contracts on a spreadsheet looks great. On a spreadsheet, it looks great. You know what's better? Letting customers pay what they want to pay. If it's you or me buying for ourselves, Lenny, we're still going to put it on a credit card, aren't we? If it's our own personal... And we want to pay monthly, usually, we don't know. We usually want to just try it monthly. Big companies want to pay annually because they have procurement departments. Why force people to go the way they don't want to go? So, just start, this is a product audience. Product needs to be the voice of the customer. It's not so much customer success as it used to be. It's not so much sales. You've got to be the voice of the customer together with the founders and push these things.

Think about, I would do the longest possible trial that is still customer-centric and understand there's tension. Understand there's tension, right? I say anytime I'm in a board meeting where some VC says, "Let's do annual for an SMB." I mean, I'm like, "No. Show me the money. Show me the evidence that this is better for the customer." Right? How many times have you gone to buy something for yourself and it's 19 bucks a month? And that's annoying because it's an credit card charge. But do you want to pay 240 up front? I mean, maybe you do it for a Riverside or something you use all the time, but some random product you just discovered, you're just going to bounce.

LennyYeah.

Jason LemkinSo, who's going to show the data in the bounce, right? A related point for like in sales. No one does enough. Everyone does these win-loss meetings, but no one talks enough about the deals they lost. Everyone talks about the deals they won. All the lore, the tribal lore in sales is how we won the deal. People should be spending more time talking about deals they lost than the deals they won, right? And same thing for this PLG motion. If you make your... Yes, I give everyone a pass for 2023, everyone whose growth plummeted and did things they shouldn't. Did price increases they didn't earn, cut the free trials, hid their free editions. I'm going to give you, look, you've got to give your team a little stress relief, right? So, I'm giving every person I work with, every portfolio, everyone a one-year pass, but the past is in the past. We got to get back to being customer-centric and building businesses that build to 1 billion ARR on their own because they're wonderful businesses that are product-centric, right? That recur. And every time you rip a customer off, you lose, the relationship's damaged, isn't it?

And a controversial thing I say to the product team, but I think this is the right thing if you're going long, is look, everyone raised prices last year, as you know, right? Everyone raised prices. The question I ask folks is, "Did you earn it?" What feature did you ? If you raised prices 8% last year, did you add 30% more value to your product? In the old days pre these crazy years, the answer usually was yes. People would wait up, they would wait a couple years, right? And the whatever product from four years ago was so much better. It really was. Really had earned 1995 instead of... Last year, no one earned their price increases. No one came out with an amazing new edition, an amazing new functionality that earned it. They just sent you an email saying, "You're paying more." So we get one pass, but earn it. Earn your price increase.

LennyAlmost 600,000.

Jason LemkinOkay. 600,000. Now, not all of them convert, do they?

LennyNo, no. That's exactly how I look at it. It's kind of this Brian Belfort is this... Yeah.

Jason LemkinWhat about the 590,000 of them that love Lenny that don't convert, right?

LennyYeah.

Jason LemkinIf you over monetize them, then Lenny's community doesn't exist if you over monetize them. But when you bring in a VP of sales for Lenny and a VP of growth and... You can't expect them to care as much about that long tail as you, right?

LennyI love your passion around this. So, what I'm hearing partly is you're a big fan of freemium, essentially, right? And the benefits of product-led growth where there's something you could just use indefinitely, or do you still think that's a trial where it needs to end at some point? Or is it just like, "No, freemium is great in a lot of cases."

Jason LemkinListen, I'm a big fan of long tails when they work. They don't always work for enterprise products. I'm a big fan of delivering more value than you take out for your customers. And I am a big fan overall of free, because, and I know you'll agree with me this, every founder figures this out at some point, free products are better software. Products that cannot offer a free edition cut corners because they don't have to be good at onboarding. The products that do not have a free edition have human beings that bridge the gap between buying and deployment. And that's okay at ServiceNow, and that's okay in certain products, but the best products invest the engineering cycles to have a free edition. Whether that's truly free, whether it's an extended free trial, whether it's a long tail or a medium tail, the amount of... All of your product is better if people can actually, if you have a free edition, all your customers benefit, even your enterprise customers benefit, they all benefit.

LennyThis idea of VP of free, I think technically it's probably the head of growth for a PLG company or the person leading the self-serve part of the business.

Jason LemkinBut even in the organizations I work with that have those structures, that person is focused on monetizing that tail. Who stands up for the 590,000 other readers of Lenny? Who's their champion?
Yeah.

LennySo, yeah.
Makes sense. Oh man, there's so many things I can go into and want to go into. I also want to let you go. So with that, is there anything else, Jason, that you wanted to share before we get to our very exciting lightning round? Anything you want to leave listeners with?

Jason LemkinI think just make this the year of the customer guys. And I really think that sales has been under so much pressure the last 18 months. Customer success has changed. Product teams have to step up. This is your time to do great things this year as product people. Be the voice of the customer. Be the VP of free, be the whatever. Be the champion. Stick your neck out. Work harder, folks. Work harder. The funnest part of anything in startups is working hard, but in product it's extra fun. By working harder, you have the more fun conversations. Find the delight in... The delight in product is making customers happy. It's not worth it otherwise. Otherwise, it's drudgery and it's endless PRDs and Gantt charts and mindless discussions. Make your customers happier this year, you will be happy. This is the year of product and we all get a pass for whatever bad deeds we did or mediocre deeds we did in 2023, get back and be the vanguard in your companies.

Startups need, and bigger companies, they need someone to inject energy again, in many cases. Energy has been lost. And it would be great if product can do it and say, "Listen, let's do something, even if we're not exactly sure how to get more leads, okay? Even if we're not exactly sure what to do, there's one thing under our control is the code we write and the product we ship. Let's do three great things this year. Let's just do them not good, great. Let's do three great." And what you'll find is the whole company will respond, including sales, including marketing, including... If we start shipping great thing. Few things inspire teams more than when you're shipping great products. So, be... If you weren't the leaders the last two years, if you were being forced to weaponize your customer base somehow ship three great things this year. That's my challenge. Ship three great things.

LennyI love this. This is the year of product, that might be the title of this podcast.

Jason LemkinYes.

LennyJason, we've reached our very exciting lightning round. I've got six questions for you. Are you ready?

Jason LemkinOkay. I'm worried about the first one, but go for it.

LennyThey're very non-surprising, because they're always the same. What are two or three books you've recommended most to other people?

Jason LemkinThat's the one I just want to take a pass on. I know they're the same. I read more than anybody else in the planet, but I wish I had those two great, great books that have changed my mind in the last 12 months, but hopefully I've added some value. But this one, I think I got to take a mulligan on it perfect answer.

LennyAcceptable answer. Is there a favorite movie or TV show that you really enjoy?

Jason LemkinOh, the Terminal List.

LennyThe Terminal List?

Jason LemkinThe Terminal List, yeah. I'm not into the Chris Pratt. I'm not into that goofy superhero movies he does, and I know people like it, but The Terminal List, it's pretty, it's I got it, it's written by this ex Navy SEAL that I think tech people don't read the... Everyone, but outside of tech reads this author, but Amazon did this thing with The Terminal List and I think the reason it gripped me, it's like this post, it's like a lot of tech is right now is we're trying to do the right things, but are we doing the right things? It's just confusing. So this one, I couldn't put down, The Terminal List. That was my favorite show. The other one, the one I liked that I couldn't believe. You want the second one? Even though as product people, Maverick, and I'll tell you why. This movie Maverick, okay, you wouldn't think I'd be a Maverick guy, but the quality of this product, it was so high.

And what's interesting, you remember Maverick was supposed to come out before COVID, right? And Tom Cruise said no. He's like, "This is such a good product, we're going to wait years for this thing to come out." I'm like, " I'm not going to like this. I mean, cocktail was pretty good, but I'm not going to..." But as a product, when... I've watched this movie three times from a product perspective and just like software, when something is done that well, no wasted calories, no... You see everything tied together. That's the kind of software we love, right? It just delights us when it works better than we expected. So, those are my two.

LennyYou also did all his own stunts, which I think is a good metaphor for the VP of product, maybe being involved in sales?

Jason LemkinActually do the work.

LennyYeah, exactly. Oh man, I'm stretching it. Okay, next question. You answered a few of these already, but do you have a favorite interview question that you like to ask when you're interviewing salespeople, especially?

Jason LemkinI answered it, but I'll bring it up again in case you do it again, is, "What do you want to do your first 14 days to head of product or head of sales? What do you want to do your first 14 days?" It's not a technical 30-day plan, you don't have to do 28 slides. It's what I call a Colombo question. Not that I really watch Colombo, but Colombo is this old detective on TV who, I don't know if you ever, he would ask these dumb questions, right? And then the murderer would thought Colombo was so dumb, but by the end of the episode he'd always incriminate himself because the question. So, when I interview, I always do Colombo questions. They're never tough ones, right? They're always nice. I don't know if I'm nice, I'm honest, but the interview . But Lenny, what would you do your first 14 days as VP of product here? And they don't want to visit customers. Don't hire them for either all sales or product. Just don't hire them.

LennyI've got the answer now. That's exactly what I was going to say. Next question, what is a favorite product that you have recently discovered that you really like?

Jason LemkinMy two aren't really amazing, but I'll answer them. I love this Opus Clip app for making clips from video. I know you have a whole team, so you probably don't need it, but I produce a lot. I mean, a lot of us do content marketing, right? Whoever does it. I produce a lot of content. I don't have enough time to do this. So, the only AI tool that I've found helpful so far is Opus Clip, which takes all of the incredible amount of YouTube content we have, force ranks it and turns it into 59 second clips. And I'm a case study on the website, I tried the earlier products. They were almost there, right? But it's not, is it as good as a clip team? Right? Is it? No.

But literally in 60 seconds, what's interesting is it can do something, I don't have time to, I could never make YouTube clips. I could never make Instagram shorts. I could never make... It just would never happen, right? It would never happen. And the fact that one product enables you to do something at a minimum viable quality you couldn't do before, I'm a super fan. It's pretty interesting. So, that's my favorite. And my other one is this one. This is the folding phone that's finally as good as a normal phone. See, there's The Terminal List that I've got folded up and it just works.

LennyThat's wild. .

Jason LemkinWeighs the same as an iPhone.

LennyWow.

Jason LemkinAnd so the reason it's cool is this has changed the way I do productivity. One Plus, it's the One Plus. One Plus, yeah, it's the first one that's the same form factor, same weight, same... So there's really no, there's no loss, right? And I can use my normal phone here like I'm using, it's a little funky, but it's the same... And then to be able to do content, to be able to check, to be able to do full email, full account, full everything like an iPad.

LennyWe see your Tesla where it's going, that gets parked. That's very cool. So, it's basically like an iPad plus a phone in one.

Jason LemkinYeah, I probably use this 50% of the time of the iPad.

LennyWow.

Jason LemkinSo, that's it. That is it. The other ones that-

LennyAnd that's an Android?

Jason Lemkin... Make sense to me. Yeah, it's a Android, yeah.

LennyAmazing. I had not seen that. That is extremely cool.

Jason LemkinVery cool.

LennyTwo more questions. Do you have a favorite life motto that you often come back to share with friends or family, find useful in work or in life?

Jason LemkinIt's, "Be kind." When I reflect on my career, right? Mistakes, I don't think I'm mean. I actually think I care more than most people on the planet. I like to think I've helped a lot of people, but it's not taking the time to be kind at times and not taking time to be kind when things don't work out. Not taking time to be kind when you leave a situation. Not taking time to be kind when maybe someone's done the wrong thing, right? Not taking time to be kind to a customer that leaves, right? I remember in the early days of Adobe Sign of EchoSign, we had a top tech customer, and I killed myself to close this customer, right? Famous, huge, huge tech company today. And then our champion changed, right? Champion changed is the big issue in software and product and came in and brought in DocuSign instead of us.

And man, I was just so mad. I just tore into this guy. This guy had actually had dinner at my house, right? And he actually never, he just did it because it was good for his own career, right? And I was so mad, but I broke the relationship forever, right? That's just one random example. And I just think there's so much advice to fire fast and to be relentless and do all these things, right? But you've interviewed so many people, Lenny, right? I mean so many great leaders. I haven't done what you've done, but I've talked to almost all the top CEOs in SaaS, okay? And they're kind. It doesn't mean that they're soft, they're not soft, okay? They make tough decisions every day, but they're kind. And so in this world where everyone feels like they're getting ripped off or they're not paid enough, or I want founder pay for founder work, this motto, really it's troubling.
Everyone is founder pay for founder... "You want me to work more than 30 hours, Lenny? I need 30% of the company. I need founder pay for founder work." It's like, I hear you. But you'll find that by being totally committed, going to 110% and also finding a way to be kind, that will endure across your whole career. So, I know it's... Because I think I'm good, but not always kind. It's how I challenge myself all the time. Be kinder in that conversation. And the big epiphany, we already talked about it, it shouldn't have taken me this long to realize that anytime an employee fails, it's your fault, be kind. You hired them. They never knew what they were getting themselves into. If the job's too hard, if they lack the skills, if there's not enough budget, if there's not enough people, if it requires too many hours to work, you should have known that. Not them. Be kind. Be kind to every single person on your team that doesn't work out. That's not just putting together an email spreadsheet and sending it out. Try, try harder. Be there for them. Be kind.

LennyBe kind. I love this. I know that you actually, your username on Twitter includes, "Be kind." In your actual-

Jason LemkinIt's a reminder.

LennyYeah.

Jason LemkinIt's a reminder.

LennySo, you really back this up. Amazing. Okay, final question. You're on a giant conference, SaaStr.

Jason LemkinYes.

LennyFirst of all, just talk about what it is so people know and explore it and check it out. But the actual question is what would surprise people most about running a conference like this? Things that they know, think about it goes into running a conference like this.

Jason LemkinAny business, no matter how weird it is, that's at scale, the best one in it, it's always interesting, I think for case studies, right? The best, pick anything, the best cup maker, whoever it is, whoever makes the best... This is not an interesting business, the Starbucks cup on its own, but the best person, I pretty much guarantee you there's a good story there, right? SaaStr is a community as well like you have. We started this really early in 2011, 2012 for B2B founders back when that seemed like a weird thing to do. Now it doesn't seem so weird. So, we built a lot of content and we started doing events and meetups. I never did a meetup. You do a lot of meetups, but when I did meetups, I'd never actually even been to one. So, I did meetups in 2012 and 2013, but 1,000 people came to the meetups.

That will make sense to you today, but a decade ago for B2B, it was pretty, people were like, "Why are all these people here? We thought there was six of us that cared about B2B." So, then we did a big event. We did a one-day SaaStr annual in 2015, and 3000 people came including the evening. And so we just kept going. So, we get about 10 to 12,000 people together a year. What that means is change. It's no longer novel. I'm not the only person producing B2B content anymore. I'm not the only founder that sold their company like in the old days. There's plenty much more successful founders and better, I certainly, I don't do very many podcasts, because I'm not a hundredth as good as you. I do one a quarter, for example.
But the events have become this meeting place for founders that have hit scale, that are somewhere between 1 million and 20 million. And especially folks that aren't in Silicon Valley, especially folks that aren't sitting in Hayes Valley or wherever, that don't have a community. And that surprised me in the beginning how many international folks would fly all the way to the Bay Area. I remember this founder came from Perth, Australia for the first afternoon. I'm like, "Thanks for coming, but this is a lot of work." He is like, "I didn't come for you. I came because there's no one like me in Perth." So, it's taken on a life of its own. There's a lot of learnings. I think, I didn't intend to do mass scale events. I intended to just do meetups, because I had a community like you do meetups. So, it was absolutely an accident. The learnings are, it's extremely expensive and it has this weird curve. Okay, that's this weird curve where, and this is more because I think actually all founders, all startups should be doing events for their own customers, at least steak dinners I've written about. You should get your customers, if you get your customers and prospects together, you sell more. Get your customers and... It does not need to be a million dollar or 10 million event. It can be Roots Chrises, it can be whatever. It does not even need to be fancy. Just get them together.

LennyIt has to be steak though.

Jason LemkinYeah, well, no, but steak does work. I mean, I'm not a big steak guy. It could be any, just something nice where they want to go. It, just where they want to go. Your customers will sell your prospects for you. Your customers will do the selling for you bring them together.

When you do it really small, it's cheap, because how much does that back room cost at the steakhouse, right? It's worth it if you get one big deal out of it, right? And then you graduate and then you'll do a meetup and you'll do it at someone's office. Some tech company, they'll give it to you for free, they have an extra office. That costs nothing, right? And then you're like, "Well, that went well. We got 100, 200 people came to Lenny's thing at Digital Ocean." And then you say, "I'm gonna do an event." And then you rent a theater, a disuse. And these theaters are actually kind of cheap because they're dark during the day. There's not a lot going on and a lot of... Not movie theaters but music. So, those are cheap. But then you're like, "Well, there's only one stage and it smells like beer."
So, then the next year you do a hotel and a hotel's pretty expensive. It's like half a million, 800,000 and I hated hotels. But you know what I learned from the business model? It's turnkey landing. So, your marketing manager can call up the Hilton in any city and in two weeks spool up some mediocre AV, some mediocre chicken wings and drinks, okay? And you and I don't like to go to the Hilton that much. The ballroom C, we don't like to go to events , but it turns out your customers don't care. They want to be together and talk about your app, right? And then if you do community like you do, you could probably charge a couple $100 for tickets and get some sponsors and bring in some revenue, right? But then after Hilton Ballroom B, it costs $2 million to turn the lights on.
And SaaStr annual... So, our Europa event in London's in early June, June fourth to fifth, please come if you want. That costs $2 million to turn the lights on in London. To turn the lights on in the Bay Area for 12,000 people in September in the Bay Area, which is the most expensive place, right? It's $10 million to turn the lights on.

LennyHoly shit.

Jason LemkinIt's $10 million to turn the lights on. Now, I'm being a little expansive in what I mean by turn the lights on, but this is what it's going to cost you. It's going to cost you about $1000 per attendee in the Bay Area or Las Vegas to have a mass scale event. Not smaller, not one day in Grand Ballroom B, but a multi-day event, right? The AV is 1.5 million. The food and beverage is 1.5 million. The tenting is $800,000. I can keep going. So, once you get to 20, 30, 40 million in revenue, quietly, there's public companies out there.

They have software like Margins at that scale, but before that, it's brutal, right? And when I started doing these events, I interviewed the head of it back before March 2020 when tech companies did their own events, they've pretty much given up, which is an interesting side topic. Big ones like big, not small ones, but big ones. Biden View, the head of events at everyone, right? At Twilio and Marketo and dah, dah. They all be like, "Well, how'd the event go?" It'd all be the same. Well, we brought in about 1.5 million revenue. " Oh, okay." "And we lost 2 million." Everyone lost 2 million. Every single one lost 2 million. And you could see in the financial state, even Zoom at that scale just announced how much money they lose at Zoomtopia. So, it's a terrible business. What I like to say is it has diseconomies of scale. The Lenny's little free meetup costs zero, right? And then the one at Cloudflare's office costs zero.
And the one at Hilton B maybe costs $200, but then it costs $1000 per person at scale, right? Even more like Moscone like in San Francisco is probably the most expensive. You're approaching $2,000 per person, because you have to buy about 15 to 20 million of hotel nights to do an event in Moscone, right? So I don't know if that's... We could, I mean it's a side topic, Lenny's side podcast for people that care. But this diseconomies of scale. But there are a handful of public companies that do Lions, Money 2020, Shoptalk, a few others that are at SaaStr scale. And they cobbled together these very profitable public companies. But they all got to do at least 20 to 30 million, because you've got to get over a 10. And it's intimidating to get over a $10 million net, right?
And so what it means is we have to spend 14 to 16 months each year planning for SaaStr annual because it's not that fun if you fall six or $8 million behind. That's what happened in March 2020. We were the first major event to be canceled by COVID in March 2020. The first one, RSA happened for security the week before then we got canceled. So, we lost $10 million in one day and it took a long time to dig out of that hole, Lenny, especially since we monetize nothing, it took a long time, but they're worth it.
I know you don't do traditional events, but you do do meetups in your community, and I know they're worth it. I know they're worth it. Bringing your customers together, bringing your community together, and we talked about this offline before we started. Second tier, third tier events I do not think are worth it because they do not attract the best people. It's just a fact. Most people, it turns out from our founders are our core ICP. They go to two events a year on average, two events a year, okay? And they'll do other steak dinners. So, if you go to one of the two that they're at, you just might bump into Jeff Lawson or Eric Juan or whoever the next one. They might be there. That might be one of their two, but they don't go to number three through 10. They don't go to these. So, my role in general is people wonder, should I go to events? Is it worth my time? It's a waste of time.
And I know you've thought about it. And the irony is, even though we produce events, I used to think that. I didn't want to do events, I just wanted to do meetups, right? I was shy, I just wanted to do meetups. But then I learned over time that the best events bring the best vendors, the best executives, the best everything together. So, pick the one or two best events in your industry. And even if you're antisocial, try to go to one or two a year, go along. It pays off. It pays off, but maybe don't bother with the rest, even if they're ski slopes or they're fun that the subscale, subscale just doesn't work for meeting and marketing to people. It just doesn't work.

LennyI said at the top of this podcast that there's a billion things that we could talk about, and I think that's exactly what happened. We can go in so many directions. And that alone was extremely interesting, because people want me to run a conference and I really don't. And I really enjoy the meetups that we have now. And we actually do have sponsors that cover drinks and food and things like that, and they're very chill, and I really love what happens at those things. But yes, this is really good information. Jason, I have two more questions for you that I ask everyone. I think we went through a couple of these things, but just real quick, where can folks find you if they want to reach out and maybe follow up on some of the stuff you talked about? And how can listeners be useful to you?

Jason LemkinIn general just go to this kooky, URL, SaaStr, saastr.com. That's a way to access a lot of what we're talking about. If they want to reach me to be transparent, I get a lot of impound, like I'm sure you do, to be honest, guys, it is hard to process the amount of inbound that folks get, right? But I'll give you an insider tip. I do see almost all of it. So, if you want to reach me, if you just want an hour of my time randomly, I'm sorry, honestly, I'm sorry, I don't have that hour of time, okay? But if you want to interact lightly, I mean, I'm on Twitter all most days @Jasonlk. I'm on LinkedIn a lot, just search for me, Jason Lemkin. LinkedIn's pretty cool. I have 260,000 followers. We have really good conversations. And I will tell you, if you have a question like you really need some help in your business or you want to do a pitch, if you send me the world's best email pitch, I will read a 100% of them.

Track it, put it in Mixmax, put it in HubSpot, put it... You'll see I'll open that email if the title's good. It doesn't mean I can respond. I'm sorry, no, Lenny can't respond, but realize it is going to be read. If you need a favor, like a help, if you ask the question super discreetly like, "Jason, here's the LinkedIn, I'm Lenny. I'm trying to hire this person. I'm at four millionaire doubling. Should I hire her?" There's a chance I'll look at that LinkedIn, I can tell you, or if it's one question, but if it's an hour or coffee, it isn't going to work, but it is going to get read. So, do that by email. Do it even by LinkedIn. I didn't used to read those LinkedIn emails, but if it's really good, I will read it and I probably respond to five or six of them a day.
I give to the extent that it's helpful, free answers, free advice. Not that I charge for anything, but make it good. Don't ask for coffee. So, many folks have written this, the most important people in the world read email. It's an open medium, right? And a subset of those folks actually read their social media. Even Elon Musk reads his, before he bought Twitter, he read it. You can access almost anyone in this industry. Just be super strategic about how you do it. Again, put yourself in your shoes. Would you answer this? Would you do this? But I would say half the stuff gets open to read. So, I know that's a rambly answer, but first, we talked about sales. You can reach anybody in the world via email. It's magical.

LennyI'm sorry for the many emails you might get from this podcast. That is actually really good advice. Resonates deeply with me as well. Jason, thank you so much for being here.

Jason LemkinThank you for all the time, Lenny. I'm a super fan. It's great to be here and let me know anything I can do to support you or your community going forward.

LennyI really appreciate that. And the same in reverse. Bye everyone. Thank you so much for listening. If you found this valuable, you can subscribe to the show on Apple Podcasts, Spotify, or your favorite podcast app. Also, please consider giving us a rating or leaving a review as that really helps other listeners find the podcast. You can find all past episodes or learn more about the show at Lenny's podcast.com. See you in the next episode.

Jason Lemkin99% 的创始人和销售都会犯同一个错：在 B2B 里，我们不是在“推销”，我们是在解决问题。SaaS 销售不是卖二手车，而是带客户开上一辆性能版 Model 3。它有竞争对手，你也许这周不一定买，但它确实很强。我的工作是帮你在今天就坐上这辆车：月末还有优惠，我已经花了四通电话回答你的问题，解释为什么超级充电网络比你家附近那个不好用的充电网络更靠谱。我甚至还帮你查过地图，确认你附近只有 Supercharger。SaaS 销售就是这样，因为我们卖的不是大宗商品。

Lenny今天的嘉宾是 Jason Lemkin。Jason 创建并运营了 SaaStr——全球最大的 SaaS 和 B2B 创始人社区。他每年还办两场大型大会：湾区场超过 1.5 万人，欧洲场超过 3000 位 SaaS 高管、创始人和创业者。做 SaaStr 之前，Jason 是 EchoSign 的联合创始人兼 CEO，把公司做到超过 1 亿 ARR，后来卖给 Adobe，并担任其 Web Services 业务副总裁。如果你在 Twitter 或 LinkedIn 关注 Jason，就知道他在 SaaS 增长方面有很多一线经验。

这次我们重点聊一个很多产品负责人最缺经验的能力：搭销售团队。我们会非常落地地聊：什么时候该招第一位销售、前一两位销售应该长什么样、为什么一开始最好招两位而不是一位、如何设计薪酬、如何面试、什么时候该招销售 VP、怎么避免销售团队快速流失和烧光现金。我们还会聊产品与销售怎么建立健康关系，比如如何回应销售提的功能需求、为什么产品负责人要深度参与销售流程、试用期应设多长、为什么应避免年付合同等。
Jason 还分享了不少办大会的经验，也很有意思。这期内容之所以很长，是因为我实在停不下来。希望这期“如何搭销售团队”的深度内容能帮到你。
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Jason，非常感谢你来做客，欢迎来到播客。

Jason Lemkin太兴奋了。算是“老粉第一次来电”那种感觉。

Lenny第一次做嘉宾。

Jason Lemkin对，第一次做嘉宾。谢谢你邀请我。

Lenny非常欢迎你。我一直觉得你迟早会来这档播客。你对 B2B 业务的很多环节都有洞察，但我想这次聚焦“销售团队搭建”会最有价值：从 0 到 1，怎么组建、怎么扩张、关键环节怎么做。可以吗？

Jason Lemkin太好了。这是个常青话题。工具会变、节奏会变，但创始人在搭销售团队时的困惑和恐惧，一直都在重复。

Lenny完全同意。对我来说销售一直像黑箱。我自己没做过销售，所以很想系统学习。先问个基础问题：是不是每家公司都需要销售团队？如果你是创始人，该怎么判断“我到底要不要 sales”？

Jason Lemkin如果你真的做出了极强的 self-serve 产品，你可以很晚才建销售团队，甚至长期不建。像 Slack、Canva 都曾经非常靠自助增长。Canva 到了 5 亿美元以上收入才真正大规模建销售；Slack 早期也是自助为主，但上市时大部分收入已经来自企业销售。也就是说，你可以做混合路径，不是非黑即白。

但最重要的是“诚实面对现实”。你前 10、15、20 个客户是怎么成交的，就很可能决定你后面 100、1000 个客户怎么成交。如果这些客户部署时需要你投入大量人力，需要回答安全、竞品、上线等问题，而你却因为不喜欢 sales 就强行走纯 PLG，你会失败。
很多产品型创始人会逃避这个现实。我投过一家公司，20 个月前收入 500 万美元、增速超过 100%。环境变难后，创始人因为“讨厌销售”把整个销售团队砍掉。现在收入掉到 100 万以内。客户其实很喜欢他们，但他们主动放弃了销售动作。类似案例我见过很多。
所以你得诚实：你现在到底靠什么成交。很多人会说“我们要找到自己的 niche”，但常常是市场先告诉你 niche 是什么。你要么顺势而为，要么因为觉得 sales 很“脏”而逃避，最后错过增长窗口。

Lenny你说“诚实”，具体是指要承认：你确实需要销售协助，才能持续成交？

Jason Lemkin对。诚实地看你前 10~20 个客户的真实成交路径。如果他们都可以无接触刷卡成交，那你今天就是自助基因，就去把增长、病毒循环这些能力做到极致。但如果他们说“我愿意付你 5000 美元/月，但你要帮我解决一个复杂问题”，那就不是纯 self-serve。

更常见的是“混合错觉”：一部分客户能小额自助，但成本很高；另一部分愿意高价购买，需要对接。很多不喜欢销售的创始人会盯着低价自助那批，回避高价值客户。我几乎没见过这种回避能走到长期成功。

Lenny我投过不少公司，早期都想纯 PLG，后来发现不行，最终还是转成 sales-led。

Jason Lemkin大多数公司最终都会是混合模式。很多创始人早期把它想成二选一，其实不是。

Jason Lemkin很多公司本质上都是混合模型。甚至 Mongo、Snowflake 这类公司也是：底层有免费或开源版本，中间层未必强，但高端企业销售很强。PLG / self-serve 和 sales-led 有很多组合方式。问题是很多创始人一开始就把它理解成“二选一”，其实不是。

Lenny所以核心不是“要不要销售团队”，而是“什么时候需要”。Canva 这个例子很夸张。

Jason Lemkin但他们现在也有销售团队了。

LennyNotion 好像也是到了 1000 万 ARR 左右才招第一个销售。那就引出下一个问题：什么信号意味着该招第一位销售了？

Jason Lemkin就算你讨厌销售、觉得它油腻，95% 的情况下，创始人也得自己拿下前 10 个客户。怎么做可以讲很多细节，但有个“捷径”：客户就是爱跟 CEO 聊。再加上创始人通常最懂产品和市场，所以你可能不擅长 cold outreach，也不擅长开场收尾，但你往往是 A+ 的“中段选手（middler）”。只要进入对话，你就能把问题讲透，这非常关键。

早期客户和创始人直聊，这个优势很大。你要练的是：把中段对话推进到下一步和收款。比如直接问：“要让你下周上线，我们还差什么？”你不用学那些油腻套路，但必须会把对话推到成交动作。

Lenny你说的 middler 是指：不一定最擅长开场和收口，但中间讲清价值很强？

Jason Lemkin对。很多销售一旦超出五六个标准问题就接不住了，比如数据库怎么跑、怎么减少幻觉、复杂场景怎么落地。早期销售经常需要创始人、售前工程师或产品负责人一起补位。创始人最大的优势是中段几乎不需要别人帮忙。你做新 CRM 时，在产品深水区你可能比 Salesforce 或 HubSpot 的绝大多数销售都更有说服力。

Lenny那回到执行层面：除了“先自己拿下前 10 单”，还有什么信号说明该招 sales 了？

Jason Lemkin当你有了这 10 个客户，并且 20% 以上时间都在做销售，就该加杠杆了。作为 CEO，销售和招聘这两件事各占 20%，基本是底线。超过这个阈值，你的日程会崩。此时要招人，而且一开始就要招两位，而不是一位，因为你需要做人类 A/B test。

我见过太多创始人第一批销售招错。最关键的一条：前两位销售必须是“你愿意从他手里买你自己产品的人”。当然还可以看客单价匹配、行业经验等，但这条是底层筛选。
你会面很多人：大多数准备不足，少数看起来“还行”，再少数是明显对的人。即便背景不完美，只要你真愿意从他那里买单，他大概率能跑出来。反过来，很多人简历很漂亮、术语很熟，但你自己都不信他能卖动你的产品。
早期线索太珍贵了。你给错人两个线索，公司可能错失一个季度。不要迷信 logo，不要只看简历。
我当年第一位销售并不是“完美履历”：之前创业公司离职，还住在兄弟车库里。但他对客户问题理解极深，能把我们产品价值讲得非常透。后来他连续拿下我们第一笔 5 位数、6 位数、7 位数 TCV 合同。你要找的是那个“真能卖你产品的人”，不是“最像标准答案的人”。
很多创始人忽略一点：早期最稀缺的是线索。你每月可能只有 3 条线索，给错人 2 条，基本就伤筋动骨。所以宁可多面，也别急着“将就招”。

Lenny这建议太实用了。那关于“级别”呢？很多公司会很早就招 VP of Sales。你建议前两位应该是什么层级？

Jason Lemkin两点。第一条是我讲了十多年的：至少先有两位销售稳定达标，再招 VP。大多数 VP 的职责是把“3 个人的小系统”扩成“300 人可复制系统”，不是从 0 帮你找 PMF。你要先有可复制脚本、可用线索，再扩编。

太早招 VP，本质是在要求一个人同时做四件事：找 PMF、当首位销售、当第二位销售、再搭规模化组织。几乎必败。
而且早期销售必须是“产品高手”。创业公司产品通常还不完善，但会有一个 10x 特性。优秀早期销售能把这个 10x 特性卖明白。很多流程型 VP 看不懂这件事，团队就会跑偏。
所以先把第一性问题跑通：你有没有两位能稳定打单的销售，然后再谈 VP。

Jason Lemkin很多创始人最致命的错误是：刚融到 400 万美元，就急着招 VP of Sales，觉得问题会自动解决。现实往往是 8 个月后 VP 走人，400 万里有 200 万已经烧掉了，因为他根本还没理解产品。要是只让我给这期听众留一句话：早期销售团队必须是“产品专家型销售”。等你规模化后可以更流程化，但早期不行。

我以前刚离开自己公司时，常去面 GitHub 那类公司的销售。我会问：“你有技术背景吗？写过软件吗？”很多人都没有，但他们仍然能卖好，因为 GitHub 已经成熟了，典型问题就那十来个，再配一个售前就能覆盖。但早期创业公司不是这个局面，所以你要找的是那种对产品理解很深、接近 product savant 的销售。把一个纯流程型 VP 丢进来，通常会失焦。
第二点我曾经纠结很久：招 VP 后，他要不要自己背 quota、亲自卖？我以前并不确定。

Lenny“背 quota”就是要自己关单？

Jason Lemkin对，不只是当老板。

Lenny有指标、要拿结果。

Jason Lemkin对。我过去犹豫的原因是：如果你是高速增长公司，要从 2 个销售扩到 6 个，目标是新增 400 万 bookings，每个销售配额 40 万，就要 10 个销售。VP 入职时只有 2 个，他必须 6 个月内再招 8 个。这个时候让他全职做个人贡献者，确实可能招不完人。

但过去 18-20 个月我看到的问题是：很多 VP 入职后根本不进入一线，不会卖产品，只想做管理。这非常普遍。
至于形式是全额背 quota、半额背 quota，还是大量陪访，都可以灵活；但你一定要让 VP 每周大量待在 deal 里。现在很多 VP 入职两三个月，几乎不在 deal 里。董事会上问“Airbnb 这个单怎么样”，他回答“我得问 John”，因为他压根没在现场。
我在另一家公司也遇到过类似情况。有位 VP 人很好，但入职 6 个月后，新签反而比之前更低。他很诚实，说最大问题是没时间学产品，而产品又比他上一份工作复杂很多。

Lenny这正是我期待的对话，太实操了。我试着总结一下：创始人先亲自拿下前 10 个客户；当销售占用你 20% 以上时间，就该加杠杆。再补一条我听过的：你需要已经形成一个可复制的销售过程，至少能讲清“我是怎么卖出去的”。这条对吗？

Jason Lemkin对。你若在这之前就招 VP，失败概率接近 100%。

Lenny也就是说，你可以先招前两位销售，然后在流程还不完美但已初步可复制时推进。

Jason Lemkin对。难点在于创始人必须先当一段时间“很粗糙的销售负责人”：亲自带人、一起下场、一起迭代。哪怕你不擅长销售，也得这么干，因为你依然会是个不错的 middler。

Lenny我再提几个关键点：第一，首批就招两位销售，不是一位；第二，可能要面 30 个人，20 个不行，8 个一般，2 个才是对的；第三，选“你愿意从他手里买你产品”的人，而且往往比较“怪才”，未必是传统销售背景。对吗？

Jason Lemkin我会补一条：如果你做 B2B，前两位销售最好有几年 B2B 销售经验，且具备足够成熟度。早期公司没时间 babysit，也没有完善 onboarding。理想情况下，最好和你的客单价区间接近，这样节奏更匹配。核心是：你要敢把宝贵线索交给他。

Lenny明白。然后是：当你准备从 3 扩到 300 时再招 VP；而且在当下环境下，VP 至少要在一段时间里亲自卖。

Jason Lemkin没错。关键不是形式，而是他是否愿意下场。说句直白的：你要的是“真的还想做销售的人”。过去三年我面了很多 VP，很多人其实已经不想卖了，他们只想管人。

2021 太热、2022 大幅回撤、2023 很硬，很多人被反复拉扯到倦怠。过去 12 个月我大概面了 50 个 VP，多数都不太想做销售。这就是我坚持“要背 bag”的原因：它能验证你还在乎这门手艺。
顶级销售当然爱钱，但不只爱钱。他们也爱这门 craft：打磨脚本、打竞争、找反制策略、放大 10x 特性、跟团队配合。只爱职位、不爱成交的人，不要招。
我面过一个履历非常漂亮的人，来自头部科技公司，还说能带 8 个人一起跳槽。听起来完美。我问他：“在今天的分布式环境里，我认为更要多见客户，你怎么看？”他说愿意见，但最远不去旧金山半岛，只在家附近。说白了，他已经不想卖了。
这种人现在非常多：简历和背书都很强，但销售意愿已经熄火。你最大的战略性误判，就是把他们招进来。

Lenny你是怎么识别的？你会直接问“你还想不想卖”吗？对于前两位销售和 VP，面试各有什么问题可以问？

Jason Lemkin有个我常用的“Colombo 问题”，VP of Sales 和 VP of Product 都适用：“你入职前 14 天准备做什么？”如果我听不到“去见客户”，我就直接放弃。真正优秀的 VP，前两周通常会说：“先别给我排内部会，我要先聊 20 个客户。”
优秀的 VP 不会把前两周花在 PRD 评审、内部流程会和空转讨论里，而是先离开办公室去见客户。销售 VP 也一样：第一天就该想怎么进一线电话、进真实机会单。

Jason Lemkin顶级 VP 前两周通常就一句话：“先别管我，我去见 20 个客户，回来再说。”他们不会沉迷内部会议和流程文档，而是先把一线认知补齐。销售侧也是同理：第一天就该进五通电话、进真实 deal。

如果你听到的是“第一个月先搭流程、先把 Salesforce 跑起来、先做 territory planning”，那基本就是危险信号。三个人的团队还在划南区东区西区，却不见客户，这种节奏会把公司拖死。
不是说流程不重要，而是很多人拿流程当挡箭牌，本质上是不想下场。这个问题不止销售，市场、产品、客户成功都一样。
我最近在 LinkedIn 收到一封很好的自荐信，对方说想来 SaaStr 做客户成功负责人，还写了很多改进建议。我回她：“很好，但你要接受前期得亲自和客户、赞助商沟通。”然后就没回复了。那已经是我最近 30 天收到最好的 inbound 之一。
我并不是想苛责谁，很多人确实被过去几年折腾得很疲惫，我理解。但作为创始人，你不能把这种“高履历、低意愿”的人招进来。
行业里充满了 burn-out。如果你在面试里听到一点点犬儒、抱怨，或者“我不想见客户”，尤其在 VP 岗位上（产品、销售、市场、客户成功都一样），基本就可以判断：他以后也不会愿意见客户。

Lenny但如果公司更成熟一点，这类“管理型 VP”是不是也可以？

Jason Lemkin在 5000 万、1 亿以上的某些业务段，确实流程比重会更高，我同意。但即便 Salesforce 在做上亿美元大单，销售领导也不可能只在家刷新仪表盘。Marc Benioff 到今天还在飞去见客户。

他去达沃斯不是去“打卡”，而是高密度见客户、潜在客户、合作伙伴。一天见几十个会面，这才是效率。30 多亿、300 多亿美元收入体量都如此，你怎么能在早期公司招一个“不见客户”的 VP？
所以请记住：如果你的公司还没到巨头体量，就别招那种“只会看报表”的人。

Lenny回到首批两位销售。除了“你愿不愿意从他手里买”，还有哪些面试问题最有效？

Jason Lemkin最朴素的一条：本质上还是 “sell me this pen”，但换成“sell me this app”。不是搞突然袭击，你可以放在二面，提前给准备时间。关键是看他会不会认真做功课并把你的产品讲清楚。

今天每个产品几乎都有官网 demo、YouTube 讲解、客户案例。让我震惊的是，从 SDR 到 VP，很多人到第五轮面试都没看过你的产品演示视频，连基础认知都没有。
销售不需要会写 webhook，也不需要会发 API key，但至少应该把产品讲到“官方 webinar 那个深度”。现实是 100 个人里 98 个做不到，他们只是批量点“Apply”然后发模板消息。
真正稀缺的是那 1~2 个会花时间研究、能把产品问题讲明白的人。即使不完美，也有核心把握。因为 B2B 销售的本质从来不是“卖东西”，而是“解问题”。2024 很多人卖不动，根源就是没在解决真实的大问题。
SaaS 销售不是“卖车技巧”，而是“帮你选对那辆最适合你的车”。你要诚实解释优缺点，回答所有问题，最后推动下一步。甚至最好的销售在不匹配时会主动说“我们现在不适合你，六个月后再来”，这反而更建立信任。
最强销售敢说“不”。他们知道什么时候该关单，什么时候不该。很多人把销售理解为对抗式交易，其实不是。软件如果做得好是有魔法感的，能真正解决问题。你不需要 boiler room 式话术去硬推。
只有在 2020 末到 2021 年初那段异常窗口里，产品才看起来“自动会卖”。那段时期也误导了很多团队。

Lenny我觉得这都能单独做一期节目了：怎么提高销售能力。我们之前和 April Dunford 聊过，也很强调你说的“先帮客户理解问题与市场，再讲你的方案”。

Jason Lemkin对，我很认同她。

Lenny那给大家一个可执行动作：这个 “sell me this app” 在流程里怎么做才好？是让候选人做一轮正式演示吗？

Jason Lemkin直到 2020 年之前，销售面试里做产品 pitch 几乎是标配。以前是线下带屏幕演示，现在 Zoom 也一样。关键是“真实做一遍”。后来市场太热，大家急着招人，参考背调、演示环节都被砍掉了，只要是“有呼吸的人”就先招进来。

这种做法短期看似高效，长期很伤公司。到今天很多团队还没把招聘流程恢复到 2020 年之前的基本纪律。
我看到 95% 的招聘都在跳过关键环节，尤其是背调。你不做背调、不做真实演示，就把最宝贵的时间和线索交出去，这在早期公司代价太高。

Jason Lemkin后来大家连“给我做个 demo”这一步都不做了，因为太怕候选人被 Gusto、Deel、Remote 之类公司抢走。节奏变成：这个 SDR 只有三周经验但拿了 50 个 offer，今天必须拍板。可一旦这种仓促招聘失败，不只是公司受损，对候选人也更糟。那位在 Cloudflare 事件里被推上风口浪尖的人，很多问题都值得展开聊，但本质上首先是招聘方的责任。先不谈她有没有关单，单就“招了人却没把她放在能成功的位置”这件事，就是组织的问题。你招的人失败了，责任在你，不在他。候选人永远不可能在短时间内做足全部尽调。

这个道理从基层到高层都成立。作为投资人和董事，我有时会刻意做最后一轮面试。创始人通常希望我帮忙“促成入职”，但我更想做的是反过来确认匹配度。比如我会对候选人说：“你已经拿到 offer 了。接下来我最不希望看到的是你三个月后离开。我们慢一点，把你心里的疑问都摊开聊，确保你进来后能成功也能开心。”
有时创始人会因为候选人因此放弃而对我不满。但我会说：你现在怪我，未来会感谢我。因为一旦 hire fail，100% 是招聘决策的问题。我自己也会因为有人入职后不给力而生气，但本质上，很多信号在招聘阶段就该看出来。
这也是为什么“sell me this app”一定要做：在你发 offer 前，必须让销售真实演示你的产品。给他时间准备、再看一遍 demo 都可以，不要把它搞成陷阱。把人当你希望被对待的方式去对待。但如果你跳过这一步，你其实既坑了公司，也坑了候选人。

Lenny我喜欢这个流程，因为它正好对应你最核心的筛选标准：“我愿不愿意从这个人手里买我的产品。”所以通常是你给他一个作业，让他回去准备后再来演示，对吧？

Jason Lemkin如果是成熟大公司里非常交易型的销售 VP，他们可能会在流程里很快让你“现场卖笔”，因为他们每周要面几十个人，没时间。但如果你是创始人，已经筛到最后一两位候选人，我建议你明确告诉对方：“这不是套路题。我只是要确认你进来后会成功。”然后让他认真做一次产品演示。

如果他不愿意做，那他就不是销售。另一个现实是：景气期里很多人进入 B2B 销售，其实并不具备我们理解的“销售基本功”。他们不会 outbound，不会打电话，只会接“我今天就要买”的 inbound 线索。那类人不是没价值，但不是所有阶段都适用。

Lenny销售里另一个黑箱是薪酬和配额。早期应该怎么定 comp 和 quota？底薪和提成怎么配？

Jason Lemkin几乎所有人一开始都会把这个问题想复杂。真正关键的只有一个：销售能不能带回比自己总收入更多的业务。早期尤其如此。

新销售入职前 3 个月，能做到“带回业务 = 自己 take-home”都算不错。我的早期做法是：前 3 个月，你拿你所成交金额的 100% 佣金（当然这不是长期可持续模式），核心是先让他快速上手、先跑起来。

Lenny这里是只给佣金，不给底薪吗？

Jason Lemkin不是。要给市场价。早期创始人常焦虑：“这个销售要 15 万 OTE，我自己才拿 6 万，怎么给？”我们拆开看：通常是 50/50，50% 底薪、50% 浮动。也就是底薪大概 7 万，按月摊其实是可控的现金投入。你不是一次性掏 15 万，你是在用几个月时间验证一个实验。如果连这笔验证成本都不愿意投，那你可能本来就不该做销售驱动。

第二，你要设计双赢模型。一个销售若 OTE 14 万，长期应当带回 4~5 倍收入：小客户段至少 3x，中端 4x，企业段 5x 往上。第一天不必达到，但方向必须是这个。如果他拿 15 万、带回 45 万甚至更多，在营销成本不过高的前提下，这应当让你高兴，而不是焦虑。
真正会出问题的是：一堆人不关单，同时营销获客成本又很高。那 payback 会全面失真。但如果你有稳定需求和能卖的人，这个数学是健康的。早期别一上来逼 5x，先让他第一季度做到 1x，把分打上去，先活下来。
所以别过度纠结把 OTE 从 15 万砍到 13 万这种事。关键不是省这 2 万，而是他到底能不能给你做出 60 万、70 万的新增。你甚至应该希望优秀销售赚更多，因为这通常意味着业务在增长。

Lenny我总结下：比如 7.5 万底薪 + 7.5 万奖金，前期先让他更容易赚到钱，别给太大压力；长期再把模型拉到 4~5 倍产出，对吗？

Jason Lemkin对，奖金部分来自销售结果。

Lenny那你会每月或每季度都调整一次 comp / quota 吗？

Jason Lemkin如果一开始设计得对，几年都不用大改。可以做小幅微调，但别频繁改。销售团队也要生活，你要保持竞争力，但核心约束不会变：他们必须带回比自己总收入更多的业务。

如果你不断改规则，本质是在给漏水的船贴胶带，最后只会更快烧现金。另一个相关点是：早期“少而精”远好于“多而弱”。
规模上来之后，capacity planning 当然重要。比如你要从 5000 万做到 1 亿，每人 50 万产能，那数学上就是要 100 个销售，这在大公司成立。但在早期，这是常见新手错误：我宁愿要 2 个各做 100 万的人，也不要 20 个每人只做 10 万的人。后者会把文化和士气都拖垮。
所以先把“高质量成交能力”做出来，再谈人数扩张。

Jason Lemkin早期你要做的，是把最好的线索集中给最能成交的人，同时逐步培养新人。线索必须优先喂给最强 closers。这样到了第 2、3、4 年，他们就会赚很多钱，有时甚至“看起来赚太多”。

我第一笔投资是 Pipedrive（后来卖了 15 亿美元）。当时是 SMB CRM，公司基本纯 self-serve，我帮他们放了第一位销售进去。三个月后，这位销售赚得比创始人还多，创始人非常不爽。我跟他们说：这恰恰是你们应该想要的结果。
他做法很简单：先把所有自助客户按 seat 数倒排，从“买过不止一个 seat 的客户”开始打电话。比如当年给 AOL 打电话：“你们现在有 20 个 seat，要不要扩到 100？”对方直接同意。多出来的 80 个 seat 是他实打实拓出来的，给他 20% 完全划算。

Lenny所以你的建议是：别因为销售赚很多钱而难受。

Jason Lemkin没错。只要薪酬结构设计正确，销售赚钱=公司赚钱=股权升值。

Lenny那“前期拿 100% 佣金”什么时候切回正常比例？

Jason Lemkin我建议最多一个季度。超过一个季度太“宽松”，中位绩效的人会赖在这个机制里，反而伤团队。更大的问题是 mis-hire。对创业公司来说，最关键的不是“招到谁”，而是“别招错人”。

招错销售很可惜，但更可惜的是让他在错误岗位待 6 个月。对他也不好。你应该尽快帮他找到更适合的位置。销售和其他职能比，成败二元性更强：同一个人可能在 A 环境顶尖，在 B 环境彻底失败。所以要早识别、早处理，因为线索太贵。
再给一个超高价值判断：尽量招“上份产品比你更难卖”的人。反过来，如果他上份产品更容易卖，来你这儿通常会灾难性失配。哪怕人很好，也很难补齐能力。
我第一个 SDR 是 Sam Blond（后来当过 Brex 的 CRO、再到 Founders Fund 做合伙人）。他之前在 Intacct 做 SDR。那时候把财务系统上云非常难卖，客户把财务当命根子，不信任云端。Sam 在那种高难环境打过仗，来我们这里就像“卸掉铅鞋”，迅速成了第一名。
他后来从 SDR 一路做到 SMB AE、Mid-Market AE、销售总监。我问他为什么跑得这么快，他说：“你们这个比 Intacct 容易多了。”这就是我要的迁移优势。
所以请特别警惕“上份产品更好卖”的候选人。`sell me this app` 能过滤一部分，但还不够。招聘时我们经常在让步，而不是在坚持最关键标准。

Lenny怎么判断“他上份产品更难卖”呢？有没有启发式？

Jason Lemkin几个信号。第一，技术复杂度更高要谨慎判断：有人能从业务流程销售切到卖复杂 API（面向 VP Eng / VP Product），但多数人切不过去。第二，更激烈竞争环境通常是加分。一个很好用的判断是：如果他在“行业第 4 名”公司也能打出成绩，而你是“行业第 2 名”，那往往是优质迁移。

另外看业务流程复杂度。很多人卖过“流程简单的 B2B 产品”，到了“集成多、流程重、变更成本高”的产品会直接崩盘。我投过一家公司（已超 2000 万收入）曾把自己简化成“某领域的 Gong”，结果请来的高阶销售只会重复这句话，客户追问 Zendesk 到 Salesforce 的深度流程怎么打通，他答不上来，60 万美元单子当场丢了。
所以不能只靠 slogan。尤其技术销售，面对 VP Engineering 时，他们不吃空话。

Lenny我第一次听到 B2D（business to developer）这个词。

Jason Lemkin对，面向开发者。

Lenny明白。那我们拉高看，销售组织继续扩张时，结构怎么演进？

Jason Lemkin简化讲就是“8 的法则”。销售组织几乎没有你想象中的效率红利，很多时候甚至是反效率。你做 sales-led 的话，1000 万、5000 万、1 亿收入阶段，销售人员都可能占公司一半。

因为渗透率越高，获客越难，很多上市公司的 CAC 甚至比早期公司更高。所以你得按结构扩：8 个 SDR 配 1 个经理，8 个 AE 配 1 个上层负责人；再往上也是类似。
过去有人把 SDR 管理跨度拉到 12，但现在很多团队又回到 8。大家宁可少一点 SDR，但每个对话质量更高。

Lenny所以就是：先有 VP Sales，再补 AE，然后补经理？

Jason Lemkin对，到点就要开始补管理层。

Lenny再往后继续按 8 的节奏扩？

Jason Lemkin是的。AE 到 8 个时，优秀 VP 通常已经在找两个 Director 了。

Lenny两个 Director？

Jason Lemkin对，可以按东西区拆，也可以按 commercial / enterprise 拆。一个成熟 VP 在到 8 个直管时，通常就会提前布局下面两层管理者。

Jason Lemkin……或者是两个 VP（如果他自己是 SVP）。现在行业里头衔通胀挺常见，但这件事我没那么在意。只要你真的下场做销售、做工作，叫什么 title 都可以。关键是规模到 8 人左右，你就得补管理层。

另一个关键点是：很多创始人会说“我很喜欢现在的销售负责人，但她是不是 stretch 了？”我的回答是，前期本来就应该是 stretch。95% 的公司，第一任 VP Sales 都应该是“够得着但要跳一跳”的人，通常之前是 Director / Senior Director，或者半步 VP。
反而你要警惕的是“已经当过三次 VP Sales 的老将”来做第一任。他们往往不愿意做早期那份脏活累活了。你需要一个 still hungry 的 stretch 人选，这对他个人成长、股权回报、职业跃迁都更匹配。
当然创始人会担心：Lenny 能走多远？他去年做得很好，但会不会扛不住？最简单的判断是：他能不能招到比自己更强的下一层管理者。只要能持续招到更强经理，销售负责人就能一直扩下去；招不到，组织一定会卡住。
这条在所有职能都成立，但销售里尤其明显。很多 stretch VP 最后“溺水”，不是因为他不行，而是他下面一直招不到靠谱经理，只能做被动内部提拔。内部提拔当然要做，我的经验是 50% 内提 + 50% 外招最健康。但如果你只能提拔“刚做两年销售的新人”当经理，组织很快会裂开。

Lenny（赞助口播已省略）

（赞助口播已省略）
我们常说 AE、SDR 这些术语，可能先帮大家快速定义一下：AE 到底是做什么的？

Jason Lemkin对新手来说最容易混淆的是两个词：`SDR`（Sales Development Representative）和 `AE`（Account Executive）。

Lenny好，展开讲讲。

Jason LemkinSDR 通常是入门岗位，很多是刚毕业，OTE 大致在 6-8 万美元（美国 SaaS 语境）。核心工作是“发邮件打电话换机会”，也会筛 inbound 线索，然后把可跟进的机会转给 AE。

SDR 是 opener，AE 是 closer。AE 更资深，负责推进并关单。美国市场 AE 的 OTE 大致可能在 9 万到 20 万美元，取决于你卖小单还是大单，通常也是 50/50（底薪+浮动）。
现在行业里有个常见误解：创始人希望 AE 是“全栈”——自己找名单、自己做 outbound、自己跑销售漏斗、自己关单。现实中这种人极少，除非在强管控的高绩效组织里被严格驱动。大多数 AE 还是希望拿到线索后专注关单，所以你需要 SDR 系统去持续补需求。
更现实一点说，很多创始人最多有精力带几个 AE，但很难亲自带 10 个刚毕业、需要小时级盯管理的 SDR。如果你真能把 SDR 团队带好，那是超级能力。

Lenny这个解释很清楚。那前两位销售，应该先招 AE 级别，对吧？

Jason Lemkin对，他们会兼做一些 SDR 工作，但最终一定会走向分工。

LennyAE 往上是什么？Director of Sales？

Jason Lemkin基本是这样。其实我一直觉得销售缺一条真正的“高级 IC 通道”。产品和工程都有，销售却很弱。理论上你可以从 AE 往更大客户走、赚更多钱，但缺少明确的“超级 AE”职业路径，这很可惜。

所以很多强销售被迫往管理走，哪怕他们本质上更适合做高产出 IC。这也导致一个常见错误：创始人把热门公司里最强 AE 直接拉来做 Head of Sales。那通常不成立，因为“顶级销售”不等于“顶级管理者”。

Lenny我想换个方向：聊聊产品和销售。很多听众是 PM 或创始人。产品团队到底该多深地参与销售？反过来，销售该多深地参与 roadmap？

Jason Lemkin在我见过最好的 B2B 组织里，至少 VP Product 都是深度参与销售的，真的很深度。我投过一家公司刚过 6000 万收入，他们最近跟潜在最大客户开会，VP Product 在场，最终救了这单。

原因是客户要的不是“整套产品”，而是拆开用其中一部分能力。AE 很难当场判断这种“结构性适配”；就算 VP Sales 知道，也未必有权限当场承诺：“明天先这样上线，90 天我们把 UI 调成你要的样子。”但真正掌握 roadmap 的 VP Product 可以。
到规模更大时，这能力更关键。CEO 不可能每个大单都在场。优秀公司里，CEO 和 VP Product 会分工拿关键客户；有些产品感很强的 VP Eng 也能承担这角色。过去有些 VP CS 也能做到，但这两年我看到他们更多退回流程岗，少了这种产品型前置能力。
PM 或 Director 能不能做到？最强的一批可以。中位数那批只盯像素细节的，就不该被放进关键 deal。你需要的是对全产品极其熟、能把看似不相关模块串起来、还能对大客户做承诺的人。这是 B2B 公司最强战略武器之一。

Lenny很多 PM 最痛苦的一点就是销售提需求。你怎么看优秀 SaaS 公司处理“销售需求进产品”的机制？

Jason Lemkin这件事其实没那么复杂。我们都说自己一天发 28 次版本，但用户并不能消化“每天 88 次更新”。用户真正能感知并吸收的，通常一年两次大版本、最多季度节奏。所以先按“用户节奏”来管，不要按“工程发布节奏”来管。

最实用做法：每个季度给 VP Sales 一个明确预算（story points、功能占比，怎么计都行）。给了预算以后，协作会立刻变清晰。因为销售每天都在变：周一说 HubSpot 最重要，周三变 SAP，下周又变 Salesforce。不是他们不真诚，而是大单压力会让组织被“尾巴摇狗”。
如果没有预算框架，组织会被拖垮。尤其在高压 deal 下，销售容易过度反应，而他们本来也不是产品优先级专家。
你应该明确说：“这是你的配额，没人拿走（除非 CEO 特批）。”当资源真正“有边界”，销售反而会做权衡，会开始想“也许这季度不做 HubSpot 也行”。
CEO 要看 5 年，产品要看 2 年，销售通常看 12 个月以内，这很正常。关键是让 VP Sales 在预算内做全年平衡。你每周都要对齐：本季度在做什么、下两季度计划什么、哪些还能改、哪些已经开工不该频繁打断。要保持客观机制，不要全靠情绪。
如果你太情绪化，组织一定会坏。你可以说：“我们这项集成已经做了 80%，你若要全停掉去抢一个 100 万美元单子，我们也能做，但请确认这真是你最想要的。”把销售当成每周固定 stakeholder，奇迹就会发生。可惜我在很多董事会还没看到这种节奏化协同。

Lenny那如果我是 PM，销售来找我说“这个单就差一个功能”，我该怎么回应，既不拍死，也让他理解？

Jason Lemkin先看你这个 PM 是否真有 roadmap 决策权。

Lenny假设有一定决策权，可以影响 roadmap。

Jason Lemkin我理解你的问题，但我要强调：你希望一线销售和中层 PM 多交流，这是对的；但不希望他们直接拍板，这是错的。最正确的回答通常是：“我会把这个需求带给我老板，请你也同步给你老板。”

产品和销售之间有张力，其实是健康信号。没张力，说明你 deal 不够多。但这份张力必须有结构，不然就会演变成长期互相怨恨。
所以一线可以建议，不该拍板。可以午饭聊、可以提出好点子、可以“我会用我的影响力去推动”，但最终决策必须上推。否则你会从一个冲突变成一百个冲突，组织很快失控。

Lenny也就是“你找你经理，我找我经理，上层来决策”。

Jason Lemkin对，而且 VP Sales 与 VP Product 必须每周有预算对齐会。这样双方都会倒逼各自团队先做一次内部排序，再把高质量输入向上汇总。

销售侧你会发现：白板强制排序之后，输出几乎每次都会变；产品侧也一样，至少拿出 10%-15% 时间复盘销售需求。很多“看起来很难”的需求，可能团队里有人一天就能做，或者两万美元外包下周就能交付。那就是高价值时刻。
但前提是：有平行机制、有节奏讨论。否则这份张力会把团队耗死。

Lenny另一个趋势是产品团队开始背 P&L、背收入目标。你怎么看？

Jason Lemkin大方向上，团队对年收入目标对齐是对的。你问的是不是“奖金和考核直接绑定收入”这件事？

Lenny更像是 KPI/OKR 直接要求“这次实验、这次发布要带来多少收入”。

Jason Lemkin这件事我还在观察，但有个过去 18 个月的教训很明显。CS 团队以前的核心目标是“客户成功”（留存、NRR、GRR）；去年很多公司把它改成“从存量客户榨更多收入”，结果伤了客户关系。

我就遇到过一家头部上市公司：我们原本每月 299 美元，结果被要求立刻预付 5 万美元，不然就关停。后来又撤回了这个要求。比要求本身更糟糕的是——它其实只是威胁。这就是把一个本不该武器化的职能武器化后的结果。
所以我理解要对齐收入，但我担心我们会后悔把太多团队都“收入武器化”。这对客户体验是有损的。

Jason Lemkin话虽如此，我也说个反面经验。不是说 Adobe 不好，我在 Adobe 当 VP 那会儿，产品团队有些时候在另一栋楼、相对隔离运作。体验很好，但这种“隔离式敏捷”对我来说并不成立。

最大问题是他们不跟客户说话。我的底层观点是：产品必须持续贴着客户。VP Product 应该拿着大量股权、也关心全年 bookings；但要不要把普通 PM 武器化，逼他们为每个实验功能直接背收入？我倾向谨慎。
因为你能做的实验本来就有限，每个实验都很贵。网上说一天发 100 个功能，但真正把扩展产品推向市场，成本和风险都很高，你必然在“做这个”和“放弃那个”之间取舍。
如果你对产品试错过度惩罚，组织会停滞。反而大公司在这点常比创业公司做得好：新项目失败，不会立刻把人干掉。不然没人愿意去做新项目。
我在大公司学到的一点是：在可控范围内允许失败，是有解放性的。创业公司失败成本太高，所以这更难，但仍然值得保留一点“可承受失败空间”。

Lenny我补充一下，我更多指 PLG 公司，因为增长主要来自产品。你的建议应该还是“别把收入压力压得过头”。

Jason Lemkin对。压过头就会走向 dark pattern。我妹以前在 Vistaprint，核心工作就是在结账页逼用户顺手买并不想买的加购项。她还会因为这个拿很高浮动。它确实有效，但不会带来高 NPS。

Lenny嗯，确实。

再举个相关但很糟糕的建议：很多 VC 会让你把月付改成年付。坦白说，这建议大多数时候都很差。

Jason Lemkin在表格里看，年付当然漂亮；但比表格更重要的是让客户按他们想要的方式付钱。你我这种个人购买者，通常就是想先月付试用；大公司偏好年付，多数是因为采购流程。为什么要强迫用户走他们不想走的路径？

站在产品视角，我会尽量给“以用户为中心前提下最长的试用期”。我在董事会上听到“给 SMB 强推年付”时都会追问：有证据证明这对客户更好吗？你自己买一个 19 美元/月的新工具，真的愿意立刻付 240 美元年费吗？大概率会直接流失。
所以要多复盘“为什么丢单”，而不只是复盘“怎么赢单”。销售文化里常常过度迷恋胜利故事，这会掩盖很多真实问题。PLG 也一样。2023 年很多公司在压力下做了不该做的事：涨价、砍试用、藏免费版。我愿意给那段时期一次“压力豁免”，但现在该回到客户中心了。
我还会问团队一句很扎心的话：你去年涨价 8%，那你给用户创造了 30% 的新增价值吗？过去很多公司是“几年后产品明显更强，再涨价”，这是合理的；但去年很多涨价只是“发封邮件通知更贵了”。所以不是不能涨，而是要“先赚到，再涨价”。
尽可能给长试用，并明确谁来当“VP of Free”。这件事本质上应该是创始人 + 产品一起扛。你不能指望销售团队天然在乎免费用户，也不能指望增长团队在奖金压力下优先照顾长尾免费人群。

Lenny我订阅用户接近 60 万，但显然不是每个人都会转化。

Jason Lemkin正是这个点。那 59 万“没付费但喜欢你”的人，是你生态的一部分。你若过度变现，社区就会被掏空。引入 VP Sales、VP Growth 后，他们天然更关注短期转化，不会像创始人一样保护长尾。

Lenny所以你的观点是：freemium 在很多场景里依然很有价值。

Jason Lemkin我支持“有效的长尾免费”。不是所有企业产品都适用，但整体上我支持“先给足价值，再拿走价值”。很多创始人最后都会发现：能做出免费版本的产品，往往反而是更好的软件。因为你被迫把 onboarding 做好，而不是靠人工填坑。

即便是企业客户，也会从“你拥有免费版能力”这件事里受益。问题在于：到底谁为免费用户发声？很多组织里所谓“自助负责人”其实主要任务仍是变现，不是真正守护免费体验。

Jason Lemkin对。增长团队把 1% 提到 1.1% 很重要，但不能把全部精力都用来硬推付费。到了一定规模，创始人和产品负责人必须亲自回答：谁是“VP of Free”。

Lenny今天信息量太大了。我最后想给你一个收束：在进入闪电问答前，还有什么想留给听众？

Jason Lemkin把今年变成“客户之年”。过去 18 个月销售压力很大、客户成功角色在变化，产品团队必须站出来，做客户代言人。多干点、敢担责、把客户满意当作核心乐趣。否则就只剩 endless PRD 和无意义会议。

不管是创业公司还是大公司，都需要重新注入能量。即便不确定该怎么拿更多 leads，至少有一件事在我们控制内：我们写的代码和发布的产品。我的挑战是：今年至少交付三件“伟大”的事情，不是“还行”的事情。你会看到整个公司都会被带动起来。

Lenny“这是产品之年”，我感觉这都可以做标题了。好，进入闪电问答。第一题：你最常推荐的两三本书？

Jason Lemkin这题我这次想跳过。我读很多，但过去 12 个月没遇到那种“必须立刻推荐”的两三本。希望前面内容已经有价值。

Lenny可以。那你最喜欢的电影或剧？

Jason Lemkin《The Terminal List》。

Lenny就是那部《终极名单》？

Jason Lemkin对，《The Terminal List》。我其实不太吃 Chris Pratt 那类“轻喜感超级英雄片”，但这部抓住我了。原著作者是前海豹突击队员，科技圈里读他的人反而少。它打动我的地方在于：很像当下科技行业的状态，我们都在努力做正确的事，但常常又不确定自己是否真的做对。

另一部是《壮志凌云：独行侠（Maverick）》。这片本来能更早上映，但 Tom Cruise 选择延后几年，因为他觉得这是一部值得等的“高质量产品”。我从产品视角看了三遍：几乎没有废镜头，结构极其完整。就像我们喜欢的软件一样，超出预期时会带来真正的愉悦。

Lenny他还亲自做特技，这是不是也像产品 VP 要亲自下场做销售？

Jason Lemkin就是这个意思，亲自做。

Lenny下个问题：你最常问销售候选人的面试题是什么？

Jason Lemkin还是那题：“你入职前 14 天会做什么？”不用给我 28 页 30-60-90 计划。我喜欢这种“Colombo 式问题”：看似简单，但会暴露本质。如果他前两周不打算见客户，那无论产品还是销售岗位，都别招。

Lenny下个问题：最近最喜欢的产品？

Jason Lemkin两个。第一个是 Opus Clip。我们做内容的人都知道，剪短视频很耗时。这个工具能把大量 YouTube 内容自动排序并裁成 59 秒短片。它当然还比不上专业剪辑团队，但它让“原本根本做不到的事情”变成“60 秒可完成”，这就足够有价值。

第二个是折叠屏手机（OnePlus）。终于做到跟正常手机差不多重量和手感。它几乎把“手机 + iPad”合并成一个设备，对我的生产力帮助很大。

Lenny太酷了，重量居然也接近 iPhone。

Jason Lemkin对，基本同级别。

Lenny倒数第二题：你最常回到的一句人生信条？

Jason Lemkin“Be kind（保持善意）。”回看职业生涯，我不觉得自己刻薄，但我确实在不少关键时刻不够善意。比如合作出问题时、关系结束时、客户流失时，我有时反应过激。

早年 EchoSign 有个头部客户，我拼命拿下，后来对方关键人变动，转去用 DocuSign。我当时太生气，直接把关系撕裂。那是我长期后悔的事。
现在行业里很多声音在强调“狠一点、快一点、压榨一点”，但我和很多顶级 CEO 打交道后发现，他们都很硬，但也都很善。善意不是软弱，而是更高阶的领导力。
我甚至把 “be kind” 写在社媒名里，提醒自己。尤其当员工失败时，我现在更相信第一责任在管理者。是你招的人，是你定义的岗位难度和支持条件。别只发一封离职邮件了事，尽量多做一点。

Lenny最后一题：SaaStr 这么大体量的大会，最让人意外的地方是什么？

Jason Lemkin先说背景：SaaStr 从 2011/2012 年开始做 B2B 创始人社区。最早我只是想办 meetup，甚至那时我自己都没怎么参加过 meetup。2012-2013 年我们办活动就来了上千人，2015 做首届一日年会来了 3000 人，后面就一路放大到每年 1-1.2 万人。

十年前 B2B 圈很小，大家会问“怎么突然这么多人关心这个”。今天环境完全不一样了。

Jason Lemkin后来这些活动慢慢变成了“已跨过 100 万到 2000 万阶段创始人”的连接场，尤其对不在硅谷的人更重要。早期最让我震惊的是，很多国际创始人会专门飞到湾区，只为找同类。有人从澳洲珀斯飞来，我说“太折腾了”，他说“我不是为你来，我是因为在珀斯找不到同路人”。

所以我一直说：创业公司至少要做小型线下活动。客户和潜客被放在一个房间里，销售会自然发生。根本不需要一上来做百万美元级活动，哪怕只是一次像样的晚餐都有效。

Lenny所以必须吃牛排吗？

Jason Lemkin不一定非牛排，但“一个大家愿意来的好地方”确实有帮助。你的客户会替你向潜客背书。

活动规模从小到大是条很奇怪的成本曲线：最小型很便宜；借办公室办 meetup 甚至免费；再往上租剧场也还可控；但到酒店会场后，成本突然台阶式上升。
酒店模型的优点是“可复制交付”：你的市场经理两周就能在任何城市拉起一场还过得去的活动。用户未必在意你觉得“Ballroom C 很土”，他们更在意能不能和同行一起聊业务。
但大规模活动极其贵。伦敦 Europa 级别，光“开灯”就要 200 万美元；湾区 1.2 万人级别，开灯大约 1000 万美元。

Lenny太夸张了。

Jason Lemkin是的，真的夸张。按人均算，湾区或拉斯维加斯这种多日大型会，基本 1000 美元/人起。光 AV、餐饮、搭建就非常重。做到 2000-4000 万营收之前，这生意都很痛苦。

我当年还专门去问各家头部科技公司的活动负责人，几乎是同一套答案：“收入 150 万，亏损 200 万。”Zoomtopia 这种级别也会亏。这行业有明显“规模不经济”特征。
小活动成本几乎为零；到中型可能 200 美元/人；上到超大规模就 1000 美元/人甚至更高。像 Moscone 这种场馆，算上酒店夜数，可能逼近 2000 美元/人。
这也是为什么我们每年要提前 14-16 个月规划 SaaStr Annual。2020 年 3 月我们是最早一批被疫情取消的大型会，一天直接亏 1000 万美元，后来花了很久才爬出来。
但我仍然认为“把客户和社区聚在一起”是值得的。问题在于：并不是所有活动都值得去。对创始人来说，一年平均就参加两场核心活动。你要去，就去行业里最好的 1-2 场，别把时间撒在第三梯队。
我以前也抗拒办大活动，只想做 meetup。但后来发现，顶级活动会把顶级客户、供应商和高管同时吸进来。哪怕你偏社恐，也建议每年去 1-2 场真正优质的，会有回报。

Lenny这段太有启发了。最后两个收尾问题：大家去哪找你？听众怎么帮到你？

Jason Lemkin先去 [SaaStr](https://www.saastr.com)。如果要联系我，可以 Twitter（@Jasonlk）或 LinkedIn 搜 Jason Lemkin。我收到的 inbound 非常多，没法给所有人完整时间，但我确实会看几乎全部高质量消息。

如果你想提高回复概率，别上来就约咖啡 1 小时。请给一个“非常具体、可快速回复”的问题，比如“我在 400 万 ARR 翻倍阶段，这个候选人该不该招？”这类我很可能会看、甚至回。
本质是：最重要的人通常都看邮件，很多人也看社媒私信。关键是你要替对方着想，发一条“值得被回复”的消息。

Lenny希望听完这期别把你邮箱挤爆。感谢你今天来聊。

Jason Lemkin谢谢邀请。很高兴来，后续有我能帮的随时说。

Lenny非常感谢，你这边也一样。大家拜拜，感谢收听。如果你觉得这期有帮助，欢迎在 Apple Podcasts、Spotify 或你常用的播客应用订阅，也欢迎打分和评论，这会帮助更多人发现这档节目。往期内容和更多信息可在 Lenny’s Podcast 官网查看。我们下期见。