'$1M to $10M: The enterprise sales playbook with Jen Abel'

Jen AbelYou need to vision cast, you need to sell to a gap, don't sell to a problem. When you're selling to a leader, you need to be selling an opportunity. The market doesn't want to be sold to, they want to buy.

Lenny RachitskyMost founders would rather get 10, 10K deals than lose nine and get one 100K deal.

Jen AbelIn the very early days, people will discount till the cows come home because they think that's the way to get a deal done. The best clients are not going to do that to you. If they're sitting there nickel-and-diming you, they're not fully bought in on what you're selling them.

Lenny RachitskyIt might be giving you a false sense of success and product market fit.

Jen AbelAs soon as you become a comparison, as soon as you become one of three that they're testing out, you've already sort of lost. It's all about differentiation. Here's what you will be able to do tomorrow because of how we're going to serve you today.

Lenny RachitskySomething else that you talk about is that enterprise sales is very creative.

Jen AbelIt's more of an art. It's all about deal crafting. It is a relationship you're building with someone. If they know they can call on you, people will turn over rocks for you. I have a client at a Fortune 10 company where I was like, "It's so important we get the deal done this year. Is that possible?" And she's like, "It's a tall order, but if it's going to help you, let's do it." These are how enterprise deals gets done. It's relationships.

Lenny RachitskyWhat's kind of like the state of the art on go-to-market outbound tooling?

Jen AbelI don't use a tool. The thing about AI tools is they're all pulling from the same databases. I want to email someone not in the database that's getting hit by a million folks. I want to take a back door in, not the front door where everyone else is trick or treating.

Lenny RachitskyToday, my guest is Jen Abel, co-founder of JJELLYFISH where she and her team help early stage founders learn how to sell and now GM of Enterprise at State Affairs. If you want to become better at selling your product, this episode is going to blow your mind and make you so much better in every way. This is the second time Jen's been on the podcast. Our first conversation was focused around getting from zero to 1 million ARR, essentially founder led sales.

This conversation is part two going from around one million in ARR to around 10 million. This is the most tactical and in the weeds discussion you will find anywhere for free on how to actually become more effective at selling to enterprises. I'm so excited for you to listen to this conversation. If you enjoy this podcast, don't forget to subscribe and followed in your favorite podcasting app or YouTube, it helps tremendously.
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Jen AbelLenny, it's starting to feel familiar and I like it.

Lenny RachitskyI should have said welcome back to the podcast. So I actually shared on Twitter that you're coming back and I had so many people ask so many questions. Clearly, there is a lot of confusion and a lot of need for learning how to get better at the stuff, we're going to talk about sales, enterprise sales to frame the discussion, our first chat, which we're going to point people to if they want to start there, we focused on founder-led sales, which is essentially the beginning phases of a startup, kind of going from zero to about 100 million ARR.

This discussion is on the next phase, which is going from about a million ARR to about 10 million ARR in enterprise sales, not like PLG or anything like that. You have a bunch of really strong and counter intuitive opinions and piece of advice on how to be successful at this. So I'm just going to go through a bunch of these things. We'll see where it goes. Before we get into the first one, is there anything broadly, I don't know, is there anything broadly you want to share? Anything you want to say before we dive in?

Jen AbelNo, let's dive right in.

Lenny RachitskyOkay. Okay, so the first thing that I haven't heard anyone talk about before is this point that you often make that the mid-market does not exist. People often hear about enterprise companies. There's obviously SMBs and startups. There's also people just, "Oh, I'm going to go after the mid-market." Somewhere between. You don't think that's real? Talk about your experience there, what people should know.

Jen AbelIt's fascinating because if you ask someone to describe the mid-market, actually, if you ask someone to describe the enterprise, every single person has a different answer. It's either based off of revenue, it's either based off of market cap, it's based off of employee size, and I think a lot of people can get lost because selling to a hundred person organization is a radically different game than selling to a thousand person organization and there's no hybrid approach.

So the best way to think about it is you have small business which typically can be really powered by marketing, and then you have enterprise, which is typically going to be sales led. If you bucket them into these two very specific silos, it makes it much, much easier to understand what game you're playing. Now, when we talk about mid-market, I usually will say, "Are we talking about the upper end of small business or are we talking about the lower end of enterprise?"
And most people are usually saying the lower end of enterprise. And I say, "Great, know you're playing the enterprise game. Know the type of people you need to hire, the type of ACV they need because it makes it a lot easier than trying to have this middle ground that catches everything that doesn't distinctly define SMB and enterprise." So I say the mid-market doesn't exist because what is a mid-market hire? It's either low end enterprise or upper end SMB, and if you bleed those two games you're going to lose. They're so distinctly different. So that's kind of my theory on it.

Lenny RachitskyYou have this chart that you shared with me that will link people to where you kind of show the number of companies within each of these segments and there's basically nobody in this kind of middle segment, talk about that a bit.

Jen AbelThat's right, and just like the power laws, if you look at the Fortune 1,000 and then the lower end enterprise from there, it trails off so fast. Power laws totally exist in these large corporations and we can't be treating everyone the same.

Lenny RachitskyThis begs the question, where do you suggest companies start? There's obviously startups classically are just like innovators, move fast, can make quick decisions, enterprises have all the money. Usually the advice I hear is just don't go after the fancy companies to start because they take a long time. You don't want to screw it up. What's your advice on where to start for most companies?

Jen AbelThe exact opposite. Early adopters are those logos because they have to continue to stay at the number one spot. So they'll take tons of swings to continue to stay in the ... Staying in the number one spot is the hardest part. So those number one logos are like if you can give me just a slight bit of alpha, just a tiny bit, that's where I get promoted, that's where I get the pat on the back because we are the world's leader in our industry and we cannot be disrupted there.

So there's this running joke where not a running joke, there's this running statement where a lot of VCs will say, "Don't go after tier one logos, go learn down market." Or, "o learn from logos that don't necessarily carry a lot of weight." The ones that carry all the weight are the ones that are willing to take a shot and want to help, right? Because they also want to be, they also want to be able to dictate the roadmap.
Now it's the founder's job to decide what can be done and what shouldn't be done, but their voice takes you a $100,000 deal into a million dollar deal in a very short period of time. It will literally guide you there. So when someone says, "Hey, go after startups, such as short sales cycle." Yeah, that makes sense. I totally get that. It's very easy to define the decision maker.
It's very easy, you don't have to go through procurement, but in the age of AI where it's all about sucking the oxygen out of the room and winning the deal and getting your foot in the door as quickly as humanly possible before someone else tries to take that, you want to get to the enterprise as fast as humanly possible.

Lenny RachitskyJust so folks understand what we're talking about here, when you say tier one, what's a good way to think about what tier one is?

Jen AbelTier one is like your Walmarts, your McDonald's, your NVIDIAs, your Tesla, your ExxonMobil, your UnitedHealthcare, the logos that are the leader in their space, their job is to stay in the number one spot.

Lenny RachitskyWow. Your advice is because this is very counterintuitive. This is exactly what you're here not to do. Your advice is go after the Chevrons and the Mobils and the Walmarts as a startup.

Jen AbelBecause if you can get them, that's all the proof you need.

Lenny RachitskyHow do you approach finding someone? Let's just get tactical there. Just like say you're going after Walmart. I know this is not a five-second answer, but just how would someone approach finding someone at Walmart to sell to?

Jen AbelFirst of all, make sure the founder is involved, right? Everyone loves talking to a founder, so we'll start with let's get the founder involved as fast as human possible. The second is you need to vision cast, you need to sell to a gap, don't sell to a problem. There's a very big difference between problem selling and gap selling. Problem selling is highly specific, more technical than not, and it's the way that every salesperson is going to go about it, find the problem and anchor to it.

When you're selling to a leader, you need to be vision casting and you need to be selling an opportunity which is they are here, here's where we can take you. You know that image where it's like Mario or Mario, and then there's the mushroom and then there's Mario on blast, and everyone is like, "Don't sell the mushroom, sell Mario on blast." Well, that's exactly what it's saying.
It's about selling the opportunity. That's what gets the tier one logos excited and that is the best thing for a founder to sell, selling the vision versus the problem, and also it's what gets them to want to take a swing. Who wants to take a swing because you can do some small problem? They're not going to go to bath for that.

Lenny RachitskyWhat's an example of a vision cast in a company you've worked with just to make this real? What does it look like when you've done a great job?

Jen AbelWe have an ability to deliver alpha, meaning, we have information, we have data, we have a way of working that no one else can do or is going to unlock a new way of thinking for you or an ability to deliver to a customer or an ability to solve a problem. Right now, you have an ability to access this level of information. I have an opportunity through our resources or through this gated data, we have access to get you much further upstream so that you can get information faster sooner. It's kind of like the high-frequency trading that one second, that one second. They didn't do much. They didn't sell, "Oh, we're doing fiber cable connectivity. We're giving you one second of alpha before everyone else." It's more of that ability and that's not problem-selling, that's opportunity selling.

Lenny RachitskyI like this phrasing of just giving them alpha, that's such a simple way to imagine what this should feel like. We'll link to that image you're talking about with the Mario and-

Jen AbelYou know that image?

Lenny RachitskyYeah, the person that made that image originally is Kathy Sierra, if you remember her, do you remember? So there's this person, Kathy Sierra, she's from back in the day. This was a big, I don't know, lesson she taught is you want to not sell your people on a feature or a product. You want to sell them on them becoming a superhero.

Jen AbelYeah, that's right.

Lenny RachitskyThey are now a superhero because of the thing you've built for them. And so the vision here is here's how you become a superhero. Here's how this alpha will help you become more successful.

Jen AbelAnd that's why founders are so good at selling because they naturally go to vision selling and vision casting versus a typical trained salesperson is find the problem, ask these questions and it just kills the vibe. It just feels like you're talking to a salesperson, right?

It's like, "What's your script? And it's like that's not vision selling, that's like playbook selling." And in the age of AI where a lot of it is Alpha, it's about speed, it's about getting access to information, it's about training data, and look at how the market is reacting to it. It's all opportunity and it's all about the alpha.

Lenny RachitskySo just to make this more concrete for people, Sam, like sales person at Cursor, what would be an example of vision casting? The obvious idea there is your team will be more productive, you'll get more done faster than everybody else. Is that a big enough vision to cast?

Jen AbelI think it may be more of you'll be able to actually hire the 10X engineers that you don't necessarily have access to because they want to be able to use this type of tool. It's about letting them get differentiated talent or that's probably more of what I would anchor to of this is the 10X engineers use cursor. You don't, do you want access to 10X engineers?

Lenny RachitskyThey won't even join your company if you're not using Cursor.

Jen AbelYeah, yeah. Think about it. So many people are so specific about what they're able to, I think especially technical folks, I'm not a technical person, but I would imagine that they're not going to go to, they don't like to go to these corporations because they're forced to use some incumbent tools.

Lenny RachitskyGoing back to going after these larger companies, I asked your colleague, Justin, what he sees you do that most impacts the success that teams have with their sales process. And there's a bunch of I'm going to touch on, but one is most founders are insecure about asking for large ACVs for charging, or the way he put it is most founders would rather get 10 10K deals than lose nine and get one 100K deal. Talk about your advice there and what you see.

Jen AbelThere are in the very early days is people will discount till the cows come home because they think that's the way to get a deal done. The best clients are not going to do that to you because that's like a qualification criteria, which is like if they're sitting there nickel-and-diming you being like, "No, I don't believe it's worth this. I don't believe it's worth that." They're not fully bought in on what you're selling them.

So when I say I'd rather get $100,000 deal than $10,000 deals, I'd rather have one rock star client that's going to help me figure out the next stage of where this is going than 10 or maybe five that are a good fit, five that are not, and I still have to serve those five that are not a good fit, and that's going to distract me. So this is why I love enterprise sales is they're not going to do the hard work of bringing you in if it's not critical or if it's not, when I say critical, it's going to impact them in a way that they're going to make it successful, that's what I love about enterprise sales.
They have the resources to ensure that it gets implemented because most in today's day and age, if people are not using the tool, you just get rid of the tool. So they're going to want to make sure whatever they bring in, what they go to bat for, remember, they go to bat once every two years, maybe once every three years. You've got to make it feel incredible. You've got to make it feel like they're going to be a superhero going back to it.
Otherwise, what's the point? Because the way enterprises are structured is it is designed today to make it hard to buy because they want to make sure whatever you're bringing in, you really, really want it gets rid of the mediocre. I think this would be good and it gets to this is going to change the way we work. It's going to impact our ability to capture some form of alpha, however you want to define that for them and it's sticky because of that.

Lenny RachitskySo your advice here broadly is don't pay attention to the smaller 10K-ish kind of opportunities for a bunch of reasons. One is it might be giving you a false sense of success in product market fit. Two, those companies are maybe not as innovative and won't lead you in the right direction. Three are probably discounts just like your product than your pricing just gets thrown off.

Jen AbelYep, and also you don't really get taken seriously for 10K. You get way more taken seriously for a 100Ks, it's much harder to get a 100K deal done and an executive use needs to be involved. I'd much rather have an executive sign-off on something and spend two more months getting the deal done because you know that they are bought in, you can now ensure what kind of value do they want to unlock and maybe you have an opportunity to turn them into a user, which to me, in today's day and age, with our generation being the ones that are now the executives at these corporations, this is native to them.

Lenny RachitskyWho is this true for? Is the advice here basically, if you're trying to build a successful B2B company, everybody should be aiming towards these a 100K sort of deals? Is there a world where you can be successful with 10Ks for a long time?

Jen AbelIf you have a super high win rate in a massive market, because all you have to do is reverse engineer the math. If you need to generate a hundred million dollars in revenue, how many 10K deals do you need? And the expansion on a 10K deal is in parallel to that. Where can you go? 10 to 15? That's a 50% growth, much easier to go to a 100K to 500K because they want more bodies or they want more value out of you.

For an enterprise, they'd love to get more out of an existing customer. You're already trusted. So it's also about the type of company you are. If you're venture-backed, you can't be selling $10,000 deals to the enterprise, you'll get killed, or you've already lost the game because you're playing a small business game in the wrong sector.

Lenny RachitskyHave you seen startups you've worked with succeed in that 10K, 20K bucket or is it really, really rare?

Jen AbelIf they're going after the enterprise?

Lenny RachitskyYeah.

Jen AbelYes, if it's the first three months and then after three months, it turns into a 50K and then a 100K and it ramps up quickly. Sure, that makes sense. You got your foot in the door and you can expand it exponentially in a healthy manner. I think that that's fine. $10,000 a year, then going to 12, then going to 15, the math will break.

Lenny RachitskyThis is great. I feel like most founders to this are like, "No, no, we're kind of in that exception we'll be all right. 10K, we'll do 20K. That's crazy to consider 100K."

Jen AbelYeah, the math will break. And also, a really good salesperson, you're commissioned on a 10K deal, they're not going to get a great salesperson. They're going to want to be anchored to how can I sell a $250,000 deal? How can I sell a half a million dollar deal? That's the type of person you want.

Lenny RachitskyAnd a big part of this is this is a good lens to force you to build the product that you can sell for 100K, 500K.

Jen AbelYeah, absolutely. And again, this is about playing that enterprise game. If you're trying to sell, if you're a small business, if you're in the small business place and an enterprise company comes to you and is like, "I like this." Ensure that you structure it for an enterprise. Don't play the small business team with an enterprise company.

Lenny RachitskyTalk more about that. What does that mean?

Jen AbelLet's say you're PLG, and a big company like Walmart comes to and is like, "Hey, can we get access for three of our users?" And they're like, "This is so exciting." And then they sell them the small business pricing for three users to Walmart. Very, very hard now to go from those three users that you just priced them at in a small business way, turn that into 100K because now it's documented what they're actually paying for this.

So you're stuck. You've kind of anchored yourself to this price. Not to mention how are you going to unlock the executive high level value so that you can get that senior executive to buy in and stamp this as well. Otherwise, it's just going to be throwing it on the credit card. But again, you've just ruined your enterprise game because you're anchoring to a small business price.
So this is why when you bleed these two games, it's very, very, very dangerous because these are really smart companies. They're going to say, "Well, wait a second, I just paid $9,000 last year and now you want to charge me $90,000. Well, what's the step change in value? What's the 10X value I'm now getting?" That's super hard to prove.

Lenny RachitskySo the tip here is your initial price will really screw you if you get it wrong. And so obviously we're not going to give people the answer on their pricing strategy fully, but just is the advice just charged more or what would you recommend?

Jen AbelIt is enterprise companies are very used to a land, when I say the first initial contract, somewhat between 75K and 150K, very used to that. In fact, that's probably where you want to start because you also want to understand where can you grow from this. Start contained, don't say 150K and sell the farm. Say, "It's 150K, here's who gets access, here's the value we're going to deliver and here's where we're going over time." You also want them to know, "Here's what we plan to do roughly in year two, year three."

I know it's hard to look that far out, but plant the seed with them in terms of where this is going. If you come in at $10,000, even if they want to bring you in and want to spend 100K with you, they have to be able to defend that and now they see a $10,000, it can get really messy, especially because a lot of them are using AI now to understand contracts. So they're going to quickly say, "Oh wait, you spent a thousand dollars with Lenny and now Lenny is asking you for a 100K. Great. Just help me understand why or defend it."

Lenny RachitskyI could totally see ChatGPT being like, "This is interesting."

Jen AbelYeah, exactly.

Lenny RachitskyIt used to be 1K, now it's a 100K. What might be going on here?

Jen AbelTotally. The people don't realize how, again, know the game you're playing and don't be sloppy about it.

Lenny RachitskySo your advice here is really interesting. There's the land to expand. Expand is very important, but the landing may screw your expanding because it sets the wrong reference point.

Jen Abel1,000%. That's exactly right. You said it better than I did.

Lenny RachitskyAnd so you may see in theory if you land a 10K go to 100K, that's an amazing NRR, everyone's going to be really impressed. But you're saying people won't buy into that. It's going to feel absurd and wrong.

Jen AbelUnless it's defendable. All it needs to be is defendable. But who can really defend? That's very hard to defend a 10X. 10X jump, they're going to want to see 15X value.

Lenny RachitskyLet's talk about design partners.

Jen AbelOh yeah.

Lenny RachitskyThis is something most founders try to do. They find a few folks to work with, to help them build the thing. What's your advice on when to start finding design partners? How to find design partners, what a good relationship looks like?

Jen AbelDesign partners are incredible. They're the hardest logos to upsell, meaning go from design partner to full rollout customer. So don't expect these people to be your million dollar pipeline. Expect these people to be the guide, to help you understand, maybe design partners could be a technology company in the Fortune 1,000.

So they're used to experimenting. They're used to technology, they're used to, they were once a startup, so they get it. Those make really good design partners. Most of the design partners that I've closed are usually technology based. They get it and they also are excited about advancing the org and also giving the team an ability to have that startup feel.
So if you're a large massive corporation like Stripe. Stripe doesn't get that startup vibe as much like that 50 person startup vibe, but this can be a gift to give them that lens and give them that voice and give them that excitement that they don't get as a larger company. But those are great types of logos to be early design partners because one, they want to make sure they continue to stay on the cutting edge, but two is they are, to try and build something without that guidance is really, really, really hard because they're not using it.
So you need that user feedback and you also need to tie that to the executive value. It's actually a lot, it's very hard to do, but if you can come out of it and upsell a design partner to a full rollout customer, such a huge win for the market for you, for your team, and also for your investors because it's the hardest customer to actually truly convert.
They've been it when it was messy, they usually got a low price point. But if you again frame it, say, "Listen, I would love for you to be a design partner. I want a little skin in the game to get you to point it. Here's where we want to go and you'll get a discount because you were in the beginning, but I'm setting the framing. Here's where we want to go with pricing. Here's where we are today. You'll always have 30% concession in perpetuity because you are there with us on day one."
So again, it's not about asking for $10,000 and then not expecting that design partner to upsell and keep it flat because there's no growth there. It's a flat. It's about getting that early design partner, set the framing, own the framing and let them know where you're going. Again, a $100,000 to these large logos if they want it, it's very easy for them to get it in.

Lenny RachitskyThere's this really interesting underlying piece of advice of finding a company that pulls you in the direction that leads to success. A company that's kind of a visionary. There's the obvious companies that everyone is always trying to get these days, OpenAI and Anthropic and Stripe I think is one. And any advice for just picking the right early? What are signs that this is a company that will point you in the right direction?

Jen AbelI think they have to be part of a logo that is deemed startup-friendly or in that world, and then I think it's the person, is this person excited to give feedback? Does this person buy in to where we're going? Do they see this world differently like us? Are they in lockstep with the founder vision?

Are they excited to use a tool that's janky? Because it is janky in the beginning, but they know that where this can go can be incredible. So I think it's really about the person and making sure that they're aligned for what they're getting into, and I think a lot of salespeople oversell it. I think that's a common thing that happens and that leads to churn, that leads to frustration, that leads to sometimes just canceling the contract.

Lenny RachitskyThey oversell the initial kind of design partners phase over the product.

Jen AbelThey sell everything. Yeah, design partner, even full rollout, and it's so, so important to tell them, "Here's where we are today. Here's what we cannot do." Which is just as important. It builds trust. "Here's what we will allow you to do in the next six months. Do you want to be on this journey with us? And it's really ugly right now." Right? "Barely anything exists, but we would love your voice to be a part of it."

Lenny RachitskyOne of the biggest fears I think founders have is having a company pull, basically build just for their use case and then it ends up not being used by a lot of people. And so how far do you go fixing their specific problems? Any advice on just how far to go with one company?

Jen AbelThat is the founder's job. The founder's job is to have a clear vision and do not let anything delineate from that. It's important to take feedback in terms of what is the market's reality, but it is the founder, and this is why being a founder is so hard. It is the founder's job to interpret that because a lot of feedback you get is this is the old way, they're responding this way because it's the old way of working.

They want you to build this because that's how they're traditionally expecting to do that. It is not, "Here's where we're going, this is why we're not doing that. I hear you, but here's why we're not going to do that because we're going to completely change the way you do this." That is the founder's job.
And I think we did a bunch of design partnerships late last year and there was a lot of feedback given, a lot of feedback given, but the founder had such clarity with where he wanted to go that he was like 80% noise, 20% had I not asked this question, I wouldn't have gotten that gold in terms of where they are today. And it's that 80/20 rule where 80% of what they're going to tell you is probably going to be not related to where you want to go or based off of the old way, but that 20% of, "Oh, I did not think about it that way." That drives everything.

Lenny RachitskyHave you seen a design partner pull a company in the wrong direction? Just screw their path? Have you seen that or is that pretty rare?

Jen AbelNo, I don't think it's that rare. We hear people complain about it all the time, but I think it's more of an excuse.

Lenny RachitskyComing back to this question of going after the enterprise versus SMBs. And again, early advice you gave is there's no, don't go in between. Either pick SMB small company, which I know you said there's a million ways to differentiate what this means, but I guess I think of employee numbers under some number over a thousand is maybe enterprise. Is that a good way to think about it just like-

Jen AbelYeah, it depends. Are you selling per seats or are you selling based off of usage or are you selling off of, I think it also depends on the pricing model a little bit. I look at headcount too because it's just such an easy way to think about it because you can also gauge usage off that and a bunch of other things, but sometimes the small companies, I think we're going to see a lot more larger companies become smaller because of AI, not significantly smaller, but also high margins allow them to experiment more too.

Lenny RachitskyThat's such an interesting point you're making there that the way we designate enterprise versus SMB like may shift because number of employees may go down with AI.

Jen AbelYeah. Oh yeah.

Lenny RachitskySo interesting. So where I was going to go with this question is when people are deciding, I'm going to go enterprise versus I'm going to sell to startups, like YC companies are the typical example they sell to their own YC batches and you just broad advice of picking, "Okay, we go enterprise versus no, let's actually go startup."

Jen AbelI think it's about, and I read this somewhere and I wholeheartedly agree with it because I've seen it live. I think it's about what game does the founder best understand? Are they an incredible marketer and have some competitive edge for how they can win a massive audience?

I would say go SMB and marketing led or are they a bit more really understand how large corporations work and really excited to deliver on $100,000 plus type of opportunities or the value that they are building for is way more relatable to an enterprise versus a small business.

Lenny RachitskyThat is really interesting. I've never heard of it described that way. I think about linear, which started very startup-ey and my take is they did that because changing the way you work is really hard and their bet was like, "Let's start with companies and grow with them and over time that becomes the default." Any reaction to that?

Jen AbelI think that it sounds like that that's a great way to work because that's a technical tool, so that you need the right, also need to have the right infrastructure to sell. I think Slack, look, Slack and Microsoft Teams are still battling it out at the enterprise. I think it's also how you plug in and how you integrate and do they even have the right systems to support you? The thing with open AI is they didn't have to connect to anything.

Lenny RachitskySay more about that.

Jen AbelSo the value, people were bringing their own use cases to it and it's not like they, well they can ingest and they built that, it's a brand new thing and they started I think, this is someone told me this, so this could be hearsay, but I believe that they were already speaking to CTOs even well before they released to help them explain where this is all going and get their buy-in.

And it's much easier to get into the enterprise when you're like, "We won't even touch your data, won't even touch your data. Just use it to solve problems and then we can build trust and then start to integrate and connect the pipes." But part of the challenges with selling in the enterprise, they're like, "All right, well let's connect all your data in the ..." "Whoa, that's extremely risky."
So you have to start small and low risk, which is like, "Hey, what is the subset of consumers that churned? Let's figure out how we could have made them happier, whatever it be." So that data is lower risk. So again, it's also understanding your market and understanding what their ability to experiment is.

Lenny RachitskyIt's interesting this distinction between OpenAI right now, and Anthropic, I don't know if you've been seeing their growth, it feels like OpenAI is very consumer first and Anthropic is more and more winning on B2B. I saw this chart recently where they're overtaking OpenAI now on B2B. I don't know, any reaction there of just these two different approaches?

Jen AbelI don't because most enterprises I'm talking to mentioned Gemini.

Lenny RachitskyOh, interesting.

Jen AbelOr Microsoft Copilot. So I don't hear much about Anthropic to be honest. So that might be more of a small business startup-ey, I don't know or it's a different part of the organization that's using it.

Lenny RachitskyYeah, that's a whole discussion or bundling right there of Slack and teams and then just Gemini just kind of coming in automatically. People don't have to adopt anything new.

Jen AbelYeah, totally.

Lenny RachitskyThere's something else that you talk about that I love that I don't think people talk much about, which is that enterprise sales is very creative.

Jen AbelOh yes.

Lenny RachitskyTalk about that.

Jen AbelSo I personally believe that small business sales is really a, I used to think it was more science than art. It was more figuring out what didn't work, running experiments, testing and validating, which I do believe, that's to get to foundations, where do we play? What do we want to do? Like that early, early, early zero to one.

From one to 10, I think it's more of an art, which is how do I take my learning and how do I package it up where I own the framing, I can speak to very specific alpha, I can vision cast and where I better understand the problem over time better than the market does. And it's all about deal crafting.
They just need to feel like the value they're getting out of it is way more than the cost. And it's sometimes about giving away things that don't really cost much to you, but are super expensive for them. For example, "Hey, we're selling X tool. We can build out Y specifically for you over the next year and integrate it because I know that you would've spent X number of dollars on engineering resources or you wouldn't have gotten in engineering head internally to do this, but we're just leave it to you. You got to give us a year to build it out."
Again, you're not letting them sidetrack you too much, you're kind of containing it. "We'll do that for you at no additional cost." That's huge value. Right? Or, "Hey, we're going to run an event and we want you at the forefront of it. We want you to be a speaker." Huge value. So it's like all of these additional things that add value beyond just the product but are all part of the product and the vision. Everyone keeps thinking the product is just what goes into their hand.
The product is pricing. The product is the opportunity, the framing and not letting them compare you to something else. And I know we talked that on our first call, which is as soon as you become a comparison, as soon as you become one of three that they're testing out, you've already sort of lost. It's all about differentiation and it's all about here's what you will be able to do tomorrow because of how we're going to serve you today.

Lenny RachitskySo along those lines, it reminds me in our first chat you actually made this point that I've never heard anyone else make, which is that services are a really good way to start getting into the companies that were most founders here. Like, "No, don't do manual stuff for the company. Build a product that you can scale." Your advice is the opposite. Actually start with self-services. Talk about that.

Jen AbelEnterprise is the number one thing they buy services, they know how to do it's super easy, they do it all of the time. It's like the most consistent thing they do. It's their largest budget item, external resources, consultants, whatever.

If they have a very immature way of understanding the problem or they've never purchased technology to solve it to some extent, either one, you are doing something that's never been done before, which is rare in today's day and age, or they might just be laggards on the journey. So you have to decide is this someone you really want to be working with? And if so, selling them as service, even though the technology is powering it on the backend is the fastest way to get your foot in the door.
It's what they know how to buy. Now, the idea is to once you sell that surface, once you get that foot in the door, then it's to guide them towards the product. "Hey, you're spending so much here, why don't we get you to come in and leverage the tool that's been powering this the whole time and move this more into technology serving you versus the human."

Lenny RachitskyWow. I think this will blow a lot of people's minds.

Jen AbelPalantir, this Forward Deployed Engineer, that's exactly what they're doing. There's a lot of companies out, I'm sure OpenAI, and this is what someone told me they were in and talking to CTOs and helping them better understand how AI and their organization can better work together. And it was them coaching them, educating them, whether they did it for free or not, I don't know, but they got their foot in the door, they started to build trust and then it gets adopted.

Lenny RachitskyThis is the epitome of doing things that don't scale that advice we always hear this is like, "Okay, this is what that looks like. We will solve this problem for you. We are using software to do it." And then over time, "Oh, you could just do this yourself. It'll cost you less. You can scale this."

Jen AbelYep, that's right. And they don't even need to know at first that software's doing it. That could be the magic part, which is like, "Guys, we literally, we are literally doing this with our technology."

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There's a lot of talk these days about this idea forward deployed something volunteer was really famous for, just essentially an engineer sitting in your office solving problems with you basically as an employee. And then through that, they learn what software to build. Is that something you're seeing too?

Jen AbelOh yeah, I think that a lot of companies, sorry, a lot of folks that serve the enterprise, they have a butt in a seat in their office. You look at these large consultancies like McKinsey, they're not in their headquarters, they're in their client's office all the time. And the other interesting thing and proof of this is how many people go to a Deloitte or Accenture and expect them to be a channel partner?

This is exactly what this is all about, which is they sell this service, they come in and then they introduce, "Hey, look at what this startup is doing over here. You might want to give them a shot. The problem with channel partnerships and why I don't believe in them is there are a hundred of you on this list and you're expecting them to sell it on your behalf."
Biggest no-no, they're not vision casters, they're not visionaries, they're consultants, but it goes all towards go. I remember startups saying, "Oh, I'm going to go win over Accenture and then have them disseminate me into their clients." And I'm like, as if that's a workable strategy.

Lenny RachitskyOkay. You know what might be helpful is, let me try to summarize some of the best pieces of advice you've shared so far. And this is specifically for folks trying to go from about a million ARR to about 10 million ARR. And then I want to ask you just what's most different about these two stages, but let me share this first. So advice one is go for tier one logos earlier than you think you should because they're early adopters, they can move fast, they can pull you in the right direction.

Jen AbelAnd they excite investors too.

Lenny RachitskyYeah, for sure. And other leads are.

Jen AbelYeah, and other talent, future employees. Yeah, exactly.

Lenny RachitskySo the counterintuitive insight here is you think they will move slow and be too busy, but they are actually the early adopters.

Jen AbelThat's right. They have to maintain that number one spot. And also, all of the people that are in the number two, number three, number four spot, all want to do what number one is doing. So it's also pure referenceability too.

Lenny RachitskyAnd the point about them being the early adopters, the people that join the Stripes in OpenAIs and Anthropics are like they individually love technology and love the latest stuff. So as a human they're like, "Oh, this is cool."

Jen AbelThat's exactly right. I'm just agreeing with myself, that's kind of funny. But yeah,

Lenny RachitskyThat's a good sign. So two is ideally try to price closer to about a 100K, like 75 to 150-ishK is what you said. Most enterprises are used to buying. So instead of starting or even sticking with 10K, 20K for too long, you need to make yourself go towards 75 to 150K.

Jen AbelThat's right, yep. And if you were to sell a service, I know we're talking about selling services first, throw weight that over time, so maybe it's 10K a month. So they start to get used to what that pricing looks like.

Lenny RachitskySo this is a way to make it feel, this is like how you get to 75 to 150K is there's a service attached to it. It's not just, here's my SaaS product, we will solve this problem for you, or a person will be sitting there doing this for you.

Jen AbelOr no, it's the technology too. You can add the services. I always, well let me take that back. Whether the services is bundled into it or not, some people will unbundle it, other people will say the services is a part of it. But yeah, it nets out to 75 to 150K. That's right.

Lenny RachitskyOkay. And you said that it's okay to start lower on ACVs and deals, but you need to push fast towards a 100K over a few months.

Jen AbelYep, that's right. If you can get into an enterprise for 10K in a month, which is not doable, but if you could, and you could go from 10 K to 50 K in four months through an expansion strategy all game, that makes sense, but it's really rare and very hard to do.

Lenny RachitskyAnd so there's two different paths there. One is land cheap and grow quickly. The other is move your ACV average up quickly. Seems like both, the latter is probably the more common strategy is just keep increasing prices.

Jen AbelYeah, because the former you can get tripped up because they could say, "Okay, now give me an economical price for doing this for a hundred people." And then it all kind of evens out because now you're at the 100K deal anyway, but it's much, there's more room for error, which is why I say go in and try to land 100K.

Lenny RachitskyBy the way, in our first chat, we talked a lot about the procurement process, which is what trips a lot of people up and is really painful. And I vividly remember that conversation still. So if people are having issues getting through the sales process and procurement, a lot of good advice there.

Jen AbelAnd getting stuck in procurement is usually because you're not speaking to a senior enough person and they don't know how to navigate it, which is why I'm like that executive needs to be involved because as soon as the executive picks up a phone and tries to get a hold of their buying group, things move.

When people say, "Oh, I'm stuck in procurement." I'm like, "Oh, that could just be a qualification error and you never get out of it because you sold to someone too junior." So that's why the 100K is such a safe zone because even for 10K, you might have to go through procurement. So this is the surest way to make sure that you don't ... Listen, I've seen 10K take nine months to close.

Lenny RachitskyNo bueno.

Jen AbelYeah, so.

Lenny RachitskyOkay. Next piece of advice is this idea of vision casting instead of problem solving. So the advice here is instead of here's your problem, here's how our product solves it is here's how you will achieve alpha in the market by adopting the software. We talked about the example of cursor where if you adopt cursor, you're going to draw the 10X engineers that are joining other companies right now. This will give you a big advantage.

Jen AbelThat's right. And yeah, it's pain versus opportunity, especially in the age of AI, and I know that we're moving into the next dimension. It's all about solving for a gap. It's seldom about solving for a very, very specific problem because people are trying to figure out what's our AI strategy? Where are we going to go with this? What is the world going to look like? I want to be a part of that new world. So it's a great time to be doing that.

Lenny RachitskyAnd then there's a bunch of advice you shared about design partners, of just how to select them. Your advice is definitely have design partners because they will help you build the right thing. But as a founder, you need to have a clear vision and sense of where you want to go and not just build everything they're asking you to build.

Jen AbelThat's right, because important to say no. And that's all part of the framing, which is like here's, we want a little skin in the game. You set the price, but here's what we're marching towards in the next six to 12 months. Are we aligned there? If we deliver on what we say we're going to deliver, are we aligned there and do that kind of handshake?

Lenny RachitskyIs there anything else that I missed that you think is really important for this stage?

Jen AbelSo one to 10 is no longer the founder. Maybe the founder comes in very strategic points, but you need a really good enterprise salespeople. Taking someone from small business and expecting them to do enterprise sales, big no-no, it's a different game, right? Vibe like a different game.

You need to understand how corporations buy. You need to understand how executives think. You need to better understand simply just what the enterprise business model is all about and their ability to take on risk. People will bring in super junior enterprise sales reps and I'm like, "You're looking to sell to an executive and you have this person that's five years out of school with no corporate experience doing it, again, unless they have some extremely deep experience in the industry or are just a unicorn in terms of, wow, this person can sell ice to an Eskimo kind of thing."
A junior person converting an executive, again, if the founder is involved, maybe that's doable, but usually the founder can't be involved in every deal and you need people that can, I always say you need people that can cosplay a founder, which is selling the vision, getting them excited, running through a wall to get the deal done and getting creative on ... None of my deals look exactly the same, every deal looks different and that's okay because every organization has slightly different opportunities of where they want to go, and you have to kind of build towards that and the framing may change.
So it's this ability to adapt from what you're hearing and let that compound over time, but I always say, can this person cosplay the founder? I think that that's the best type of salesperson because it doesn't feel like sales. It's more of the art.

Lenny RachitskyThis is amazing advice. What is a common profile that you've seen be successful? What level of seniority? What kind of personality and any traits to look for?

Jen AbelMaybe a former founder if you can get that, because they're used to selling, they sold investors and they've sold employees. Two is someone with no sales experience, but has deep product experience or an engineer and can think about things in a unique way where the market is like, "Oh, this is so interesting."

Taking a typical salesperson then and putting them into a sales role almost always is where people get frustrated. The market, it feels salesy. The market doesn't want to be sold to, they want to buy. And I know that it's very hard to hire a really good enterprise salesperson. The number of people that I've interviewed, I can count on my hand the ones that I get really, really excited by.
It's almost like coming across a great founder. It's not as common as everyone expects, and I think that that's true for engineering. I think that that's true for sales and I think a lot of people, sales is like, "Oh, just throw a body into it. The product will do the work."

Lenny RachitskyAdvice I often hear is don't hire a senior VP of salesperson from a bigger company. Do you agree with that? What's like to senior?

Jen AbelYeah, so the bigger company thing, the brand was doing all of the work. The brand built the trust. You need this person to be able to build the trust and they're usually, the product is still so new. The product is the founder in the zero to one stage. The product is just starting to get a case study.

You probably have maybe a few references, but it's still very, very early days. You need the market to believe the salesperson and you need that market to know that they're trustworthy. A VP of sales at a large company, I would say, they're best suited for a large company because one to 10, you're running through walls.
You have to figure out, you're doing a lot of convincing, you're doing a lot of educating, you're doing a lot of creative deal crafting. A lot of owning the frame. It's not necessarily selling a product, it's selling that future value, which a VP of sales at a large companies, it's very different. It's a different game. It's kind of like the SMB and enterprise.

Lenny RachitskyIt's interesting you said when you described the profile of a great hire here is you said they don't need to have done sales. If they have done sales, what's a number years or kind of what do you look for that tells you, "Okay, this is a good fit for the first hire."

Jen AbelI actually think it's less about experience and more about the person. Does this person make you feel good? Do you want to buy from this person? I think Jason, Jason Lemkin said that best. Would you want to buy from this person?

Lenny RachitskyCan they sell you a pen?

Jen AbelThe classic. Yeah, exactly. Do they mimic or mirror the market they're selling to? It's much easier to buy from someone that looks and feels like you than it does from somebody that's in a totally different realm. And also, an executive wants to talk to another senior person.

They don't want to talk to someone that just graduated from college and is selling them the new way of working. What do they know? So I think it's tricky. I would say someone with no sales experience makes it feel different and special, that's what I like about it. Someone with sales experience knows how to navigate and probably be qualified better, but it's almost like the blend of those two things.
And that's why I go back to cosplaying the founder, which is like, could this person close a future employee? Do they get excited about the problems they're solving internally and the vision that they get to sell to?

Lenny RachitskyThis actually was a reader question, listener question from Twitter. So Peter Dedenne asked, "How do you make this first salesperson as enthusiastic about the product as you? Is there something you could do? Is it more just they already are and you just leverage that?"

Jen AbelIncentives. Salespeople love to make money.

Lenny RachitskyEasy.

Jen AbelSo if they know it's possible, if they know it's possible, you'll be shocked what people can get done.

Lenny RachitskyIf they see how much they could make. Amazing. I imagine there still also has to be an innate excitement about the product and the opportunity.

Jen AbelThey have to believe in it. They have to believe in the founder, but incentives usually make the world go round, but yeah, is this person, are they asking the right questions to the founder? The best thing to do is have the founder join the first five calls. You know after five calls if this person has what it takes, and don't be afraid to fire. One in every two salespeople usually are fired. Yeah, it's a very high failure rate.

Lenny RachitskyBecause you can tell pretty quickly how it's going.

Jen AbelYou can tell, or the vision of the founders is just very wrong.

Lenny RachitskySpeaking of incentives, do you have any quick advice on how to structure their comp? Just like how much they earn?

Jen AbelIt's usually 50/50. So it's 50% OTE. So it's 50% base salary, 50% OTE.

Lenny RachitskyAnd then how much of the sale do they typically get? Say the first sales hire.

Jen AbelIt depends on the size of the deal, but in technology, it could be anywhere between eight and 12%. So rounds out around 10%.

Lenny RachitskyOkay. Awesome. When do you hire the first salesperson? Is it around the 1 million ARR mark usually?

Jen AbelYeah, it's around that 1 million ARR, mark and I, and it's usually when you have your first seven to 10 customers and there's some pattern recognition around it that you can share with somebody else, there's some consistencies. Otherwise, it's just like that would be very hard.

Lenny RachitskyBasically as a founder, you have to figure out how to sell enough times so that you can show someone, "Here's what's working."

Jen AbelAnd this is the common thing I hear, "Well, I'm a $10 million business. I'm in this small business space. You're $0 in enterprise." It's a zero to one right now in enterprise. It's a totally different game. It's a different value proposition, it's a different deal structuring, it's a different target market. It's a different risk tolerance. It's totally different. So don't be blindsided when-

Lenny RachitskyIt doesn't work.

Jen Abel... There's a lot of unlearning that needs to happen when you move into a new market.

Lenny RachitskySo the advice here is make yourself sell up until around a million ARR, especially if you're trying to go enterprise selling to enterprises yourself as a founder, which is really hard. You have so much to do and you have to be selling this thing for a long time time.

Jen AbelYep. And then try and find someone that you get excited by. It's funny, if you ask the founder, are you excited by your salesperson? I'm curious what the real answer is. It's like, "Well, it's a button to see it in. It was hard to hire, so."

Lenny RachitskyInteresting. I remember, I think it was Jason's advice was to hire two people immediately.

Jen AbelThat's right.

Lenny RachitskySo you can compare them. Do you agree with that?

Jen Abel100%. Yeah, because of the 50% failure rate. I think that's exactly right. So yeah, even a tall order, go find two people that are good. But yeah, I think that that's right because one in two will fail.

Lenny RachitskyOkay, let me ask you another reader question from Hang Huang. This is kind of in a different direction. So he says, "The biggest challenge is always cutting through the noise to get that initial meeting with the right decision maker. How do you even get their attention?"

Jen AbelIt's the vision. What is the opportunity that you're selling? That if they are excited by that, they will take a call. I see it all the time, and don't give away the farm. Keep it to three sentences. And I know I said this on our first call, but say something counterintuitive, they could feel different. Make it feel like they can learn from you by taking a 15-minute call. You see the standards of like, "Oh, I came across your LinkedIn." And, "Are you looking to grow your business by 15%?" It's like, "What kind of statement is that?"

Lenny RachitskyAnd this is in the cold email they get about this pitch.

Jen AbelYeah.

Lenny RachitskyAwesome. So this is a good segue to another reader question from Hugo Alves, Co-Founder of Synthetic users. He asked, "What's the best advice for going from healthy inbound to targeted outbound?"

Jen AbelHealthy inbound usually is a marketing-led initiative. So that's a marketing game. It depends what deal value you're selling. Are you selling a $5,000 deal? It's got to be marketing-led to make the engine work. If you're selling $100,000 deal, you're doing outbound day one. So again, it breaks it into those. This is like that blending of the, I see a blending of that question. This is where you're doing small business marketing-led activities or are you a sales-led organization selling a $100,000 deal?

Lenny RachitskyAnd the reason that's important, just in case it's not obvious, is you're not going to make money if you're selling. People are spending time closing deals that are making 10, 20K. Just the ROI on that won't work for your business model.

Jen AbelThat's right. Yep.

Lenny RachitskyAwesome. By the way, let me just say, Jen, this is an incredible conversation already. We've gone-

Jen AbelOh this awesome.

Lenny Rachitsky... Through so much. This is exactly what I was hoping to get through and we've gone through so much advice that I think is going to be so helpful to so many people. There's a few things that your partner, Justin also suggested I ask you about that I want to touch on. One is you have this question you ask founders a lot that opens up their mind. You ask them, "If you give your product away for free, would people even use this?" And every founder is like, "Of course." And then you ask, "A customer this?" And they're like, "Nah, we wouldn't use this." And that just blows their mind. Talk about just the power of that and how you recommend people approach this.

Jen AbelI always say ask the questions you're afraid to because that truth is going to get you closer and closer to the answer. So I'll ask a client straight up on a call, I'll say, "Honestly, do we think we're going to get the deal done this year? Is it possible?" They'll give you the real answer and people are afraid to ask. But the other side is sort of if they're in it with you, they don't care about that question, right?

Can't ask that question on day one, but if you are, and we didn't talk about this, but maybe this is important. Every single enterprise deal I have done, the deal is done, the deal is closed and pretty much done through text. It's not on email anymore. It is a relationship you're building with someone where if my enterprise client called me, I'm picking up that phone immediately or I'm responding them to immediately because that builds so much trust.
If they know they can call on you, they're going to get you to pick up and they know that you're going to do everything humanly possible to make sure that this is successful. People will turn over rocks for you. I have a client at a Fortune 10 company where I was like, it's so important we get the deal done this year. Is that possible? And she's like, it's a tall order, but if it's going to help you, let's do it.
These are how enterprise deals gets done, it's relationships and it's this, and this is why I'm saying structuring the deal, make it feel like you went to bat for them and in often cases, you are going to bat for them and structure it in a way that makes sense for them. Everyone kind of just tries and pigeonhole. Pigeonholing and deal structuring consistency is important for a $10,000, sub-$10,000 deal. A $100,000 deal, it very commonly will look different every time.

Lenny RachitskyApril Dunford was on the podcast and she shared this really interesting insight that the reason people behave this way is the person at the company buying this thing, their ass is on the line Also, their reputation is on the line for this thing to work out. So they want it to go really well.

Jen AbelThat's right. Again, they do this one in every three years, one in every two years, maybe one in every five years. Hell, I don't know. They don't do this every year. It's very rare. It's no one likes a new tool. No one. Not you, not me, unless it changes everything.

Lenny RachitskyYeah. Figma was a great example, that's Slack.

Jen AbelEverything you've touched

Lenny RachitskyEverything that worked out. You said that you asked these questions that people are afraid to ask. What are some other examples of questions you often ask that people are afraid to ask?

Jen AbelI will say, "Listen, this is $150,000 engagement. I will co-author it with you where we can make this a little bit bigger if you need something else. We can make it a little bit smaller in year one, but in year two it steps up. How do we get this done so when you go to bat, it's a win?" Sell them, do they take it to the wrong side and try and discount you? I've actually never seen that because at that point you have a relationship.

So co-authoring the pricing is so important because they need to know that they go to bat, they can say, "I got this out of them. If we get this deal done." So this is why when I say every deal looks the same, you're asking great questions because it's explaining why I meant by that, but this is another example of why every deal in the enterprise sort of looks somewhat different because a lot of it is co-authored. So again, if someone wants a slightly lower price, give it to them, but maybe them lock them in a little bit longer.

Lenny RachitskyThere's another point that Justin makes that you've touched on a bit, but it's when your no, the way he phrased it is, Jen always talks about how no is the best answer to yes because no is data that you can use. Talk about that.

Jen AbelI am a qualification crazy person. I will not get in on another call with someone because on the first call it's either a yes or a no, there's no in between. Humans are, we're so different and we're so unpredictable, but we're also so predictable at the same time, right? It's very obvious if someone is excited and wants to do something, it is so obvious when someone is just trying to be nice.

So I will say to them on that call, "I'm sort of getting the vibe that this might not be a good fit or might not be good timing. Did I misinterpret that?" And they will usually say, "Yeah, you're right, it's probably not a good fit." And then immediately, "Great, I would love to stay in touch. You've just saved a relationship and you've just saved yourself a ton of time."

Lenny RachitskyAnd the implication here is just to your point, you're limited on time. You don't want to be spending time going down or rival that won't you anywhere.

Jen AbelYeah, exactly.

Lenny RachitskyI'm going to take a quick tangent on tools. What's the state of the art on go-to-market outbound tooling?

Jen AbelI don't use a tool because I believe in the manual and I'll explain why. Every single note I send is slightly different because I see a picture of them and I'm like, "Oh, I don't know if that's going to land." Or I'm like, "Oh, they actually might appreciate this. It's weird." Visual cues are so helpful. A picture is a visual cue, looking at how long they've been in the role, looking how long they've been at the company.

I use all of these little things and I seldom customize a note in a way that people expect which is that first customized sentence because AI does that, and everyone's doing that. So I go the opposite extreme, which is like remove it and I customize it with how I frame it or the subject line. So it's like if I'm talking to someone like a peer, I might say quick question like QQ.
If I'm talking to someone that has a bit more experience, I might write a little bit of a tighter note, not all lowercase. So it just depends on who you're speaking to. And again, this is why it's okay to spend a little bit of time on this because it's a hundred thousand dollars. It's actually a million dollars at the end of the day because a $100,000 deal if you play your cards right turns into a million dollar deal over three to five years.

Lenny RachitskyI love how much you enjoy this. It's so fun to, so essentially what are you doing? You're sitting on LinkedIn finding folks to ping and then you cold email them one individually, manually.

Jen AbelIt's so weird, Lenny, I have no process. I kind of just go with the vibe. I'll read an article about Tesla and I'm like, "Huh, they could be interested in this." Not because that article had anything to do with the problem I'm solving, but because I'm like, "This feels like a good Tesla day." It's hard to describe. It's a very emotional thing for me, and not to toot my own horn, obviously, but I've been successful in sales and the most successful sales people can't explain why they're good at it.

It just comes to them naturally. It's just like an emotional thing. It's like the world's best founders. How do you be a good founder? It's very, very hard to define. How do you become a good engineer? Very, very hard to define. So I don't believe in playbooks. I believe that there's a feel to it. I emailed a chief legal officer at a hedge fund once and he responded to me because I wrote to him on Saturday. I knew it was going to be busy. I made it one sentence and it was tweaked for him.

Lenny RachitskyDo you feel like this is going to be the way as AI SDRs just kind of take over and everyone's getting billions of emails that feel AI-ish?

Jen AbelYes.

Lenny RachitskySo I guess maybe speak more there. Just like is the alpha essentially just become human? Don't automate? Should you think you should?

Jen AbelThe thing about AI tools is they're all pulling from the same databases. So I'm like, "I want to email someone not in the database that's getting hit by a million folks. I want to take a back door in, not the front door where everyone else is trick-or-treating."

Lenny RachitskyAnd this is effective for very large deal, which is what you need to be doing anyway because it takes a lot of time to do it this way.

Jen AbelYeah.

Lenny RachitskyInteresting. So you're not like sitting in Clay, you're not like Apollo, I don't have all those tools. You're just finding people yourself.

Jen AbelYep.

Lenny RachitskyDo you start with a target prospect list at least just like, "Here's the companies that are the perfect fit for this and let's work through them."

Jen AbelIt's all in my brain. I've been doing this for so long, I have in my brain, I'm like, these are my early adopters. These who I'm going to go to after I close those logos, they get excited by those logos. So it's just experience of you land a Walmart, you're going to go to the rest of the industry and say, "Hey, we're working with Walmart." Versus you go to some lower end enterprise company and they're like, "Wait, what do you do?" I can't even comprehend.

Also, the most strategic people, some of the most strategic executives are at these tier one logos. That's why they're tier one because they've got super smart, really capable folks. They also extract the best talent, the best talent likes to experiment and continue to improve. So it's like this compounding thing.

Lenny RachitskyFor someone that isn't Jen and has all this experience, say their founder, they're hit a million ARR. They're just like, "Okay, where do we find our customers?" Do you have any advice for just coming up with who we should go after? Should they be using these tools? Should they be hiring someone like a Jen? I know this is what you do for companies. So one crowd is go hire JJELLYFISH to help them through this.

Jen AbelFounder, the founder. I would say the founder, this is sort of in tune with them in a way. They just have to find it. It's so weird to say it's all, and I hate saying it because it's like a commonplace thing to say, but it's like there's this thing about flow and it's like some of these brands are in flow with you right now, right? You found this insight from somewhere. Who else? What's the next adjacent ring of people that would buy into that?

Lenny RachitskyAnd so what I'm hearing is just pay attention to what's happening, what companies are-

Jen AbelYeah.

Lenny RachitskyThe news, what companies are doing interesting things, who are the kind of early adopters in the market.

Jen AbelIf it was just a database list and it was just about figuring out the right messaging and then emailing folks, we would've known by that by now.

Lenny RachitskyThat's so interesting. Okay, maybe one more question. This again is from Justin. He shares that when you hit resistance, you never argue, you reframe. If someone says, "We already have X solution, you'll agree and pivot and totally X is great for this thing, but here's what we can do."

Jen AbelThis is why it's sell to the alpha. Hey, I know. Listen, that problem you just described, you're right. You have a tool for that. We're taking you much further upstream with value. This is the opportunity I want you guys to have access to.

Lenny RachitskyI love it, Jen. I've gone through everything I was hoping to get through. On the other hand, I feel like we could do another hour on all these things, I feel like we need to do.

Jen AbelWe have three.

Lenny RachitskyYeah, we need round three on the next phase and all the things that people want to dig further into. Before we get to our very exciting lightning round, is there anything else that you wanted to touch on or share?

Jen AbelThis stuff is really hard. It's very hard. Sales is also all about learning very, very quickly from the rejection. The rejection is good because it's a forced learning and you never want to go through that again, but you have to be, I don't like to use the word cringe. You can't be afraid to cringe is like bringing your AI recorder into a call, that's cringey, but sending 15 notes to people that you can deliver serious value to, don't be afraid, and don't be afraid to ask the hard questions. Be different.

The whole game is about, "Oh, this feels different. That's what people want access to." Yet everyone commoditizes themselves. They try and mimic what everyone, they try and mimic a forward deployed engineer. Just rename it. You don't have to use the same nomenclature. Everyone gets excited by the new because the new could be the next thing, the thing that changes it all. So that's why I'm always like, "Don't be better. Be different."

Lenny RachitskyAn amazing way to end it. With that, Jen, we've reached our very exciting lightning round. I've got five questions for you. Are you ready?

Jen AbelYeah.

Lenny RachitskyFirst question, what are two or three books that you find yourself recommending most to other people?

Jen AbelI do Twitter accounts.

Lenny RachitskyOh, Twitter accounts to follow? Oh, amazing.

Jen AbelYeah.

Lenny RachitskyOkay.

Jen AbelLenny, the day I have time to read a book.

Lenny RachitskyPeriod.

Jen AbelPeriod. I would love to be reading books.

Lenny RachitskyCool. Twitter accounts to follow. Tell me.

Jen AbelYeah. Look, obviously you, you produce some of the best content, truthfully,

Lenny RachitskyAppreciate it.

Jen AbelYou get into the minds of people that they're not even giving this insight on Twitter. Who else do I absolutely love? Jason Lemkin. So for sales, Jason Lemkin is awesome, awesome follow for sales, and also he had a great, great recording with you. So link to that because that was a great piece. I actually learned a ton from Matt. I love Gavin Baker. Super nuanced takes. Takes a lot of obvious statements, but shares a lot of the non-obvious insight. He's great. Jason Cohen, have you ever had Jason Cohen on the cast?

Lenny RachitskyJason Cohen, a Smart Bear Jason Cohen?

Jen AbelYeah, yeah, yeah.

Lenny RachitskyHe's coming on the podcast at the end of the year or something.

Jen AbelOh, that's awesome. What a great plug for him right there.

Lenny RachitskyYes.

Jen AbelYeah, those three would be great. I know they're all men, but.

Lenny RachitskyGreat tips.

Jen AbelYeah.

Lenny RachitskyNext question, is there a favorite recent movie or TV show that you've really enjoyed? I know you said you have time to read.

Jen AbelThis is going to be embarrassing, Baywatch.

Lenny RachitskyBaywatch.

Jen AbelYeah. Baywatch channel. It's just so Numby, and it's like '90s classic. Baywatch.

Lenny RachitskyWow, I've never heard that one before. So this is original Baywatch with?

Jen AbelThis is original Hasselhoff. David Hasselhoff.

Lenny RachitskyYeah, Pamela Anderson.

Jen AbelYasmine Bleeth. Pamela Anderson, the original cast.

Lenny RachitskyAmazing.

Jen AbelYeah.

Lenny RachitskyOkay. Deep cut. Is there a product you recently discovered that you really love?

Jen AbelSo the number one thing for me right now is an app called Playground, which is the pictures of my toddler that they upload into the preschool so I can get the daily updates on what's going on in preschool when he's not home.

Lenny RachitskyAmazing. I need that. We get emails and Google Photos. I would really love that.

Jen AbelYeah, there was another one called ClassDojo. There's a few of them, but Playground is the one that this preschool's on.

Lenny RachitskyLove ClassDojo. I'm a small investor.

Jen AbelAre you really?

Lenny RachitskyI am.

Jen AbelOh, that's awesome.

Lenny RachitskyHow about that? Two more questions. Do you have a favorite life motto that you find yourself coming back to find useful in work or in life?

Jen AbelYeah, be direct. Cut the fluff. Give me the bullet, not the paragraph.

Lenny RachitskyFinal question. I was told that by Justin that you've never read a sales book. You've just learned to do this. If you were to read a sales book, if there was someone else out there that you look up to, learn from, is there anyone else out there in the world of sales that you most respect?

Jen AbelI think Jason Lemkin has the strongest understanding of sales. His content is unbelievable. He speaks about it clearly and cleanly, I would say. And as I mentioned, unbelievable Twitter follow. I'm a big fan of his.

Lenny RachitskyAwesome.

Jen AbelI've actually learned a lot from him too. The 50/50 thing or a higher two salespeople, he's spot on. Failure rate is actually probably higher than 50%.

Lenny RachitskyI love that guy. And he's so AI-forward these days. He's just building. He almost took down Replit with his complaints. It was a whole new cycle of how Replit-

Jen AbelHe should interact. Sometimes he says things that are harsh, but you're like, "He's not wrong."

Lenny RachitskyLove it. I got to get him back on the podcast.

Jen AbelYeah.

Lenny RachitskyJen, this was incredible. This was everything I wanted to be. I feel like we just leveled up all the founders that have listened to this in their ability to close. We're going to just create all the economic value and a lot of happy VCs from all the sales that will be closed as a result of the advice you shared. Two final questions. Where can folks find you if they want to either work with you or follow you online? And how can listeners be useful to you?

Jen AbelTwitter. Every new learning or mishap, I put red on Twitter, so it's like my personal diary and super responsive on Twitter DM.

Lenny RachitskyWhat's your Twitter handle? Twitter handle.

Jen AbelIt's double J, So J-J-E-N_A-B-E-L.

Lenny RachitskyYou did not make that easy for people to find you, but we-

Jen AbelYeah, I know, I know, I know I didn't.

Lenny RachitskyAnd the J is for JJELLYFISH, is that where the extra J is for?

Jen AbelYeah, the double Js. Then also, well, someone else had the handle, so I was like, "I need my name."

Lenny RachitskyGot it. By the way, just tell people what JJELLYFISH is in case that might be helpful to them.

Jen AbelYeah, so it's a consultancy that helps folks in the zero to one stage, and now I'm at general manager of enterprise at State Affairs, which is basically giving citizens and corporations an inside peek into what's actually going on inside the state capitol building. State policy is way more impact than on you, than federal policy. Federal policy is written more about.

Lenny RachitskyIncredible. I've only recently learned that that's what you're doing these days, and that is super impactful and important, so thank you for your work there.

Jen AbelEven democracy.

Lenny RachitskyNo big deal. Jen, thank you so much for being here.

Jen AbelThank you so much, Lenny. This was a blast.

Lenny RachitskyBye everyone. Thank you so much for listening. If you found this valuable, you can subscribe to the show on Apple Podcast, 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 lennyspodcast.com. See you in the next episode.

Jen AbelYou need to vision cast, you need to sell to a gap, don't sell to a problem. When you're selling to a leader, you need to be selling an opportunity. The market doesn't want to be sold to, they want to buy.

Lenny RachitskyMost founders would rather get 10, 10K deals than lose nine and get one 100K deal.

Jen AbelIn the very early days, people will discount till the cows come home because they think that's the way to get a deal done. The best clients are not going to do that to you. If they're sitting there nickel-and-diming you, they're not fully bought in on what you're selling them.

Lenny RachitskyIt might be giving you a false sense of success and product market fit.

Jen AbelAs soon as you become a comparison, as soon as you become one of three that they're testing out, you've already sort of lost. It's all about differentiation. Here's what you will be able to do tomorrow because of how we're going to serve you today.

Lenny RachitskySomething else that you talk about is that enterprise sales is very creative.

Jen AbelIt's more of an art. It's all about deal crafting. It is a relationship you're building with someone. If they know they can call on you, people will turn over rocks for you. I have a client at a Fortune 10 company where I was like, "It's so important we get the deal done this year. Is that possible?" And she's like, "It's a tall order, but if it's going to help you, let's do it." These are how enterprise deals gets done. It's relationships.

Lenny RachitskyWhat's kind of like the state of the art on go-to-market outbound tooling?

Jen AbelI don't use a tool. The thing about AI tools is they're all pulling from the same databases. I want to email someone not in the database that's getting hit by a million folks. I want to take a back door in, not the front door where everyone else is trick or treating.

Lenny RachitskyToday, my guest is Jen Abel, co-founder of JJELLYFISH where she and her team help early stage founders learn how to sell and now GM of Enterprise at State Affairs. If you want to become better at selling your product, this episode is going to blow your mind and make you so much better in every way. This is the second time Jen's been on the podcast. Our first conversation was focused around getting from zero to 1 million ARR, essentially founder led sales.

This conversation is part two going from around one million in ARR to around 10 million. This is the most tactical and in the weeds discussion you will find anywhere for free on how to actually become more effective at selling to enterprises. I'm so excited for you to listen to this conversation. If you enjoy this podcast, don't forget to subscribe and followed in your favorite podcasting app or YouTube, it helps tremendously.
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Jen AbelLenny, it's starting to feel familiar and I like it.

Lenny RachitskyI should have said welcome back to the podcast. So I actually shared on Twitter that you're coming back and I had so many people ask so many questions. Clearly, there is a lot of confusion and a lot of need for learning how to get better at the stuff, we're going to talk about sales, enterprise sales to frame the discussion, our first chat, which we're going to point people to if they want to start there, we focused on founder-led sales, which is essentially the beginning phases of a startup, kind of going from zero to about 100 million ARR.

This discussion is on the next phase, which is going from about a million ARR to about 10 million ARR in enterprise sales, not like PLG or anything like that. You have a bunch of really strong and counter intuitive opinions and piece of advice on how to be successful at this. So I'm just going to go through a bunch of these things. We'll see where it goes. Before we get into the first one, is there anything broadly, I don't know, is there anything broadly you want to share? Anything you want to say before we dive in?

Jen AbelNo, let's dive right in.

Lenny RachitskyOkay. Okay, so the first thing that I haven't heard anyone talk about before is this point that you often make that the mid-market does not exist. People often hear about enterprise companies. There's obviously SMBs and startups. There's also people just, "Oh, I'm going to go after the mid-market." Somewhere between. You don't think that's real? Talk about your experience there, what people should know.

Jen AbelIt's fascinating because if you ask someone to describe the mid-market, actually, if you ask someone to describe the enterprise, every single person has a different answer. It's either based off of revenue, it's either based off of market cap, it's based off of employee size, and I think a lot of people can get lost because selling to a hundred person organization is a radically different game than selling to a thousand person organization and there's no hybrid approach.

So the best way to think about it is you have small business which typically can be really powered by marketing, and then you have enterprise, which is typically going to be sales led. If you bucket them into these two very specific silos, it makes it much, much easier to understand what game you're playing. Now, when we talk about mid-market, I usually will say, "Are we talking about the upper end of small business or are we talking about the lower end of enterprise?"
And most people are usually saying the lower end of enterprise. And I say, "Great, know you're playing the enterprise game. Know the type of people you need to hire, the type of ACV they need because it makes it a lot easier than trying to have this middle ground that catches everything that doesn't distinctly define SMB and enterprise." So I say the mid-market doesn't exist because what is a mid-market hire? It's either low end enterprise or upper end SMB, and if you bleed those two games you're going to lose. They're so distinctly different. So that's kind of my theory on it.

Lenny RachitskyYou have this chart that you shared with me that will link people to where you kind of show the number of companies within each of these segments and there's basically nobody in this kind of middle segment, talk about that a bit.

Jen AbelThat's right, and just like the power laws, if you look at the Fortune 1,000 and then the lower end enterprise from there, it trails off so fast. Power laws totally exist in these large corporations and we can't be treating everyone the same.

Lenny RachitskyThis begs the question, where do you suggest companies start? There's obviously startups classically are just like innovators, move fast, can make quick decisions, enterprises have all the money. Usually the advice I hear is just don't go after the fancy companies to start because they take a long time. You don't want to screw it up. What's your advice on where to start for most companies?

Jen AbelThe exact opposite. Early adopters are those logos because they have to continue to stay at the number one spot. So they'll take tons of swings to continue to stay in the ... Staying in the number one spot is the hardest part. So those number one logos are like if you can give me just a slight bit of alpha, just a tiny bit, that's where I get promoted, that's where I get the pat on the back because we are the world's leader in our industry and we cannot be disrupted there.

So there's this running joke where not a running joke, there's this running statement where a lot of VCs will say, "Don't go after tier one logos, go learn down market." Or, "o learn from logos that don't necessarily carry a lot of weight." The ones that carry all the weight are the ones that are willing to take a shot and want to help, right? Because they also want to be, they also want to be able to dictate the roadmap.
Now it's the founder's job to decide what can be done and what shouldn't be done, but their voice takes you a $100,000 deal into a million dollar deal in a very short period of time. It will literally guide you there. So when someone says, "Hey, go after startups, such as short sales cycle." Yeah, that makes sense. I totally get that. It's very easy to define the decision maker.
It's very easy, you don't have to go through procurement, but in the age of AI where it's all about sucking the oxygen out of the room and winning the deal and getting your foot in the door as quickly as humanly possible before someone else tries to take that, you want to get to the enterprise as fast as humanly possible.

Lenny RachitskyJust so folks understand what we're talking about here, when you say tier one, what's a good way to think about what tier one is?

Jen AbelTier one is like your Walmarts, your McDonald's, your NVIDIAs, your Tesla, your ExxonMobil, your UnitedHealthcare, the logos that are the leader in their space, their job is to stay in the number one spot.

Lenny RachitskyWow. Your advice is because this is very counterintuitive. This is exactly what you're here not to do. Your advice is go after the Chevrons and the Mobils and the Walmarts as a startup.

Jen AbelBecause if you can get them, that's all the proof you need.

Lenny RachitskyHow do you approach finding someone? Let's just get tactical there. Just like say you're going after Walmart. I know this is not a five-second answer, but just how would someone approach finding someone at Walmart to sell to?

Jen AbelFirst of all, make sure the founder is involved, right? Everyone loves talking to a founder, so we'll start with let's get the founder involved as fast as human possible. The second is you need to vision cast, you need to sell to a gap, don't sell to a problem. There's a very big difference between problem selling and gap selling. Problem selling is highly specific, more technical than not, and it's the way that every salesperson is going to go about it, find the problem and anchor to it.

When you're selling to a leader, you need to be vision casting and you need to be selling an opportunity which is they are here, here's where we can take you. You know that image where it's like Mario or Mario, and then there's the mushroom and then there's Mario on blast, and everyone is like, "Don't sell the mushroom, sell Mario on blast." Well, that's exactly what it's saying.
It's about selling the opportunity. That's what gets the tier one logos excited and that is the best thing for a founder to sell, selling the vision versus the problem, and also it's what gets them to want to take a swing. Who wants to take a swing because you can do some small problem? They're not going to go to bath for that.

Lenny RachitskyWhat's an example of a vision cast in a company you've worked with just to make this real? What does it look like when you've done a great job?

Jen AbelWe have an ability to deliver alpha, meaning, we have information, we have data, we have a way of working that no one else can do or is going to unlock a new way of thinking for you or an ability to deliver to a customer or an ability to solve a problem. Right now, you have an ability to access this level of information. I have an opportunity through our resources or through this gated data, we have access to get you much further upstream so that you can get information faster sooner. It's kind of like the high-frequency trading that one second, that one second. They didn't do much. They didn't sell, "Oh, we're doing fiber cable connectivity. We're giving you one second of alpha before everyone else." It's more of that ability and that's not problem-selling, that's opportunity selling.

Lenny RachitskyI like this phrasing of just giving them alpha, that's such a simple way to imagine what this should feel like. We'll link to that image you're talking about with the Mario and-

Jen AbelYou know that image?

Lenny RachitskyYeah, the person that made that image originally is Kathy Sierra, if you remember her, do you remember? So there's this person, Kathy Sierra, she's from back in the day. This was a big, I don't know, lesson she taught is you want to not sell your people on a feature or a product. You want to sell them on them becoming a superhero.

Jen AbelYeah, that's right.

Lenny RachitskyThey are now a superhero because of the thing you've built for them. And so the vision here is here's how you become a superhero. Here's how this alpha will help you become more successful.

Jen AbelAnd that's why founders are so good at selling because they naturally go to vision selling and vision casting versus a typical trained salesperson is find the problem, ask these questions and it just kills the vibe. It just feels like you're talking to a salesperson, right?

It's like, "What's your script? And it's like that's not vision selling, that's like playbook selling." And in the age of AI where a lot of it is Alpha, it's about speed, it's about getting access to information, it's about training data, and look at how the market is reacting to it. It's all opportunity and it's all about the alpha.

Lenny RachitskySo just to make this more concrete for people, Sam, like sales person at Cursor, what would be an example of vision casting? The obvious idea there is your team will be more productive, you'll get more done faster than everybody else. Is that a big enough vision to cast?

Jen AbelI think it may be more of you'll be able to actually hire the 10X engineers that you don't necessarily have access to because they want to be able to use this type of tool. It's about letting them get differentiated talent or that's probably more of what I would anchor to of this is the 10X engineers use cursor. You don't, do you want access to 10X engineers?

Lenny RachitskyThey won't even join your company if you're not using Cursor.

Jen AbelYeah, yeah. Think about it. So many people are so specific about what they're able to, I think especially technical folks, I'm not a technical person, but I would imagine that they're not going to go to, they don't like to go to these corporations because they're forced to use some incumbent tools.

Lenny RachitskyGoing back to going after these larger companies, I asked your colleague, Justin, what he sees you do that most impacts the success that teams have with their sales process. And there's a bunch of I'm going to touch on, but one is most founders are insecure about asking for large ACVs for charging, or the way he put it is most founders would rather get 10 10K deals than lose nine and get one 100K deal. Talk about your advice there and what you see.

Jen AbelThere are in the very early days is people will discount till the cows come home because they think that's the way to get a deal done. The best clients are not going to do that to you because that's like a qualification criteria, which is like if they're sitting there nickel-and-diming you being like, "No, I don't believe it's worth this. I don't believe it's worth that." They're not fully bought in on what you're selling them.

So when I say I'd rather get $100,000 deal than $10,000 deals, I'd rather have one rock star client that's going to help me figure out the next stage of where this is going than 10 or maybe five that are a good fit, five that are not, and I still have to serve those five that are not a good fit, and that's going to distract me. So this is why I love enterprise sales is they're not going to do the hard work of bringing you in if it's not critical or if it's not, when I say critical, it's going to impact them in a way that they're going to make it successful, that's what I love about enterprise sales.
They have the resources to ensure that it gets implemented because most in today's day and age, if people are not using the tool, you just get rid of the tool. So they're going to want to make sure whatever they bring in, what they go to bat for, remember, they go to bat once every two years, maybe once every three years. You've got to make it feel incredible. You've got to make it feel like they're going to be a superhero going back to it.
Otherwise, what's the point? Because the way enterprises are structured is it is designed today to make it hard to buy because they want to make sure whatever you're bringing in, you really, really want it gets rid of the mediocre. I think this would be good and it gets to this is going to change the way we work. It's going to impact our ability to capture some form of alpha, however you want to define that for them and it's sticky because of that.

Lenny RachitskySo your advice here broadly is don't pay attention to the smaller 10K-ish kind of opportunities for a bunch of reasons. One is it might be giving you a false sense of success in product market fit. Two, those companies are maybe not as innovative and won't lead you in the right direction. Three are probably discounts just like your product than your pricing just gets thrown off.

Jen AbelYep, and also you don't really get taken seriously for 10K. You get way more taken seriously for a 100Ks, it's much harder to get a 100K deal done and an executive use needs to be involved. I'd much rather have an executive sign-off on something and spend two more months getting the deal done because you know that they are bought in, you can now ensure what kind of value do they want to unlock and maybe you have an opportunity to turn them into a user, which to me, in today's day and age, with our generation being the ones that are now the executives at these corporations, this is native to them.

Lenny RachitskyWho is this true for? Is the advice here basically, if you're trying to build a successful B2B company, everybody should be aiming towards these a 100K sort of deals? Is there a world where you can be successful with 10Ks for a long time?

Jen AbelIf you have a super high win rate in a massive market, because all you have to do is reverse engineer the math. If you need to generate a hundred million dollars in revenue, how many 10K deals do you need? And the expansion on a 10K deal is in parallel to that. Where can you go? 10 to 15? That's a 50% growth, much easier to go to a 100K to 500K because they want more bodies or they want more value out of you.

For an enterprise, they'd love to get more out of an existing customer. You're already trusted. So it's also about the type of company you are. If you're venture-backed, you can't be selling $10,000 deals to the enterprise, you'll get killed, or you've already lost the game because you're playing a small business game in the wrong sector.

Lenny RachitskyHave you seen startups you've worked with succeed in that 10K, 20K bucket or is it really, really rare?

Jen AbelIf they're going after the enterprise?

Lenny RachitskyYeah.

Jen AbelYes, if it's the first three months and then after three months, it turns into a 50K and then a 100K and it ramps up quickly. Sure, that makes sense. You got your foot in the door and you can expand it exponentially in a healthy manner. I think that that's fine. $10,000 a year, then going to 12, then going to 15, the math will break.

Lenny RachitskyThis is great. I feel like most founders to this are like, "No, no, we're kind of in that exception we'll be all right. 10K, we'll do 20K. That's crazy to consider 100K."

Jen AbelYeah, the math will break. And also, a really good salesperson, you're commissioned on a 10K deal, they're not going to get a great salesperson. They're going to want to be anchored to how can I sell a $250,000 deal? How can I sell a half a million dollar deal? That's the type of person you want.

Lenny RachitskyAnd a big part of this is this is a good lens to force you to build the product that you can sell for 100K, 500K.

Jen AbelYeah, absolutely. And again, this is about playing that enterprise game. If you're trying to sell, if you're a small business, if you're in the small business place and an enterprise company comes to you and is like, "I like this." Ensure that you structure it for an enterprise. Don't play the small business team with an enterprise company.

Lenny RachitskyTalk more about that. What does that mean?

Jen AbelLet's say you're PLG, and a big company like Walmart comes to and is like, "Hey, can we get access for three of our users?" And they're like, "This is so exciting." And then they sell them the small business pricing for three users to Walmart. Very, very hard now to go from those three users that you just priced them at in a small business way, turn that into 100K because now it's documented what they're actually paying for this.

So you're stuck. You've kind of anchored yourself to this price. Not to mention how are you going to unlock the executive high level value so that you can get that senior executive to buy in and stamp this as well. Otherwise, it's just going to be throwing it on the credit card. But again, you've just ruined your enterprise game because you're anchoring to a small business price.
So this is why when you bleed these two games, it's very, very, very dangerous because these are really smart companies. They're going to say, "Well, wait a second, I just paid $9,000 last year and now you want to charge me $90,000. Well, what's the step change in value? What's the 10X value I'm now getting?" That's super hard to prove.

Lenny RachitskySo the tip here is your initial price will really screw you if you get it wrong. And so obviously we're not going to give people the answer on their pricing strategy fully, but just is the advice just charged more or what would you recommend?

Jen AbelIt is enterprise companies are very used to a land, when I say the first initial contract, somewhat between 75K and 150K, very used to that. In fact, that's probably where you want to start because you also want to understand where can you grow from this. Start contained, don't say 150K and sell the farm. Say, "It's 150K, here's who gets access, here's the value we're going to deliver and here's where we're going over time." You also want them to know, "Here's what we plan to do roughly in year two, year three."

I know it's hard to look that far out, but plant the seed with them in terms of where this is going. If you come in at $10,000, even if they want to bring you in and want to spend 100K with you, they have to be able to defend that and now they see a $10,000, it can get really messy, especially because a lot of them are using AI now to understand contracts. So they're going to quickly say, "Oh wait, you spent a thousand dollars with Lenny and now Lenny is asking you for a 100K. Great. Just help me understand why or defend it."

Lenny RachitskyI could totally see ChatGPT being like, "This is interesting."

Jen AbelYeah, exactly.

Lenny RachitskyIt used to be 1K, now it's a 100K. What might be going on here?

Jen AbelTotally. The people don't realize how, again, know the game you're playing and don't be sloppy about it.

Lenny RachitskySo your advice here is really interesting. There's the land to expand. Expand is very important, but the landing may screw your expanding because it sets the wrong reference point.

Jen Abel1,000%. That's exactly right. You said it better than I did.

Lenny RachitskyAnd so you may see in theory if you land a 10K go to 100K, that's an amazing NRR, everyone's going to be really impressed. But you're saying people won't buy into that. It's going to feel absurd and wrong.

Jen AbelUnless it's defendable. All it needs to be is defendable. But who can really defend? That's very hard to defend a 10X. 10X jump, they're going to want to see 15X value.

Lenny RachitskyLet's talk about design partners.

Jen AbelOh yeah.

Lenny RachitskyThis is something most founders try to do. They find a few folks to work with, to help them build the thing. What's your advice on when to start finding design partners? How to find design partners, what a good relationship looks like?

Jen AbelDesign partners are incredible. They're the hardest logos to upsell, meaning go from design partner to full rollout customer. So don't expect these people to be your million dollar pipeline. Expect these people to be the guide, to help you understand, maybe design partners could be a technology company in the Fortune 1,000.

So they're used to experimenting. They're used to technology, they're used to, they were once a startup, so they get it. Those make really good design partners. Most of the design partners that I've closed are usually technology based. They get it and they also are excited about advancing the org and also giving the team an ability to have that startup feel.
So if you're a large massive corporation like Stripe. Stripe doesn't get that startup vibe as much like that 50 person startup vibe, but this can be a gift to give them that lens and give them that voice and give them that excitement that they don't get as a larger company. But those are great types of logos to be early design partners because one, they want to make sure they continue to stay on the cutting edge, but two is they are, to try and build something without that guidance is really, really, really hard because they're not using it.
So you need that user feedback and you also need to tie that to the executive value. It's actually a lot, it's very hard to do, but if you can come out of it and upsell a design partner to a full rollout customer, such a huge win for the market for you, for your team, and also for your investors because it's the hardest customer to actually truly convert.
They've been it when it was messy, they usually got a low price point. But if you again frame it, say, "Listen, I would love for you to be a design partner. I want a little skin in the game to get you to point it. Here's where we want to go and you'll get a discount because you were in the beginning, but I'm setting the framing. Here's where we want to go with pricing. Here's where we are today. You'll always have 30% concession in perpetuity because you are there with us on day one."
So again, it's not about asking for $10,000 and then not expecting that design partner to upsell and keep it flat because there's no growth there. It's a flat. It's about getting that early design partner, set the framing, own the framing and let them know where you're going. Again, a $100,000 to these large logos if they want it, it's very easy for them to get it in.

Lenny RachitskyThere's this really interesting underlying piece of advice of finding a company that pulls you in the direction that leads to success. A company that's kind of a visionary. There's the obvious companies that everyone is always trying to get these days, OpenAI and Anthropic and Stripe I think is one. And any advice for just picking the right early? What are signs that this is a company that will point you in the right direction?

Jen AbelI think they have to be part of a logo that is deemed startup-friendly or in that world, and then I think it's the person, is this person excited to give feedback? Does this person buy in to where we're going? Do they see this world differently like us? Are they in lockstep with the founder vision?

Are they excited to use a tool that's janky? Because it is janky in the beginning, but they know that where this can go can be incredible. So I think it's really about the person and making sure that they're aligned for what they're getting into, and I think a lot of salespeople oversell it. I think that's a common thing that happens and that leads to churn, that leads to frustration, that leads to sometimes just canceling the contract.

Lenny RachitskyThey oversell the initial kind of design partners phase over the product.

Jen AbelThey sell everything. Yeah, design partner, even full rollout, and it's so, so important to tell them, "Here's where we are today. Here's what we cannot do." Which is just as important. It builds trust. "Here's what we will allow you to do in the next six months. Do you want to be on this journey with us? And it's really ugly right now." Right? "Barely anything exists, but we would love your voice to be a part of it."

Lenny RachitskyOne of the biggest fears I think founders have is having a company pull, basically build just for their use case and then it ends up not being used by a lot of people. And so how far do you go fixing their specific problems? Any advice on just how far to go with one company?

Jen AbelThat is the founder's job. The founder's job is to have a clear vision and do not let anything delineate from that. It's important to take feedback in terms of what is the market's reality, but it is the founder, and this is why being a founder is so hard. It is the founder's job to interpret that because a lot of feedback you get is this is the old way, they're responding this way because it's the old way of working.

They want you to build this because that's how they're traditionally expecting to do that. It is not, "Here's where we're going, this is why we're not doing that. I hear you, but here's why we're not going to do that because we're going to completely change the way you do this." That is the founder's job.
And I think we did a bunch of design partnerships late last year and there was a lot of feedback given, a lot of feedback given, but the founder had such clarity with where he wanted to go that he was like 80% noise, 20% had I not asked this question, I wouldn't have gotten that gold in terms of where they are today. And it's that 80/20 rule where 80% of what they're going to tell you is probably going to be not related to where you want to go or based off of the old way, but that 20% of, "Oh, I did not think about it that way." That drives everything.

Lenny RachitskyHave you seen a design partner pull a company in the wrong direction? Just screw their path? Have you seen that or is that pretty rare?

Jen AbelNo, I don't think it's that rare. We hear people complain about it all the time, but I think it's more of an excuse.

Lenny RachitskyComing back to this question of going after the enterprise versus SMBs. And again, early advice you gave is there's no, don't go in between. Either pick SMB small company, which I know you said there's a million ways to differentiate what this means, but I guess I think of employee numbers under some number over a thousand is maybe enterprise. Is that a good way to think about it just like-

Jen AbelYeah, it depends. Are you selling per seats or are you selling based off of usage or are you selling off of, I think it also depends on the pricing model a little bit. I look at headcount too because it's just such an easy way to think about it because you can also gauge usage off that and a bunch of other things, but sometimes the small companies, I think we're going to see a lot more larger companies become smaller because of AI, not significantly smaller, but also high margins allow them to experiment more too.

Lenny RachitskyThat's such an interesting point you're making there that the way we designate enterprise versus SMB like may shift because number of employees may go down with AI.

Jen AbelYeah. Oh yeah.

Lenny RachitskySo interesting. So where I was going to go with this question is when people are deciding, I'm going to go enterprise versus I'm going to sell to startups, like YC companies are the typical example they sell to their own YC batches and you just broad advice of picking, "Okay, we go enterprise versus no, let's actually go startup."

Jen AbelI think it's about, and I read this somewhere and I wholeheartedly agree with it because I've seen it live. I think it's about what game does the founder best understand? Are they an incredible marketer and have some competitive edge for how they can win a massive audience?

I would say go SMB and marketing led or are they a bit more really understand how large corporations work and really excited to deliver on $100,000 plus type of opportunities or the value that they are building for is way more relatable to an enterprise versus a small business.

Lenny RachitskyThat is really interesting. I've never heard of it described that way. I think about linear, which started very startup-ey and my take is they did that because changing the way you work is really hard and their bet was like, "Let's start with companies and grow with them and over time that becomes the default." Any reaction to that?

Jen AbelI think that it sounds like that that's a great way to work because that's a technical tool, so that you need the right, also need to have the right infrastructure to sell. I think Slack, look, Slack and Microsoft Teams are still battling it out at the enterprise. I think it's also how you plug in and how you integrate and do they even have the right systems to support you? The thing with open AI is they didn't have to connect to anything.

Lenny RachitskySay more about that.

Jen AbelSo the value, people were bringing their own use cases to it and it's not like they, well they can ingest and they built that, it's a brand new thing and they started I think, this is someone told me this, so this could be hearsay, but I believe that they were already speaking to CTOs even well before they released to help them explain where this is all going and get their buy-in.

And it's much easier to get into the enterprise when you're like, "We won't even touch your data, won't even touch your data. Just use it to solve problems and then we can build trust and then start to integrate and connect the pipes." But part of the challenges with selling in the enterprise, they're like, "All right, well let's connect all your data in the ..." "Whoa, that's extremely risky."
So you have to start small and low risk, which is like, "Hey, what is the subset of consumers that churned? Let's figure out how we could have made them happier, whatever it be." So that data is lower risk. So again, it's also understanding your market and understanding what their ability to experiment is.

Lenny RachitskyIt's interesting this distinction between OpenAI right now, and Anthropic, I don't know if you've been seeing their growth, it feels like OpenAI is very consumer first and Anthropic is more and more winning on B2B. I saw this chart recently where they're overtaking OpenAI now on B2B. I don't know, any reaction there of just these two different approaches?

Jen AbelI don't because most enterprises I'm talking to mentioned Gemini.

Lenny RachitskyOh, interesting.

Jen AbelOr Microsoft Copilot. So I don't hear much about Anthropic to be honest. So that might be more of a small business startup-ey, I don't know or it's a different part of the organization that's using it.

Lenny RachitskyYeah, that's a whole discussion or bundling right there of Slack and teams and then just Gemini just kind of coming in automatically. People don't have to adopt anything new.

Jen AbelYeah, totally.

Lenny RachitskyThere's something else that you talk about that I love that I don't think people talk much about, which is that enterprise sales is very creative.

Jen AbelOh yes.

Lenny RachitskyTalk about that.

Jen AbelSo I personally believe that small business sales is really a, I used to think it was more science than art. It was more figuring out what didn't work, running experiments, testing and validating, which I do believe, that's to get to foundations, where do we play? What do we want to do? Like that early, early, early zero to one.

From one to 10, I think it's more of an art, which is how do I take my learning and how do I package it up where I own the framing, I can speak to very specific alpha, I can vision cast and where I better understand the problem over time better than the market does. And it's all about deal crafting.
They just need to feel like the value they're getting out of it is way more than the cost. And it's sometimes about giving away things that don't really cost much to you, but are super expensive for them. For example, "Hey, we're selling X tool. We can build out Y specifically for you over the next year and integrate it because I know that you would've spent X number of dollars on engineering resources or you wouldn't have gotten in engineering head internally to do this, but we're just leave it to you. You got to give us a year to build it out."
Again, you're not letting them sidetrack you too much, you're kind of containing it. "We'll do that for you at no additional cost." That's huge value. Right? Or, "Hey, we're going to run an event and we want you at the forefront of it. We want you to be a speaker." Huge value. So it's like all of these additional things that add value beyond just the product but are all part of the product and the vision. Everyone keeps thinking the product is just what goes into their hand.
The product is pricing. The product is the opportunity, the framing and not letting them compare you to something else. And I know we talked that on our first call, which is as soon as you become a comparison, as soon as you become one of three that they're testing out, you've already sort of lost. It's all about differentiation and it's all about here's what you will be able to do tomorrow because of how we're going to serve you today.

Lenny RachitskySo along those lines, it reminds me in our first chat you actually made this point that I've never heard anyone else make, which is that services are a really good way to start getting into the companies that were most founders here. Like, "No, don't do manual stuff for the company. Build a product that you can scale." Your advice is the opposite. Actually start with self-services. Talk about that.

Jen AbelEnterprise is the number one thing they buy services, they know how to do it's super easy, they do it all of the time. It's like the most consistent thing they do. It's their largest budget item, external resources, consultants, whatever.

If they have a very immature way of understanding the problem or they've never purchased technology to solve it to some extent, either one, you are doing something that's never been done before, which is rare in today's day and age, or they might just be laggards on the journey. So you have to decide is this someone you really want to be working with? And if so, selling them as service, even though the technology is powering it on the backend is the fastest way to get your foot in the door.
It's what they know how to buy. Now, the idea is to once you sell that surface, once you get that foot in the door, then it's to guide them towards the product. "Hey, you're spending so much here, why don't we get you to come in and leverage the tool that's been powering this the whole time and move this more into technology serving you versus the human."

Lenny RachitskyWow. I think this will blow a lot of people's minds.

Jen AbelPalantir, this Forward Deployed Engineer, that's exactly what they're doing. There's a lot of companies out, I'm sure OpenAI, and this is what someone told me they were in and talking to CTOs and helping them better understand how AI and their organization can better work together. And it was them coaching them, educating them, whether they did it for free or not, I don't know, but they got their foot in the door, they started to build trust and then it gets adopted.

Lenny RachitskyThis is the epitome of doing things that don't scale that advice we always hear this is like, "Okay, this is what that looks like. We will solve this problem for you. We are using software to do it." And then over time, "Oh, you could just do this yourself. It'll cost you less. You can scale this."

Jen AbelYep, that's right. And they don't even need to know at first that software's doing it. That could be the magic part, which is like, "Guys, we literally, we are literally doing this with our technology."

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There's a lot of talk these days about this idea forward deployed something volunteer was really famous for, just essentially an engineer sitting in your office solving problems with you basically as an employee. And then through that, they learn what software to build. Is that something you're seeing too?

Jen AbelOh yeah, I think that a lot of companies, sorry, a lot of folks that serve the enterprise, they have a butt in a seat in their office. You look at these large consultancies like McKinsey, they're not in their headquarters, they're in their client's office all the time. And the other interesting thing and proof of this is how many people go to a Deloitte or Accenture and expect them to be a channel partner?

This is exactly what this is all about, which is they sell this service, they come in and then they introduce, "Hey, look at what this startup is doing over here. You might want to give them a shot. The problem with channel partnerships and why I don't believe in them is there are a hundred of you on this list and you're expecting them to sell it on your behalf."
Biggest no-no, they're not vision casters, they're not visionaries, they're consultants, but it goes all towards go. I remember startups saying, "Oh, I'm going to go win over Accenture and then have them disseminate me into their clients." And I'm like, as if that's a workable strategy.

Lenny RachitskyOkay. You know what might be helpful is, let me try to summarize some of the best pieces of advice you've shared so far. And this is specifically for folks trying to go from about a million ARR to about 10 million ARR. And then I want to ask you just what's most different about these two stages, but let me share this first. So advice one is go for tier one logos earlier than you think you should because they're early adopters, they can move fast, they can pull you in the right direction.

Jen AbelAnd they excite investors too.

Lenny RachitskyYeah, for sure. And other leads are.

Jen AbelYeah, and other talent, future employees. Yeah, exactly.

Lenny RachitskySo the counterintuitive insight here is you think they will move slow and be too busy, but they are actually the early adopters.

Jen AbelThat's right. They have to maintain that number one spot. And also, all of the people that are in the number two, number three, number four spot, all want to do what number one is doing. So it's also pure referenceability too.

Lenny RachitskyAnd the point about them being the early adopters, the people that join the Stripes in OpenAIs and Anthropics are like they individually love technology and love the latest stuff. So as a human they're like, "Oh, this is cool."

Jen AbelThat's exactly right. I'm just agreeing with myself, that's kind of funny. But yeah,

Lenny RachitskyThat's a good sign. So two is ideally try to price closer to about a 100K, like 75 to 150-ishK is what you said. Most enterprises are used to buying. So instead of starting or even sticking with 10K, 20K for too long, you need to make yourself go towards 75 to 150K.

Jen AbelThat's right, yep. And if you were to sell a service, I know we're talking about selling services first, throw weight that over time, so maybe it's 10K a month. So they start to get used to what that pricing looks like.

Lenny RachitskySo this is a way to make it feel, this is like how you get to 75 to 150K is there's a service attached to it. It's not just, here's my SaaS product, we will solve this problem for you, or a person will be sitting there doing this for you.

Jen AbelOr no, it's the technology too. You can add the services. I always, well let me take that back. Whether the services is bundled into it or not, some people will unbundle it, other people will say the services is a part of it. But yeah, it nets out to 75 to 150K. That's right.

Lenny RachitskyOkay. And you said that it's okay to start lower on ACVs and deals, but you need to push fast towards a 100K over a few months.

Jen AbelYep, that's right. If you can get into an enterprise for 10K in a month, which is not doable, but if you could, and you could go from 10 K to 50 K in four months through an expansion strategy all game, that makes sense, but it's really rare and very hard to do.

Lenny RachitskyAnd so there's two different paths there. One is land cheap and grow quickly. The other is move your ACV average up quickly. Seems like both, the latter is probably the more common strategy is just keep increasing prices.

Jen AbelYeah, because the former you can get tripped up because they could say, "Okay, now give me an economical price for doing this for a hundred people." And then it all kind of evens out because now you're at the 100K deal anyway, but it's much, there's more room for error, which is why I say go in and try to land 100K.

Lenny RachitskyBy the way, in our first chat, we talked a lot about the procurement process, which is what trips a lot of people up and is really painful. And I vividly remember that conversation still. So if people are having issues getting through the sales process and procurement, a lot of good advice there.

Jen AbelAnd getting stuck in procurement is usually because you're not speaking to a senior enough person and they don't know how to navigate it, which is why I'm like that executive needs to be involved because as soon as the executive picks up a phone and tries to get a hold of their buying group, things move.

When people say, "Oh, I'm stuck in procurement." I'm like, "Oh, that could just be a qualification error and you never get out of it because you sold to someone too junior." So that's why the 100K is such a safe zone because even for 10K, you might have to go through procurement. So this is the surest way to make sure that you don't ... Listen, I've seen 10K take nine months to close.

Lenny RachitskyNo bueno.

Jen AbelYeah, so.

Lenny RachitskyOkay. Next piece of advice is this idea of vision casting instead of problem solving. So the advice here is instead of here's your problem, here's how our product solves it is here's how you will achieve alpha in the market by adopting the software. We talked about the example of cursor where if you adopt cursor, you're going to draw the 10X engineers that are joining other companies right now. This will give you a big advantage.

Jen AbelThat's right. And yeah, it's pain versus opportunity, especially in the age of AI, and I know that we're moving into the next dimension. It's all about solving for a gap. It's seldom about solving for a very, very specific problem because people are trying to figure out what's our AI strategy? Where are we going to go with this? What is the world going to look like? I want to be a part of that new world. So it's a great time to be doing that.

Lenny RachitskyAnd then there's a bunch of advice you shared about design partners, of just how to select them. Your advice is definitely have design partners because they will help you build the right thing. But as a founder, you need to have a clear vision and sense of where you want to go and not just build everything they're asking you to build.

Jen AbelThat's right, because important to say no. And that's all part of the framing, which is like here's, we want a little skin in the game. You set the price, but here's what we're marching towards in the next six to 12 months. Are we aligned there? If we deliver on what we say we're going to deliver, are we aligned there and do that kind of handshake?

Lenny RachitskyIs there anything else that I missed that you think is really important for this stage?

Jen AbelSo one to 10 is no longer the founder. Maybe the founder comes in very strategic points, but you need a really good enterprise salespeople. Taking someone from small business and expecting them to do enterprise sales, big no-no, it's a different game, right? Vibe like a different game.

You need to understand how corporations buy. You need to understand how executives think. You need to better understand simply just what the enterprise business model is all about and their ability to take on risk. People will bring in super junior enterprise sales reps and I'm like, "You're looking to sell to an executive and you have this person that's five years out of school with no corporate experience doing it, again, unless they have some extremely deep experience in the industry or are just a unicorn in terms of, wow, this person can sell ice to an Eskimo kind of thing."
A junior person converting an executive, again, if the founder is involved, maybe that's doable, but usually the founder can't be involved in every deal and you need people that can, I always say you need people that can cosplay a founder, which is selling the vision, getting them excited, running through a wall to get the deal done and getting creative on ... None of my deals look exactly the same, every deal looks different and that's okay because every organization has slightly different opportunities of where they want to go, and you have to kind of build towards that and the framing may change.
So it's this ability to adapt from what you're hearing and let that compound over time, but I always say, can this person cosplay the founder? I think that that's the best type of salesperson because it doesn't feel like sales. It's more of the art.

Lenny RachitskyThis is amazing advice. What is a common profile that you've seen be successful? What level of seniority? What kind of personality and any traits to look for?

Jen AbelMaybe a former founder if you can get that, because they're used to selling, they sold investors and they've sold employees. Two is someone with no sales experience, but has deep product experience or an engineer and can think about things in a unique way where the market is like, "Oh, this is so interesting."

Taking a typical salesperson then and putting them into a sales role almost always is where people get frustrated. The market, it feels salesy. The market doesn't want to be sold to, they want to buy. And I know that it's very hard to hire a really good enterprise salesperson. The number of people that I've interviewed, I can count on my hand the ones that I get really, really excited by.
It's almost like coming across a great founder. It's not as common as everyone expects, and I think that that's true for engineering. I think that that's true for sales and I think a lot of people, sales is like, "Oh, just throw a body into it. The product will do the work."

Lenny RachitskyAdvice I often hear is don't hire a senior VP of salesperson from a bigger company. Do you agree with that? What's like to senior?

Jen AbelYeah, so the bigger company thing, the brand was doing all of the work. The brand built the trust. You need this person to be able to build the trust and they're usually, the product is still so new. The product is the founder in the zero to one stage. The product is just starting to get a case study.

You probably have maybe a few references, but it's still very, very early days. You need the market to believe the salesperson and you need that market to know that they're trustworthy. A VP of sales at a large company, I would say, they're best suited for a large company because one to 10, you're running through walls.
You have to figure out, you're doing a lot of convincing, you're doing a lot of educating, you're doing a lot of creative deal crafting. A lot of owning the frame. It's not necessarily selling a product, it's selling that future value, which a VP of sales at a large companies, it's very different. It's a different game. It's kind of like the SMB and enterprise.

Lenny RachitskyIt's interesting you said when you described the profile of a great hire here is you said they don't need to have done sales. If they have done sales, what's a number years or kind of what do you look for that tells you, "Okay, this is a good fit for the first hire."

Jen AbelI actually think it's less about experience and more about the person. Does this person make you feel good? Do you want to buy from this person? I think Jason, Jason Lemkin said that best. Would you want to buy from this person?

Lenny RachitskyCan they sell you a pen?

Jen AbelThe classic. Yeah, exactly. Do they mimic or mirror the market they're selling to? It's much easier to buy from someone that looks and feels like you than it does from somebody that's in a totally different realm. And also, an executive wants to talk to another senior person.

They don't want to talk to someone that just graduated from college and is selling them the new way of working. What do they know? So I think it's tricky. I would say someone with no sales experience makes it feel different and special, that's what I like about it. Someone with sales experience knows how to navigate and probably be qualified better, but it's almost like the blend of those two things.
And that's why I go back to cosplaying the founder, which is like, could this person close a future employee? Do they get excited about the problems they're solving internally and the vision that they get to sell to?

Lenny RachitskyThis actually was a reader question, listener question from Twitter. So Peter Dedenne asked, "How do you make this first salesperson as enthusiastic about the product as you? Is there something you could do? Is it more just they already are and you just leverage that?"

Jen AbelIncentives. Salespeople love to make money.

Lenny RachitskyEasy.

Jen AbelSo if they know it's possible, if they know it's possible, you'll be shocked what people can get done.

Lenny RachitskyIf they see how much they could make. Amazing. I imagine there still also has to be an innate excitement about the product and the opportunity.

Jen AbelThey have to believe in it. They have to believe in the founder, but incentives usually make the world go round, but yeah, is this person, are they asking the right questions to the founder? The best thing to do is have the founder join the first five calls. You know after five calls if this person has what it takes, and don't be afraid to fire. One in every two salespeople usually are fired. Yeah, it's a very high failure rate.

Lenny RachitskyBecause you can tell pretty quickly how it's going.

Jen AbelYou can tell, or the vision of the founders is just very wrong.

Lenny RachitskySpeaking of incentives, do you have any quick advice on how to structure their comp? Just like how much they earn?

Jen AbelIt's usually 50/50. So it's 50% OTE. So it's 50% base salary, 50% OTE.

Lenny RachitskyAnd then how much of the sale do they typically get? Say the first sales hire.

Jen AbelIt depends on the size of the deal, but in technology, it could be anywhere between eight and 12%. So rounds out around 10%.

Lenny RachitskyOkay. Awesome. When do you hire the first salesperson? Is it around the 1 million ARR mark usually?

Jen AbelYeah, it's around that 1 million ARR, mark and I, and it's usually when you have your first seven to 10 customers and there's some pattern recognition around it that you can share with somebody else, there's some consistencies. Otherwise, it's just like that would be very hard.

Lenny RachitskyBasically as a founder, you have to figure out how to sell enough times so that you can show someone, "Here's what's working."

Jen AbelAnd this is the common thing I hear, "Well, I'm a $10 million business. I'm in this small business space. You're $0 in enterprise." It's a zero to one right now in enterprise. It's a totally different game. It's a different value proposition, it's a different deal structuring, it's a different target market. It's a different risk tolerance. It's totally different. So don't be blindsided when-

Lenny RachitskyIt doesn't work.

Jen Abel... There's a lot of unlearning that needs to happen when you move into a new market.

Lenny RachitskySo the advice here is make yourself sell up until around a million ARR, especially if you're trying to go enterprise selling to enterprises yourself as a founder, which is really hard. You have so much to do and you have to be selling this thing for a long time time.

Jen AbelYep. And then try and find someone that you get excited by. It's funny, if you ask the founder, are you excited by your salesperson? I'm curious what the real answer is. It's like, "Well, it's a button to see it in. It was hard to hire, so."

Lenny RachitskyInteresting. I remember, I think it was Jason's advice was to hire two people immediately.

Jen AbelThat's right.

Lenny RachitskySo you can compare them. Do you agree with that?

Jen Abel100%. Yeah, because of the 50% failure rate. I think that's exactly right. So yeah, even a tall order, go find two people that are good. But yeah, I think that that's right because one in two will fail.

Lenny RachitskyOkay, let me ask you another reader question from Hang Huang. This is kind of in a different direction. So he says, "The biggest challenge is always cutting through the noise to get that initial meeting with the right decision maker. How do you even get their attention?"

Jen AbelIt's the vision. What is the opportunity that you're selling? That if they are excited by that, they will take a call. I see it all the time, and don't give away the farm. Keep it to three sentences. And I know I said this on our first call, but say something counterintuitive, they could feel different. Make it feel like they can learn from you by taking a 15-minute call. You see the standards of like, "Oh, I came across your LinkedIn." And, "Are you looking to grow your business by 15%?" It's like, "What kind of statement is that?"

Lenny RachitskyAnd this is in the cold email they get about this pitch.

Jen AbelYeah.

Lenny RachitskyAwesome. So this is a good segue to another reader question from Hugo Alves, Co-Founder of Synthetic users. He asked, "What's the best advice for going from healthy inbound to targeted outbound?"

Jen AbelHealthy inbound usually is a marketing-led initiative. So that's a marketing game. It depends what deal value you're selling. Are you selling a $5,000 deal? It's got to be marketing-led to make the engine work. If you're selling $100,000 deal, you're doing outbound day one. So again, it breaks it into those. This is like that blending of the, I see a blending of that question. This is where you're doing small business marketing-led activities or are you a sales-led organization selling a $100,000 deal?

Lenny RachitskyAnd the reason that's important, just in case it's not obvious, is you're not going to make money if you're selling. People are spending time closing deals that are making 10, 20K. Just the ROI on that won't work for your business model.

Jen AbelThat's right. Yep.

Lenny RachitskyAwesome. By the way, let me just say, Jen, this is an incredible conversation already. We've gone-

Jen AbelOh this awesome.

Lenny Rachitsky... Through so much. This is exactly what I was hoping to get through and we've gone through so much advice that I think is going to be so helpful to so many people. There's a few things that your partner, Justin also suggested I ask you about that I want to touch on. One is you have this question you ask founders a lot that opens up their mind. You ask them, "If you give your product away for free, would people even use this?" And every founder is like, "Of course." And then you ask, "A customer this?" And they're like, "Nah, we wouldn't use this." And that just blows their mind. Talk about just the power of that and how you recommend people approach this.

Jen AbelI always say ask the questions you're afraid to because that truth is going to get you closer and closer to the answer. So I'll ask a client straight up on a call, I'll say, "Honestly, do we think we're going to get the deal done this year? Is it possible?" They'll give you the real answer and people are afraid to ask. But the other side is sort of if they're in it with you, they don't care about that question, right?

Can't ask that question on day one, but if you are, and we didn't talk about this, but maybe this is important. Every single enterprise deal I have done, the deal is done, the deal is closed and pretty much done through text. It's not on email anymore. It is a relationship you're building with someone where if my enterprise client called me, I'm picking up that phone immediately or I'm responding them to immediately because that builds so much trust.
If they know they can call on you, they're going to get you to pick up and they know that you're going to do everything humanly possible to make sure that this is successful. People will turn over rocks for you. I have a client at a Fortune 10 company where I was like, it's so important we get the deal done this year. Is that possible? And she's like, it's a tall order, but if it's going to help you, let's do it.
These are how enterprise deals gets done, it's relationships and it's this, and this is why I'm saying structuring the deal, make it feel like you went to bat for them and in often cases, you are going to bat for them and structure it in a way that makes sense for them. Everyone kind of just tries and pigeonhole. Pigeonholing and deal structuring consistency is important for a $10,000, sub-$10,000 deal. A $100,000 deal, it very commonly will look different every time.

Lenny RachitskyApril Dunford was on the podcast and she shared this really interesting insight that the reason people behave this way is the person at the company buying this thing, their ass is on the line Also, their reputation is on the line for this thing to work out. So they want it to go really well.

Jen AbelThat's right. Again, they do this one in every three years, one in every two years, maybe one in every five years. Hell, I don't know. They don't do this every year. It's very rare. It's no one likes a new tool. No one. Not you, not me, unless it changes everything.

Lenny RachitskyYeah. Figma was a great example, that's Slack.

Jen AbelEverything you've touched

Lenny RachitskyEverything that worked out. You said that you asked these questions that people are afraid to ask. What are some other examples of questions you often ask that people are afraid to ask?

Jen AbelI will say, "Listen, this is $150,000 engagement. I will co-author it with you where we can make this a little bit bigger if you need something else. We can make it a little bit smaller in year one, but in year two it steps up. How do we get this done so when you go to bat, it's a win?" Sell them, do they take it to the wrong side and try and discount you? I've actually never seen that because at that point you have a relationship.

So co-authoring the pricing is so important because they need to know that they go to bat, they can say, "I got this out of them. If we get this deal done." So this is why when I say every deal looks the same, you're asking great questions because it's explaining why I meant by that, but this is another example of why every deal in the enterprise sort of looks somewhat different because a lot of it is co-authored. So again, if someone wants a slightly lower price, give it to them, but maybe them lock them in a little bit longer.

Lenny RachitskyThere's another point that Justin makes that you've touched on a bit, but it's when your no, the way he phrased it is, Jen always talks about how no is the best answer to yes because no is data that you can use. Talk about that.

Jen AbelI am a qualification crazy person. I will not get in on another call with someone because on the first call it's either a yes or a no, there's no in between. Humans are, we're so different and we're so unpredictable, but we're also so predictable at the same time, right? It's very obvious if someone is excited and wants to do something, it is so obvious when someone is just trying to be nice.

So I will say to them on that call, "I'm sort of getting the vibe that this might not be a good fit or might not be good timing. Did I misinterpret that?" And they will usually say, "Yeah, you're right, it's probably not a good fit." And then immediately, "Great, I would love to stay in touch. You've just saved a relationship and you've just saved yourself a ton of time."

Lenny RachitskyAnd the implication here is just to your point, you're limited on time. You don't want to be spending time going down or rival that won't you anywhere.

Jen AbelYeah, exactly.

Lenny RachitskyI'm going to take a quick tangent on tools. What's the state of the art on go-to-market outbound tooling?

Jen AbelI don't use a tool because I believe in the manual and I'll explain why. Every single note I send is slightly different because I see a picture of them and I'm like, "Oh, I don't know if that's going to land." Or I'm like, "Oh, they actually might appreciate this. It's weird." Visual cues are so helpful. A picture is a visual cue, looking at how long they've been in the role, looking how long they've been at the company.

I use all of these little things and I seldom customize a note in a way that people expect which is that first customized sentence because AI does that, and everyone's doing that. So I go the opposite extreme, which is like remove it and I customize it with how I frame it or the subject line. So it's like if I'm talking to someone like a peer, I might say quick question like QQ.
If I'm talking to someone that has a bit more experience, I might write a little bit of a tighter note, not all lowercase. So it just depends on who you're speaking to. And again, this is why it's okay to spend a little bit of time on this because it's a hundred thousand dollars. It's actually a million dollars at the end of the day because a $100,000 deal if you play your cards right turns into a million dollar deal over three to five years.

Lenny RachitskyI love how much you enjoy this. It's so fun to, so essentially what are you doing? You're sitting on LinkedIn finding folks to ping and then you cold email them one individually, manually.

Jen AbelIt's so weird, Lenny, I have no process. I kind of just go with the vibe. I'll read an article about Tesla and I'm like, "Huh, they could be interested in this." Not because that article had anything to do with the problem I'm solving, but because I'm like, "This feels like a good Tesla day." It's hard to describe. It's a very emotional thing for me, and not to toot my own horn, obviously, but I've been successful in sales and the most successful sales people can't explain why they're good at it.

It just comes to them naturally. It's just like an emotional thing. It's like the world's best founders. How do you be a good founder? It's very, very hard to define. How do you become a good engineer? Very, very hard to define. So I don't believe in playbooks. I believe that there's a feel to it. I emailed a chief legal officer at a hedge fund once and he responded to me because I wrote to him on Saturday. I knew it was going to be busy. I made it one sentence and it was tweaked for him.

Lenny RachitskyDo you feel like this is going to be the way as AI SDRs just kind of take over and everyone's getting billions of emails that feel AI-ish?

Jen AbelYes.

Lenny RachitskySo I guess maybe speak more there. Just like is the alpha essentially just become human? Don't automate? Should you think you should?

Jen AbelThe thing about AI tools is they're all pulling from the same databases. So I'm like, "I want to email someone not in the database that's getting hit by a million folks. I want to take a back door in, not the front door where everyone else is trick-or-treating."

Lenny RachitskyAnd this is effective for very large deal, which is what you need to be doing anyway because it takes a lot of time to do it this way.

Jen AbelYeah.

Lenny RachitskyInteresting. So you're not like sitting in Clay, you're not like Apollo, I don't have all those tools. You're just finding people yourself.

Jen AbelYep.

Lenny RachitskyDo you start with a target prospect list at least just like, "Here's the companies that are the perfect fit for this and let's work through them."

Jen AbelIt's all in my brain. I've been doing this for so long, I have in my brain, I'm like, these are my early adopters. These who I'm going to go to after I close those logos, they get excited by those logos. So it's just experience of you land a Walmart, you're going to go to the rest of the industry and say, "Hey, we're working with Walmart." Versus you go to some lower end enterprise company and they're like, "Wait, what do you do?" I can't even comprehend.

Also, the most strategic people, some of the most strategic executives are at these tier one logos. That's why they're tier one because they've got super smart, really capable folks. They also extract the best talent, the best talent likes to experiment and continue to improve. So it's like this compounding thing.

Lenny RachitskyFor someone that isn't Jen and has all this experience, say their founder, they're hit a million ARR. They're just like, "Okay, where do we find our customers?" Do you have any advice for just coming up with who we should go after? Should they be using these tools? Should they be hiring someone like a Jen? I know this is what you do for companies. So one crowd is go hire JJELLYFISH to help them through this.

Jen AbelFounder, the founder. I would say the founder, this is sort of in tune with them in a way. They just have to find it. It's so weird to say it's all, and I hate saying it because it's like a commonplace thing to say, but it's like there's this thing about flow and it's like some of these brands are in flow with you right now, right? You found this insight from somewhere. Who else? What's the next adjacent ring of people that would buy into that?

Lenny RachitskyAnd so what I'm hearing is just pay attention to what's happening, what companies are-

Jen AbelYeah.

Lenny RachitskyThe news, what companies are doing interesting things, who are the kind of early adopters in the market.

Jen AbelIf it was just a database list and it was just about figuring out the right messaging and then emailing folks, we would've known by that by now.

Lenny RachitskyThat's so interesting. Okay, maybe one more question. This again is from Justin. He shares that when you hit resistance, you never argue, you reframe. If someone says, "We already have X solution, you'll agree and pivot and totally X is great for this thing, but here's what we can do."

Jen AbelThis is why it's sell to the alpha. Hey, I know. Listen, that problem you just described, you're right. You have a tool for that. We're taking you much further upstream with value. This is the opportunity I want you guys to have access to.

Lenny RachitskyI love it, Jen. I've gone through everything I was hoping to get through. On the other hand, I feel like we could do another hour on all these things, I feel like we need to do.

Jen AbelWe have three.

Lenny RachitskyYeah, we need round three on the next phase and all the things that people want to dig further into. Before we get to our very exciting lightning round, is there anything else that you wanted to touch on or share?

Jen AbelThis stuff is really hard. It's very hard. Sales is also all about learning very, very quickly from the rejection. The rejection is good because it's a forced learning and you never want to go through that again, but you have to be, I don't like to use the word cringe. You can't be afraid to cringe is like bringing your AI recorder into a call, that's cringey, but sending 15 notes to people that you can deliver serious value to, don't be afraid, and don't be afraid to ask the hard questions. Be different.

The whole game is about, "Oh, this feels different. That's what people want access to." Yet everyone commoditizes themselves. They try and mimic what everyone, they try and mimic a forward deployed engineer. Just rename it. You don't have to use the same nomenclature. Everyone gets excited by the new because the new could be the next thing, the thing that changes it all. So that's why I'm always like, "Don't be better. Be different."

Lenny RachitskyAn amazing way to end it. With that, Jen, we've reached our very exciting lightning round. I've got five questions for you. Are you ready?

Jen AbelYeah.

Lenny RachitskyFirst question, what are two or three books that you find yourself recommending most to other people?

Jen AbelI do Twitter accounts.

Lenny RachitskyOh, Twitter accounts to follow? Oh, amazing.

Jen AbelYeah.

Lenny RachitskyOkay.

Jen AbelLenny, the day I have time to read a book.

Lenny RachitskyPeriod.

Jen AbelPeriod. I would love to be reading books.

Lenny RachitskyCool. Twitter accounts to follow. Tell me.

Jen AbelYeah. Look, obviously you, you produce some of the best content, truthfully,

Lenny RachitskyAppreciate it.

Jen AbelYou get into the minds of people that they're not even giving this insight on Twitter. Who else do I absolutely love? Jason Lemkin. So for sales, Jason Lemkin is awesome, awesome follow for sales, and also he had a great, great recording with you. So link to that because that was a great piece. I actually learned a ton from Matt. I love Gavin Baker. Super nuanced takes. Takes a lot of obvious statements, but shares a lot of the non-obvious insight. He's great. Jason Cohen, have you ever had Jason Cohen on the cast?

Lenny RachitskyJason Cohen, a Smart Bear Jason Cohen?

Jen AbelYeah, yeah, yeah.

Lenny RachitskyHe's coming on the podcast at the end of the year or something.

Jen AbelOh, that's awesome. What a great plug for him right there.

Lenny RachitskyYes.

Jen AbelYeah, those three would be great. I know they're all men, but.

Lenny RachitskyGreat tips.

Jen AbelYeah.

Lenny RachitskyNext question, is there a favorite recent movie or TV show that you've really enjoyed? I know you said you have time to read.

Jen AbelThis is going to be embarrassing, Baywatch.

Lenny RachitskyBaywatch.

Jen AbelYeah. Baywatch channel. It's just so Numby, and it's like '90s classic. Baywatch.

Lenny RachitskyWow, I've never heard that one before. So this is original Baywatch with?

Jen AbelThis is original Hasselhoff. David Hasselhoff.

Lenny RachitskyYeah, Pamela Anderson.

Jen AbelYasmine Bleeth. Pamela Anderson, the original cast.

Lenny RachitskyAmazing.

Jen AbelYeah.

Lenny RachitskyOkay. Deep cut. Is there a product you recently discovered that you really love?

Jen AbelSo the number one thing for me right now is an app called Playground, which is the pictures of my toddler that they upload into the preschool so I can get the daily updates on what's going on in preschool when he's not home.

Lenny RachitskyAmazing. I need that. We get emails and Google Photos. I would really love that.

Jen AbelYeah, there was another one called ClassDojo. There's a few of them, but Playground is the one that this preschool's on.

Lenny RachitskyLove ClassDojo. I'm a small investor.

Jen AbelAre you really?

Lenny RachitskyI am.

Jen AbelOh, that's awesome.

Lenny RachitskyHow about that? Two more questions. Do you have a favorite life motto that you find yourself coming back to find useful in work or in life?

Jen AbelYeah, be direct. Cut the fluff. Give me the bullet, not the paragraph.

Lenny RachitskyFinal question. I was told that by Justin that you've never read a sales book. You've just learned to do this. If you were to read a sales book, if there was someone else out there that you look up to, learn from, is there anyone else out there in the world of sales that you most respect?

Jen AbelI think Jason Lemkin has the strongest understanding of sales. His content is unbelievable. He speaks about it clearly and cleanly, I would say. And as I mentioned, unbelievable Twitter follow. I'm a big fan of his.

Lenny RachitskyAwesome.

Jen AbelI've actually learned a lot from him too. The 50/50 thing or a higher two salespeople, he's spot on. Failure rate is actually probably higher than 50%.

Lenny RachitskyI love that guy. And he's so AI-forward these days. He's just building. He almost took down Replit with his complaints. It was a whole new cycle of how Replit-

Jen AbelHe should interact. Sometimes he says things that are harsh, but you're like, "He's not wrong."

Lenny RachitskyLove it. I got to get him back on the podcast.

Jen AbelYeah.

Lenny RachitskyJen, this was incredible. This was everything I wanted to be. I feel like we just leveled up all the founders that have listened to this in their ability to close. We're going to just create all the economic value and a lot of happy VCs from all the sales that will be closed as a result of the advice you shared. Two final questions. Where can folks find you if they want to either work with you or follow you online? And how can listeners be useful to you?

Jen AbelTwitter. Every new learning or mishap, I put red on Twitter, so it's like my personal diary and super responsive on Twitter DM.

Lenny RachitskyWhat's your Twitter handle? Twitter handle.

Jen AbelIt's double J, So J-J-E-N_A-B-E-L.

Lenny RachitskyYou did not make that easy for people to find you, but we-

Jen AbelYeah, I know, I know, I know I didn't.

Lenny RachitskyAnd the J is for JJELLYFISH, is that where the extra J is for?

Jen AbelYeah, the double Js. Then also, well, someone else had the handle, so I was like, "I need my name."

Lenny RachitskyGot it. By the way, just tell people what JJELLYFISH is in case that might be helpful to them.

Jen AbelYeah, so it's a consultancy that helps folks in the zero to one stage, and now I'm at general manager of enterprise at State Affairs, which is basically giving citizens and corporations an inside peek into what's actually going on inside the state capitol building. State policy is way more impact than on you, than federal policy. Federal policy is written more about.

Lenny RachitskyIncredible. I've only recently learned that that's what you're doing these days, and that is super impactful and important, so thank you for your work there.

Jen AbelEven democracy.

Lenny RachitskyNo big deal. Jen, thank you so much for being here.

Jen AbelThank you so much, Lenny. This was a blast.

Lenny RachitskyBye everyone. Thank you so much for listening. If you found this valuable, you can subscribe to the show on Apple Podcast, 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 lennyspodcast.com. See you in the next episode.

Jen Abel你得先把愿景讲出来。你卖的应该是一个 gap，不是一个 problem。尤其当你面对的是领导者时，你卖的必须是一个机会。市场并不想“被销售”，他们想“主动买”。

Lenny Rachitsky大多数创始人其实宁可拿到 10 个 1 万美元的 deal，也不愿意失去 9 个，只拿下 1 个 10 万美元的 deal。

Jen Abel在特别早期的时候，很多人会无限打折，他们以为这样才是把单子做成的方式。可真正优秀的客户不会这么对你。如果他们一直在那里跟你抠细节、压价格，说明他们并没有真的买入你卖给他们的东西。

Lenny Rachitsky这其实可能会让你对成功和 product-market fit 产生一种虚假的判断。

Jen Abel你一旦变成“对方拿来比价的对象”，一旦你成了他们同时在测的三个供应商之一，你其实已经有点输了。核心就是 differentiation。你要让对方看到的是：因为我们今天会怎样服务你，所以明天你将能做到什么。

Lenny Rachitsky你还提到过一点，就是 enterprise sales 其实是一件很有创造性的事。

Jen Abel它更像一门艺术。核心是 `deal crafting`。你是在跟一个人建立关系。如果对方知道自己可以随时找你，很多人真的会愿意为你去“翻石头”，替你找路。我有一个 Fortune 10 客户，我当时直接跟她说：“我们特别希望今年把这单签下来，这有可能吗？”她回我说：“难度很大，但如果这能帮到你，我们就想办法把它搞定。”很多 enterprise deal 就是这么成的。靠的就是关系。

Lenny Rachitsky那现在 go-to-market 的 outbound tooling，差不多已经发展到什么水平了？

Jen Abel我自己根本不用工具。AI 工具的问题在于，它们大多都在抓同一批数据库。我想发邮件的人，最好是不在那种数据库里、不是每天都被一百万人轰炸的那批人。我想走的是后门，不是所有人都在敲的正门。大家都在正门口敲敲打打、像万圣节挨家挨户要糖一样，我不想跟他们挤在一起。

Lenny Rachitsky今天的嘉宾是 JJELLYFISH 的联合创始人 Jen Abel。她和团队一直在帮助早期创始人学会怎么卖产品，现在她也是 State Affairs 的 Enterprise GM。如果你想把“销售产品”这件事做得更强，这一期会让你大开眼界，而且几乎在每个层面都让你变得更会卖。这是 Jen 第二次来到播客。我们第一次的对话主要聚焦在从 0 到 100 万 ARR，也就是 founder-led sales 那一段。

这一期算是第二部分，聊的是从大约 100 万 ARR 到 1000 万 ARR 的阶段。这可能是你在公开互联网上能免费听到的、最战术、最落地、最深入的一期 enterprise sales 讨论，讲的是到底怎么才能更有效地把产品卖进 enterprise。真的特别期待你听完。如果你喜欢这档播客，别忘了在你常用的播客 App 或 YouTube 上订阅和关注，这会帮到很多。
给你出一道题：OpenAI、Cursor、Perplexity、Vercel、Plaid，以及数百家其他赢家公司，有什么共同点？答案是，它们都跑在今天的赞助商 WorkOS 上。如果你在做面向企业的软件，你大概率已经体会过：单点登录、SCIM、RBAC、审计日志这些大客户要求的能力，接起来到底有多痛苦。WorkOS 把这些会卡单的东西都做成了即插即用的 API，而且是一个专门为 B2B SaaS 打造的现代开发平台。
不管你是想拿下第一个 enterprise 客户的种子轮公司，还是正在全球扩张的独角兽，WorkOS 都是你最快变成 enterprise-ready、打开增长空间的路径。它本质上就像“企业功能版 Stripe”。去 workos.com 就能开始，或者直接去他们的 Slack 支持群，那里有真正的工程师，回复速度非常快。WorkOS 让你像最好的团队那样开发：API 很顺手，文档完整，开发体验也很流畅。去 WorkOS.com，让你的应用今天就具备 enterprise-ready 能力。
本期节目也由 Lovable 赞助。它不只是历史上增长最快的公司之一，我自己也一直在用，而且真的非常推荐。如果你脑子里一直有个 app 点子，但又不知道从哪开始，Lovable 就是给你的。你只要跟 AI 聊天，它就能帮你搭出能用的 app 和网站；之后你还能继续加自动化、再部署到正式域名。它非常适合营销团队快速做工具、产品经理做新点子的原型，也适合创始人去启动下一个业务。
和很多 no-code 工具不同，Lovable 不是做静态页面的，它做的是有真实功能的完整应用，而且速度极快。以前得花几周、几个月甚至几年才能做完的东西，现在一个周末就能跑起来。所以如果你一直压着一个想法没动手，现在就是把它做出来的时候。去 lovable.dev 就能免费开始。Jen，非常感谢你来，欢迎来到播客。

Jen AbelLenny，这种感觉已经越来越熟悉了，而且我挺喜欢的。

Lenny Rachitsky我刚刚应该说“欢迎回到播客”。其实我在 Twitter 上发了你要再来这件事，结果有特别多人提了特别多问题。很明显，大家对这件事既困惑，又特别想学得更好。为了先把讨论框住，我们上一期会放链接，如果有人想从头听，可以从那里开始。上一期聊的是 founder-led sales，本质上是创业最早期、从 0 到大概 100 万 ARR 那一段。

这一期我们要聊的是下一阶段，也就是 enterprise sales 里从大约 100 万 ARR 到 1000 万 ARR，不是 PLG 那条路。你在这件事上有很多很强、也很反直觉的观点和建议。所以我准备直接把这些点一个个拎出来聊，看看最后会走到哪里。开始第一个问题前，你有没有什么更宏观的东西想先说？有什么是你希望大家在 dive in 之前先听到的？

Jen Abel没有，咱们直接进正题吧。

Lenny Rachitsky好。第一个点是，我以前几乎没听别人这么讲过。你经常说：所谓 mid-market，其实并不存在。大家平时当然会提 enterprise，也会提 SMB 和 startups。然后还会有人说，“那我就打 mid-market。”好像是介于两者之间的一个带子。但你不觉得它是个真实存在的分类？讲讲你为什么这么看，大家应该知道什么。

Jen Abel这件事特别有意思。因为如果你让一个人去定义 mid-market，其实你甚至让别人定义 enterprise，每个人都会给出完全不同的答案。有的人按 revenue 分，有的人按 market cap，有的人按员工规模分。而很多人就在这里迷路了，因为卖给一家 100 人的组织，和卖给一家 1000 人的组织，完全是两种不同的游戏，中间并不存在所谓“折中打法”。

所以更好的理解方式是：一边是 small business，这类通常更依赖 marketing 驱动；另一边是 enterprise，通常会是 sales-led。如果你把世界切成这两个非常明确的 silo，就会更容易知道自己到底在打哪一场仗。至于大家说 mid-market，我一般都会反问一句：“你说的是 small business 的上沿，还是 enterprise 的下沿？”
大多数人最后其实说的，都是 enterprise 的下沿。我就会说，很好，那你就要知道自己在打 enterprise game。你要知道该招什么样的人、他们需要多高的 ACV，这样会比你硬造一个“什么都想接一点”的中间地带容易得多。所以我说 mid-market 不存在，因为所谓的 mid-market hire，本质上不是低端 enterprise，就是高端 SMB。你一旦把这两种游戏混着打，你就会输。它们真的差异极大，这就是我的核心理论。

Lenny Rachitsky你之前给我发过一张图，我们之后会放链接。那张图大概展示了不同 segment 里的公司数量，而所谓中间这一段其实几乎没人。你展开讲讲那个图背后的意思。

Jen Abel对，就是这样。它和 power law 很像。你如果去看 Fortune 1000，再往下看 enterprise 的 lower end，数量衰减得非常快。power laws 在大公司世界里其实非常明显，我们不能把所有公司都当成同一种生物来对待。

Lenny Rachitsky那这就会引出一个问题：公司最开始到底该从哪里切进去？传统建议通常是，先从 startups 开始，因为它们更像 early adopters，决策快、动作快；另一边 enterprise 钱多，但周期也长。很多人给的建议是，不要一开始就追那些 fancy 大 logo，因为流程太慢，也容易被搞砸。你的建议是什么？对大多数公司来说，应该从哪里起步？

Jen Abel我给的建议几乎正好相反。真正的 early adopters，往往恰恰就是那些头部 logo。因为它们必须持续留在第一名，所以会不断愿意去尝试新的东西，好让自己继续守住那个位置。其实最难的不是冲到第一，而是一直待在第一。所以那些 Tier 1 logo 往往会想：只要你能给我一点点 alpha，就算只是很小的一点，那都可能成为我升职、被拍肩膀表扬的理由。因为我们是行业第一，我们不能在这里被颠覆。

所以现在有一种很常见的说法，很多 VC 都会讲：“别一开始就打 Tier 1 logo，先下沉去学。”或者说，“先从那些没那么有分量的 logo 开始练。”但恰恰是那些最有分量的 logo，才最愿意试，也最愿意帮你。因为他们同样希望自己能参与塑造你的 roadmap。
当然，什么该做、什么不该做，最后还是 founder 要拍板。但这些客户的声音，真的可以在很短时间内把一笔 10 万美元的 deal 拉成 100 万美元的 deal，它会直接把你往那个方向带。所以当有人说：“先去卖 startups 吧，sales cycle 短。”没错，这我完全理解。决策人更好定义，也不用过 procurement。但在今天这个 AI 时代，一切都在比谁能更快吸走房间里的氧气、谁能更快把 deal 拿下、谁能更快把脚伸进门里，在别人来抢之前站住位置。所以我会说：你得尽可能快地冲到 enterprise。

Lenny Rachitsky为了让大家更好理解，你说的 Tier 1，到底怎么想比较合适？

Jen AbelTier 1 就是像 Walmart、McDonald’s、NVIDIA、Tesla、ExxonMobil、UnitedHealthcare 这种。也就是在自己领域里绝对领先的 logo。它们的工作就是继续待在第一名。

Lenny Rachitsky哇。你的建议真的是非常反直觉，这也正是你今天来这里的价值所在。你的建议是：作为 startup，就应该去打 Chevron、Mobil、Walmart 这种公司。

Jen Abel因为只要你能拿下它们，那就是你最有力的 proof。

Lenny Rachitsky那我们来把这个问题讲得更战术一点。就比如你真的要打 Walmart。虽然我知道这不是一个五秒钟能回答的问题，但如果一个人真想开始卖给 Walmart，他应该怎么去找那个切入口？

Jen Abel第一件事，先确保 founder 亲自上场。大家都喜欢跟 founder 聊，所以先把 founder 尽快推到前台。第二件事，你得会 `vision cast`，你要卖的是一个 `gap`，不是一个 `problem`。`problem selling` 和 `gap selling` 之间差别非常大。`problem selling` 很具体，通常也更技术化，而且几乎所有销售都会默认这么卖：先找问题，再把自己钉在这个问题上。

但你面对的是一位领导者时，你必须在卖愿景，你卖的是一个机会。对方现在在这里，而我们可以把你带到那里。你知道那个图吗？就是 Mario 还没吃蘑菇之前和吃完蘑菇“爆种”之后那张图。大家常说，不要卖蘑菇，要卖 Mario 吃完蘑菇后的状态。其实就是这个意思。
你卖的是机会。这才是能让 Tier 1 logo 真正兴奋起来的东西，也是 founder 最适合卖的东西。卖的是 vision，不是具体 problem。而且这也是让他们愿意“出手试一次”的关键。谁会因为你能解决一个很小的问题，就愿意为你去冒风险、替你去扛呢？他们不会的。

Lenny Rachitsky给个你做过、或者你合作过公司里的例子吧，让这个东西更真实一点。什么样的 `vision cast`，算是做得真的很漂亮？

Jen Abel比如说，我们能给你带来 `alpha`。意思是，我们有一些别人没有的信息、数据，或者一种工作方式。它要么能为你打开一种全新的思考方式，要么能让你以不同方式服务客户，要么能让你用新的方式去解决问题。比如现在，你能接触到的信息层级是这样；而通过我们的资源，或者我们掌握的这类 gated data，我能把你直接往更上游拉，让你更快、更早拿到信息。这有点像高频交易里那“一秒钟优势”的概念。别人当年并不是去卖“我们在铺光纤电缆”，而是卖“我们能比所有人提前一秒给你 alpha”。这种东西，本质上就不是 problem-selling，而是 opportunity-selling。

Lenny Rachitsky我很喜欢你这个说法，“给他们 alpha”。一下就把那种应该带给客户的感觉说明白了。我们之后也会把你说的 Mario 那张图放出来。

Jen Abel你知道那张图？

Lenny Rachitsky知道。最早做出那个表达的人其实是 Kathy Sierra，不知道你还记不记得她。她当年有个特别经典的观点：你不要把 feature 或产品卖给用户，你要卖的是“让他们变成超级英雄”。

Jen Abel对，没错。

Lenny Rachitsky也就是说，你真正卖的是：因为你给他的这个东西，他能变成一个 superhero。而这里说的 vision，其实就是“你会怎样变强”“这个 alpha 会怎样让你更成功”。

Jen Abel这也是为什么 founders 往往特别会卖。因为他们天然会去卖愿景、去做 vision casting；而一个受过传统训练的 salesperson，往往会先找 problem，再照着脚本问问题，整个气氛立刻就死掉了。

听起来就像：“好，你的脚本下一句是什么？”那不是 vision selling，那只是 playbook selling。而在今天这个 AI 时代，很多产品卖的就是 alpha：卖的是速度，卖的是信息获取能力，卖的是 training data。你看市场对这些公司的反应就知道了。它全都是 opportunity，核心全是 alpha。

Lenny Rachitsky那我们再把它说得更具体一点。比如说，Cursor 的销售去卖产品，一个 vision cast 会长什么样？最直接的想法可能是：你的团队会更高效，会比别人更快交付。这个愿景够大吗？

Jen Abel我觉得也许更好的切法是：你将有机会招到那些原本你接触不到的 10X engineer，因为他们就是想用这类工具。也就是说，你能拿到差异化人才。对我来说，我可能会更倾向把话术钉在这里：最顶尖的工程师在用 Cursor。你现在不用。那你想不想拿到这些 10X engineer？

Lenny Rachitsky换句话说，如果你不用 Cursor，他们甚至都不会加入你公司。

Jen Abel对，对。你想想看，其实很多人对自己能不能接受某类工作方式是很挑的。尤其技术人才，我自己不是技术背景，但我完全能想象，他们并不愿意去那些大公司，只因为进去之后还得被迫用某些老旧的 incumbent 工具。

Lenny Rachitsky继续回到“打大公司”这件事。我问了你的同事 Justin，他觉得你做的最能影响团队 sales success 的事情是什么。他提了很多点，我后面会一个个问，但其中一个是：大多数 founder 在开大 ACV、或者说敢不敢收大单这件事上，其实是没有安全感的。用他的原话来说，就是大多数 founder 宁可拿 10 个 1 万美元的单，也不愿意丢掉 9 个，只拿下 1 个 10 万美元的单。聊聊你在这件事上的建议，以及你看到的问题。

Jen Abel特别早期的时候，很多人为了做成 deal，会一路打折打到底，因为他们觉得这才是“把单签下来”的方法。但真正好的客户不会这么对你，因为这本身就是一个 qualification signal。如果对方一直在那里跟你讨价还价，说“我不觉得它值这个价，我不觉得它值那个价”，那说明他们并没有真的 fully bought in。

所以当我说“我宁可要一个 10 万美元的 deal，也不要 10 个 1 万美元的 deal”时，我真正想说的是：我宁可只有一个 rock star client，它能帮我一起摸清下一阶段产品该往哪走，也不要 10 个客户里，5 个还不错、5 个完全不适合，而那 5 个不适合的我还得花资源去服务，最后只会分散我的注意力。这也是为什么我特别喜欢 enterprise sales。因为他们不会轻易把你带进来，除非这件事对他们真的重要，或者更准确地说，它会以一种他们愿意确保它成功的方式去影响他们。这就是我喜欢 enterprise sales 的地方。
他们有足够的资源去确保这个东西被真正落地。因为今天这个时代，如果一个工具没人用，最后它就会被砍掉。所以他们会非常在意：自己带进来的东西、自己替它去扛的东西，一定要真的成功。别忘了，他们可能两年才会替某个新东西站一次台，最多三年一次。你必须让这件事感觉“值到爆”，感觉像它会让自己变成一个超级英雄。
否则还有什么意义？enterprise 组织今天之所以会把采购流程设计得那么难，就是因为它们想确保：你带进来的东西，是你真的、真的特别想要的。这个系统会自动把“也许挺不错”的那种 mediocre 东西挡掉，只留下那种“这会改变我们的工作方式”“这会影响我们获取某种 alpha 的能力”的产品。正因为这样，它才会 sticky。

Lenny Rachitsky所以你这里更宽泛的建议是：不要太在意那些 1 万美元级别的小机会。原因有几个。第一，它们可能会给你一种虚假的成功感，甚至让你误判 product-market fit。第二，这类公司未必足够有前瞻性，反而不能把你带去对的方向。第三，它们大概率还会逼你打折，把你的 pricing 体系也打乱。

Jen Abel对，而且再补一条：1 万美元这种单子，不太会让别人真正认真看待你。10 万美元的 deal 才会。因为 10 万美元的单更难做，必须得有 executive sponsor 进来。我宁可多花两个月把 deal 做成，但最后是有 executive 真正签字背书的。因为那说明对方是真的买入了。接下来你就能跟他们一起明确：他们到底想解锁什么价值？甚至你还有机会把那位 executive 自己变成用户。而在今天这个时代，我们这一代人已经开始成为这些大公司的高管了，这类工具对他们来说是原生的。

Lenny Rachitsky那这套建议适用于谁？你的意思是不是，只要想做成一家真正成功的 B2B 公司，大家最后都应该瞄准 10 万美元这一档的 deal？还是说，也有一些公司能靠 1 万美元的单打很久，并且依然成功？

Jen Abel如果你的 win rate 高到离谱，而且市场又足够大，那当然也不是绝对不行。因为最后你只是在反推数学：如果你想做到 1 亿美元收入，那你到底需要多少个 1 万美元 deal？而且 1 万美元 deal 的扩展空间也摆在那里。你最多从 1 万长到 1.5 万，这已经是 50% 增长了；可从 10 万长到 50 万，反而容易得多，因为对方只要想多给更多 seats，或者想从你这里拿更多 value，就能往上推。

对 enterprise 来说，他们天然就更愿意从一个已经信任的 existing vendor 身上拿更多东西。所以这也跟你是哪种类型的公司有关。如果你是 venture-backed 的，你不可能靠给 enterprise 卖 1 万美元 deal 活下来，你会被直接打死。或者更准确地说，你从一开始就已经输了，因为你在 enterprise 赛道里打的是一套 small business game。

Lenny Rachitsky你服务过的公司里，有没有真的在 1 万、2 万美元这个 bucket 里做得不错的？还是说这种情况其实非常少？

Jen Abel前提是他们卖的是 enterprise 吗？

Lenny Rachitsky对。

Jen Abel有，但那种情况一般是前三个月先从小单切进去，然后很快从 1 万涨到 5 万，再涨到 10 万，扩张速度很快。这样我觉得合理。你先把脚伸进门里，然后再健康地指数式扩出去，这没问题。但如果是一年 1 万，下一年 1.2 万，再下一年 1.5 万，那这数学迟早会崩。

Lenny Rachitsky这太好了。我感觉很多 founder 听到这里，心里一定在想：“不不不，我们可能就是那个例外。1 万起步，慢慢做到 2 万也行啊。上来就想 10 万，太夸张了吧。”

Jen Abel不会的，数学会先把你打醒。而且，真正厉害的 salesperson，如果佣金对应的只是 1 万美元单子，你是招不到最好的人的。厉害的销售会想的是：我怎么卖出一笔 25 万美元 deal？怎么卖出半百万 deal？你想要的，应该是这种人。

Lenny Rachitsky而这里面有一个很重要的 lens，是它会反过来逼你去打造那种本来就能卖到 10 万、50 万的产品。

Jen Abel对，完全是这样。归根到底，这就是 enterprise game。如果你本来走的是 small business 路线，但某天一个 enterprise 公司主动来找你，说：“我们挺喜欢这个，你能不能给我们三个 seat？”这时你千万要按 enterprise 的方式去 structuring。不要拿 small business 的打法去接 enterprise 客户。

Lenny Rachitsky展开讲讲。什么叫“不要用 small business 的方式卖给 enterprise”？

Jen Abel比如你是 PLG，突然像 Walmart 这样的公司来找你，说：“我们能不能先给三个用户开通一下？”很多 founder 会瞬间兴奋到不行，然后直接按 small business pricing 卖给 Walmart 三个 seat。可一旦这么卖了，后面要再把这三个人的合同拉到 10 万美元，会变得非常非常难。因为现在文档上已经明确写着，他们最初为这东西付了多少钱。

Lenny Rachitsky所以这里真正的问题是，初始价格一旦定错，后面真的会把你坑惨。显然我们不可能在这里把整套定价策略讲死，但你的建议是直接把价格定高一点吗？还是你会怎么做？

Jen Abel企业客户对“先落地、后扩张”这套其实很熟，最初的合同大概落在 7.5 万到 15 万美元之间，他们并不陌生。事实上，这往往就是你最该从这里起步的区间，因为你还得知道这单后面还能长到哪里。先把范围收住，别一上来就说 15 万，然后把整块业务全卖掉。你要讲清楚的是：这是 15 万，谁能用，能交付什么价值，以及接下来会怎么演进。你还要让他们知道，我们大概会在第二年、第三年做什么。

我知道看那么远很难，但你得先把这颗种子种下去，让对方明白这条路会通向哪里。要是你一上来只收 1 万美元，就算他们原本想和你做到 10 万，也得先替这个价格找理由。现在很多人还会用 AI 去审合同，所以他们很快就会问：等等，你去年和 Lenny 只花了 1000 美元，现在却要 10 万？那你得解释清楚，证明这个跳涨是合理的。

Lenny Rachitsky我完全能想象 ChatGPT 会说：“这事挺有意思的。”

Jen Abel对，没错。

Lenny Rachitsky它之前还是 1K，现在一下变成 10 万。中间到底发生了什么？

Jen Abel没错。很多人都没意识到，你得先搞清楚自己在打什么游戏，动作别太粗糙。

Lenny Rachitsky这点很有意思，我以前从没听人这么讲过。我会想到 Linear，它一开始就很“startup 味”，我的理解是，他们这么做是因为改变工作方式真的很难，所以他们的下注逻辑是：先从一些公司切进去，跟着他们一起长大，慢慢变成默认选项。你怎么看？

Jen Abel我觉得这种路径很合理，因为这本身就是个技术工具，所以你得有合适的销售基础设施。Slack 和 Microsoft Teams 到现在还在 enterprise 里打得难解难分。关键也在于你怎么接入、怎么集成，以及你的系统到底能不能支撑你。OpenAI 的情况就不一样，它一开始根本不需要接任何东西。

Lenny Rachitsky展开说说。

Jen Abel它的价值是用户把自己的使用场景带进来，而不是它先去硬接一堆系统。它当然后来也能接入、能 ingest、能做这些，但那是后来的事。它本质上是一个全新的东西。我听别人说，他们在正式发布之前，其实很早就已经开始跟 CTO 们沟通，帮他们理解这件事到底会往哪里走，并争取他们的 buy-in。这个我没法完全确认，算是听来的，但我相信大概率是真的。

而且，如果你一上来就说：“我们连你的数据都不会碰，真的一丁点都不会碰。你先拿去解决问题，等信任建立起来了，我们再慢慢做集成，把管道接起来。”那进入 enterprise 会容易很多。enterprise 销售最难的地方之一，就是对方会说：“好，那我们把你们所有数据都接进来吧……” 这时候你就得立刻警觉：“哇，这风险非常高。”
所以你必须从小处、低风险的场景开始。比如：“好，我们先看一小撮流失掉的用户是谁，想想当时怎么做能让他们更满意。” 这种数据风险就低很多。说到底，还是得理解你的市场，理解对方到底有多大试错空间。

Lenny RachitskyOpenAI 和 Anthropic 现在的差异也挺有意思的。我不知道你有没有观察到他们的增长轨迹，感觉 OpenAI 更偏 consumer first，而 Anthropic 越来越像是在 B2B 上赢。我前阵子还看到一张图，说他们现在在 B2B 上已经要超过 OpenAI 了。你对这两种路径有什么看法？

Jen Abel我其实没什么感觉，因为我聊的大多数 enterprise 客户，提到的都是 Gemini。

Lenny Rachitsky哦，有意思。

Jen Abel或者 Microsoft Copilot。所以坦白说，我很少听到他们提 Anthropic。那可能更偏 small business、startup 那一侧，或者是组织里别的部门在用。

Lenny Rachitsky对，这里面其实就是另一整套讨论了，Slack 和 Teams 的 bundling 也是一样。再加上 Gemini 直接顺手就进来了，用户甚至不用再学一个新东西。

Jen Abel对，完全是。

Lenny Rachitsky你还提过一个我特别喜欢、但我觉得大家很少聊的点，就是 enterprise sales 其实非常有创造性。

Jen Abel没错。

Lenny Rachitsky讲讲这个。

Jen Abel我个人一直觉得，小企业销售我以前会觉得它更像科学，不像艺术。更多是在找哪些方法不行、做实验、测试、验证——这些我当然也认同，因为那是打基础：我们到底在哪儿打、我们到底想做什么，那种早期的 zero to one 阶段。

但到了 one to ten，我觉得它更像艺术，核心是我怎么把自己学到的东西打包起来，既把 framing 抓在自己手里，又能讲出非常具体的 alpha，还能做 vision cast，而且随着时间推移，我对问题的理解会比市场更深。这一切都绕不开 `deal crafting`。
对方只需要感觉到，他们拿到的价值远远超过成本就行。有时候这意味着你要送一些对你来说成本不高、但对他们特别贵的东西。比如说：“我们在卖 X 工具，我们可以在接下来一年里专门为你做出 Y 并把它集成进去，因为我知道你本来得花一大笔工程资源，或者根本找不到内部工程能力去做这件事。我们来替你做，但你得给我们一年时间把它做出来。”
而且你还不能让他们把你带跑偏太多，你要把范围控制住。你可以说：“这部分我们可以免费帮你做。” 这就是巨大的价值。又比如：“我们会办一场活动，希望你站在最前面发言。” 这也是巨大价值。所以这些额外的东西，其实都在给产品加值，而它们本身也都属于产品和愿景的一部分。很多人总觉得产品只是他们拿到手里的那个东西。
但产品还包括定价、机会、 framing，以及不让对方拿你去和别的方案对比。我在第一次聊天里也讲过这一点：你一旦变成了对方拿来比较的对象，一旦成了他们在测的三个方案之一，你基本就已经输了。核心永远是 differentiation，核心永远是：因为我们今天怎么服务你，所以你明天能做成什么。

Lenny Rachitsky顺着这个说，我想起我们第一次聊时，你提过一个我从没听别人讲过的观点：services 其实是进入那些公司的一条很好的路。大多数 founder 听到这都会说：“不行，别给公司做手工活，赶紧做成可以规模化的产品。”你的建议正好相反，你说应该先从服务做起。讲讲这个。

Jen Abelenterprise 最常买的就是服务，他们很熟，也很容易买，几乎天天都在买。这是他们最稳定的支出项之一：外部资源、顾问之类的。要是他们对问题的理解还很不成熟，或者压根没买过技术去解决这个问题，二者要么意味着你在做一件前所未有的事——这在今天已经很少见了，要么就说明他们只是这条路上的落后者。

所以你得先判断：这个客户是不是你真的想长期合作的人。如果是，那把你的技术包在服务里卖出去，虽然后台还是技术在驱动，但这是最快把脚伸进门里的办法。因为这就是他们知道该怎么买的东西。
而真正的思路是：当你卖出这个 service、当你先把门打开之后，再慢慢把他们往产品上引。“你们现在在这里花了这么多钱，不如直接把这套一直在背后驱动服务的工具用起来，慢慢把事情从人力服务转回技术来承接。”

Lenny Rachitsky哇，我觉得这会把很多人的认知直接掀翻。

Jen AbelPalantir 的 `Forward Deployed Engineer`，本质上就是在做这个。很多公司都是这样，OpenAI 也是，我听说他们早就开始接触 CTO，帮他们更好地理解 AI 和组织该怎么协同工作。你可以把它理解成 coaching、education，不管是不是免费，我不知道，但他们确实先把脚伸进门里了，先建立了信任，然后产品才慢慢被采纳。

Lenny Rachitsky这简直就是“做那些不规模化的事”这句建议的典型案例。它的意思就是：好，我们就是先替你把这个问题解决了，但我们背后用的是软件。等过一段时间，你就会发现：“哦，原来这事你自己也能做，而且成本更低，还更容易扩展。”

Jen Abel对，就是这样。而且一开始他们甚至不用知道背后是软件在做。那可能就是最妙的地方——“各位，其实我们就是在用自己的技术做这件事。”

Lenny Rachitsky今天这期节目由 Coda 赞助。我自己每天都在用 Coda 来管理播客，也用它来管理社区。我要问每位嘉宾的问题都放在里面，社区资源也放在里面，工作流也是靠它在跑。

Coda 能怎么帮到你？想象一下你在工作里启动一个项目，愿景已经很清晰，你知道每个人该做什么，也知道自己需要去哪儿找数据。你甚至不用浪费时间到处搜，因为团队需要的东西，从项目看板、OKR 到文档和表格，全都在 Coda 的一个页面里。Coda 这个协作式的一体化工作区，把文档的灵活性、表格的结构、应用的能力和 AI 的智能都放在同一个易于整理的页面里。
我前面也说过，我每天都在用 Coda。超过 5 万支团队也信任它来保持一致和专注。如果你是想提升对齐效率和执行速度的 startup 团队，Coda 可以帮你把计划到落地的节奏大幅缩短。去 coda.io/lenny 就能免费试用，还能拿到创业团队方案 6 个月免费，网址是 C-O-D-A.io/lenny。
最近有很多人都在聊一种“前置部署”的角色，也就是某种工程师直接坐进你办公室，像员工一样一起解决问题，顺便再反推该做什么软件。你也看到这种趋势了吗？

Jen Abel当然。很多服务 enterprise 的团队，本质上就是把人放进了客户办公室。你看 McKinsey 这种大咨询公司，他们根本不在自己总部待着，几乎总是在客户办公室里。还有一个很有意思的证明，就是有多少人去 Deloitte 或 Accenture，还默认他们会帮自己做 channel partner？

这其实就是这个逻辑：他们先卖服务，进场之后再说，“看，这家 startup 在做这个，你可以试试。” 但我不太相信 channel partnership，核心原因是：名单上有一百个你，大家还都指望他们替你卖，这怎么可能。
这就是最大的问题。他们不是 vision caster，也不是 visionary，他们是 consultant，但这件事一路都在往前推。我记得有 startup 跟我说：“我们要先拿下 Accenture，再让他们把我们分发给自己的客户。” 我当时就想，这怎么可能是一套可行策略。

Lenny Rachitsky好，我先试着总结一下你到目前为止讲得最好的几条建议。这一段是专门给那些想从大约 100 万 ARR 走到 1000 万 ARR 的人听的。然后我想再问你，这两个阶段最不一样的地方到底是什么。但我先总结一下。第一条建议是，比你想象得更早去打 Tier 1 logo，因为他们就是 early adopters，跑得快，还能把你往对的方向拉。

Jen Abel而且他们也会让投资人兴奋。

Lenny Rachitsky对，没错。也会吸引别的潜在客户。

Jen Abel对，也会吸引人才，未来的员工。完全是这样。

Lenny Rachitsky所以这里最反直觉的点就在于：你以为他们会很慢、很忙、没空理你，但实际上他们反而才是最早愿意试的那批人。

Jen Abel对，没错。他们必须守住第一名的位置。而且，排在第二、第三、第四的人，也都想做第一名正在做的事。所以这件事本身也特别有参考价值。

Lenny Rachitsky还有你说他们是早期采用者这点。加入 Stripe、OpenAI、Anthropic 的那些人，很多本身就特别喜欢技术，也喜欢最新的东西。所以从人的角度看，他们会觉得，“哦，这个很酷”。

Jen Abel没错，完全是这样。我这是在自己附和自己，听起来有点好笑，不过对。

Lenny Rachitsky这就是个好信号。所以第二点最好是尽量把价格往 10 万美元附近靠，像你说的，7.5 万到 15 万美元左右。大多数 enterprise 都习惯这么买。别一开始就定 1 万、2 万，然后还在那个区间里待太久，你得逼着自己往 7.5 万到 15 万走。

Jen Abel对，没错。如果你卖的是服务，我知道我们前面在说先卖服务，那就随着时间把价格往上抬，比如每月 1 万美元。这样他们就会慢慢习惯这个价格长什么样。

Lenny Rachitsky所以这其实是在把价格推到 7.5 万到 15 万的办法，就是把服务绑进去。不是单纯地说“这是我的 SaaS 产品，我们帮你解决这个问题”，或者“会有一个人坐在那儿替你做这件事”。

Jen Abel也不是，它还是技术在起作用，你可以把服务加进去。让我收回刚才那句话。不管服务是打包进去还是单独拆出来，有些人会把它拆开卖，有些人会说服务就是产品的一部分。总之，最后的结果就是 7.5 万到 15 万美元，这没错。

Lenny Rachitsky明白。你还说了，ACV 和 deal 的起步可以低一点，但得在几个月内很快推到 10 万美元。

Jen Abel对，没错。如果你能在一个月内以 1 万美元切进 enterprise，虽然现实里几乎做不到，但如果真能做到，而且能在四个月里通过扩张策略把它从 1 万推到 5 万，那就说得通，不过这真的很少见，也非常难做。

Lenny Rachitsky所以这里其实有两条路。一条是先低价切入，再快速增长。另一条是尽快把平均 ACV 往上抬。看起来两条都行，但后者大概更常见，就是不断涨价。

Jen Abel对，因为前一种很容易出岔子。对方可能会说：“好，那你给我一个按 100 个人来做的经济型价格。” 这样一来，最后算下来其实还是 10 万美元的单，只是中间更容易出错，所以我才说，进去就尽量把单子落在 10 万美元。

Lenny Rachitsky顺带一提，我们上次聊了很多采购流程，那正是很多人卡住、而且特别痛苦的地方。我到现在都还记得那段对话。所以如果大家在销售流程和采购上遇到问题，那里有很多很好的建议。

Jen Abel采购卡住，通常是因为你没有跟足够 senior 的人说话，而对方也不知道怎么往下推进。所以我才一直说，executive 必须参与进来，因为只要高管拿起电话，试着联系他们自己的采购团队，事情就会动起来。

别人一说“我卡在 procurement 里了”，我就会想，这可能只是一个 qualification 失误，因为你卖给了太 junior 的人，所以永远出不来。这也是为什么 10 万美元是一个很安全的区间，因为就算是 1 万美元的单子，你也可能得走采购流程。所以这才是最稳妥的方式，能尽量避免……说真的，我见过 1 万美元的单子拖九个月才签下来。

Lenny Rachitsky太难受了。

Jen Abel对，所以……

Lenny Rachitsky好，下一条建议是 vision casting，而不是 problem solving。也就是说，不要按“这是你的问题，这是我们的产品怎么解决它”来讲，而是要讲“你通过采用这个软件，怎样在市场里拿到 alpha”。我们前面举过 Cursor 的例子：如果你用 Cursor，你就更容易吸引那些现在正在加入别家公司的 10X engineer。这会给你很大的优势。

Jen Abel对，就是这样。而且这讲的是 pain versus opportunity，尤其在 AI 时代，我知道我们已经在进入下一个维度了。核心是去解决一个 gap，而很少是去解决一个特别具体、特别细的小问题，因为大家都在琢磨：我们的 AI strategy 是什么？我们要往哪儿走？这个世界会变成什么样？我想成为那个新世界的一部分。所以现在正是做这件事的好时候。

Lenny Rachitsky然后你还分享了很多关于 design partner 的建议，主要是怎么选。你的建议当然是要有 design partner，因为他们能帮你做对东西。但作为 founder，你必须有清晰的愿景和方向感，不能对方提什么你就全都照着做。

Jen Abel对，学会说不很重要。这个也属于 framing 的一部分，就是说我们希望你先投入一点 skin in the game。价格可以你来定，但我们接下来六到十二个月是要往哪儿走，这一点我们要先对齐。如果我们真的交付了自己承诺的东西，那我们是不是都认同这个方向？这种握手式的共识很重要。

Lenny Rachitsky还有别的我漏掉的吗？你觉得对这个阶段特别重要的东西。

Jen Abel一到十这阶段，已经不能再靠 founder 亲自一个人撑着了。也许 founder 会在几个特别关键的节点介入，但你需要非常强的 enterprise salesperson。把一个只做过 small business 的人拉过来，然后指望他做 enterprise sales，这绝对不行，这是完全不同的游戏，真的，整体气质都不一样。

你得理解大公司是怎么买东西的。你得理解高管是怎么想问题的。你还得更深地理解 enterprise 的商业模式，以及他们对风险的承受能力。很多人会招很 junior 的 enterprise sales rep，我就会想：你是要卖给一个 executive，结果派了一个刚毕业五年、没有任何 corporate 经验的人去做，除非这个人对行业有特别深的理解，或者真的是个怪物级天才，像“这人居然能把冰卖给爱斯基摩人”那种。
一个 junior 去转化 executive，除非 founder 亲自参与，否则通常很难做到。但 founder 也不可能每个单子都亲自上，所以你需要那种能 cosplay founder 的人。我的意思是，他得会卖愿景，能把人点燃，能为了把单子拿下去撞墙，也能在 deal crafting 上很有创意。我的单子没有一单是完全一样的，每单都不同，这没问题，因为每个组织想去的方向都会稍有不同，你得顺着那个方向把故事搭起来，framing 也会变。
所以关键是，你能不能根据自己听到的信息不断调整，并让这些经验随着时间累积起来。但我总会问：这个人能不能 cosplay founder？我觉得这才是最好的 salesperson，因为它不会让人感觉像在卖东西，更像是一门艺术。

Lenny Rachitsky这真的是很棒的建议。那你看到过的、比较常见的成功画像是什么？通常是什么资历、什么性格、什么特质？

Jen Abel如果能找到前 founder，那可能很好，因为他们本来就习惯卖东西，卖过投资人，也卖过员工。第二种是没什么 sales 经验，但有很深的产品经验，或者本身就是工程师，能用一种独特的方式去思考，这样市场会觉得，“哦，这很有意思”。

把一个传统 sales 直接扔去做销售，几乎总会让人很挫败。市场会觉得太 salesy 了。市场不想被“卖”，他们想买。我也知道，要招到一个真正厉害的 enterprise salesperson 非常难。我面试过的人很多，真正让我眼前一亮的，掰着手指头都数得过来。
这就像遇到一个好 founder，一样没那么常见。我觉得工程师也是这样，sales 也是这样。我觉得很多人总觉得 sales 很简单，随便扔个人进去，产品自己会搞定。

Lenny Rachitsky我经常听到的建议是，不要从大公司挖一个高级 VP of Sales。你同意吗？你觉得“太 senior”是个什么概念？

Jen Abel对，大公司那种情况，品牌本身已经帮忙干了很多活，信任是品牌建立的。你需要的是一个能自己建立信任的人，而通常这时候产品还很新。产品在 zero to one 阶段，其实就相当于 founder 本身，顶多才刚开始有 case study。

你可能有几个 reference，但整体还是非常早期。你需要市场相信这个 salesperson，而且要知道他是值得信任的。大公司的 VP of Sales，我会说他们更适合大公司，因为在一到十阶段，你是在不停撞墙。
你得做大量说服、大量教育、大量创意型 deal crafting，还得很会掌控 framing。卖的不一定是产品本身，而是未来的价值。大公司的 VP of Sales 跟这个是很不一样的。这是另一种游戏，跟 SMB 和 enterprise 的区别很像。

Lenny Rachitsky你在描述一个好 hire 的画像时，说过一个很有意思的点，就是这个人不一定非得做过 sales。如果做过 sales，你会看什么样的年限，或者什么样的信号，能让你觉得“好，这人很适合做第一位销售”？

Jen Abel我其实觉得，这跟经验没那么相关，更多是看这个人本身。这个人会不会让你感觉舒服？你会不会想从他那里买东西？我觉得 Jason Lemkin 说得最好：你愿不愿意买这个人的东西？

Lenny Rachitsky他能卖你一支笔吗？

Jen Abel经典问题，对，就是这个。这个人是不是跟他要卖的市场很像？从一个看起来、感觉起来都像你的人那里买东西，总是比从一个完全不在一个世界的人那里买更容易。而且高管也想跟另一个 senior person 说话。

他们不想跟一个刚大学毕业、来给自己推“新工作方式”的人聊天。他们会想：你知道什么？所以这里挺微妙的。我会说，没有 sales 经验的人，会让这件事显得不一样，也更特别，这点我很喜欢。有 sales 经验的人，通常更会 navigate，也更会做资格判断，但最好的其实是这两者的结合。
所以我又回到那个说法：能不能 cosplay founder？也就是，这个人能不能把一个未来的员工都招进来？他会不会因为自己内部要解决的问题，以及自己要卖出去的愿景，而真的兴奋起来？

Lenny Rachitsky这个其实也是 Twitter 上一个听众的问题。Peter Dedenne 问：“你怎么让这个第一位 salesperson 跟你一样对产品充满热情？你会做些什么，还是说他们本来就这样，你只是利用这种热情？”

Jen Abel激励。salespeople 最爱赚钱。

Lenny Rachitsky简单。

Jen Abel所以如果他们知道这件事能赚钱，如果他们真的知道能赚到钱，你会惊讶于人能把事情做到什么程度。

Lenny Rachitsky如果他们看到了自己能赚多少钱，效果会很惊人。我猜这里面还是得有一种对产品和机会的本能兴奋感。

Jen Abel他们必须相信这件事。他们必须相信 founder。但激励通常才是让世界运转的东西。不过说到底，这个人是不是在问 founder 正确的问题？最好的做法是让 founder 参加最开始的五次通话。你只要开完五次会，就知道这个人有没有料了。别害怕开人。做销售的人里，大概有一半最后都会被开掉。对，失败率非常高。

Lenny Rachitsky因为你很快就能看出进展到底怎样。

Jen Abel对，能看出来，或者 founder 的愿景本身就错了。

Lenny Rachitsky说到激励，你有没有快速建议，怎么设计他们的薪酬包？就是他们大概怎么拿钱。

Jen Abel通常是五五开。也就是 50% OTE，50% base salary，50% OTE。

Lenny Rachitsky那他们通常能拿到这单里多少提成？比如第一位 sales hire。

Jen Abel要看 deal 的大小，但在科技行业里，通常会在 8% 到 12% 之间，平均下来差不多 10%。

Lenny Rachitsky明白了。很棒。你一般什么时候招第一位 salesperson？通常是在 100 万 ARR 左右吗？

Jen Abel对，通常就是 100 万 ARR 左右。而且一般是你已经有了前 7 到 10 个客户，并且开始能看出一些 pattern，能把这些共性讲给别人听。也就是说，你已经能提炼出一些一致性了。不然的话，这事会非常难。

Lenny Rachitsky基本上作为 founder，你得先把销售这件事自己做足够多次，才能告诉别人：“这就是有效的做法。”

Jen Abel我经常听到的一个说法是：“我是一个 1000 万美元的企业，我在 small business 这个赛道里做得很好。你们 enterprise 还是 0。” 但 enterprise 现在其实还是从 0 到 1，完全是另一回事。价值主张不一样，deal structuring 不一样，目标市场不一样，风险偏好也不一样。真的完全不同，所以别到时候措手不及——

Lenny Rachitsky结果就是不灵。

Jen Abel……你进入新市场时，要重新学的东西很多。

Lenny Rachitsky所以这里的建议就是，尽量让自己一直卖到差不多 100 万 ARR，尤其是如果你打算自己作为 founder 去卖 enterprise，那真的很难。你有太多别的事要做，还得长期一直卖这个东西。

Jen Abel对。然后再去找一个让你真的兴奋的人。挺有意思的是，如果你问 founder：“你对你的 salesperson 兴奋吗？”我很好奇真实答案会是什么。很多时候会变成：“嗯，能招到就不错了，挺难招的，所以……”

Lenny Rachitsky有意思。我记得 Jason 的建议好像是立刻招两个人。

Jen Abel没错。

Lenny Rachitsky这样你就能比较他们。你同意吗？

Jen Abel百分之百同意。因为失败率有 50%，我觉得这个判断完全对。所以对，即使这要求很高，也去找两个好的人吧。但我觉得那样是对的，因为一半都会失败。

Lenny Rachitsky好，我再问你一个读者问题，来自 Hang Huang。这次方向有点不同。他说：“最大的挑战永远是怎么穿透噪音，拿到和正确决策者的第一次会面。你到底怎么让他们注意到你？”

Jen Abel还是要靠 vision。你到底在卖什么机会？如果他们对这个机会感兴趣，就会愿意接电话。我经常这么干，而且别把整块蛋糕都送出去。控制在三句话以内。我知道我上次也说过，但你得说点反直觉的东西，让对方觉得不一样。让他们觉得，接你这个 15 分钟电话能学到东西。你会看到那种常规话术，比如“我看到你的 LinkedIn 了”、“你想把业务增长 15% 吗？”这是什么鬼话？

Lenny Rachitsky这就是他们收到的 cold email 里的话术。

Jen Abel对。

Lenny Rachitsky很棒。那这正好引出另一位读者 Hugo Alves 的问题，他是 Synthetic users 的联合创始人。他问：“从健康的 inbound 转到 targeted outbound，最好的建议是什么？”

Jen Abel健康的 inbound 通常是 marketing-led 的，所以那本来就是 marketing 的游戏。要看你卖的 deal value 是多少。你是卖 5000 美元的单子吗？那就得是 marketing-led，整个引擎才能转起来。如果你卖的是 10 万美元的单子，那你从第一天就得做 outbound。所以这里还是要把问题拆开看。我看到的是，这个问题混在了一起。到底你是在做 small business 那种 marketing-led 的活动，还是在做一个 sales-led、卖 10 万美元单子的组织？

Lenny Rachitsky而这点重要的原因，万一不明显的话，就是如果你卖的是 1 万、2 万美元的单子，你是赚不到钱的。大家花时间去关单，那些单子只带来 1 万、2 万美元的收入，ROI 根本不成立，不适合你的商业模式。

Jen Abel对，没错。

Lenny Rachitsky顺便说一句，Jen，这场对话已经非常精彩了。我们已经聊了……

Jen Abel哦，这太棒了。

Lenny Rachitsky……这么多内容。完全就是我希望聊到的那些点，而且我们已经讲了很多我觉得会对很多人特别有帮助的建议。还有几件事，是你的搭档 Justin 也建议我问你的，我想继续碰一下。其一是，你经常会问 founder 一个问题，这个问题会一下打开他们的思路。你会问：“如果你把产品免费送出去，真的会有人用吗？”每个 founder 都会说：“当然会。”然后你再问：“那客户会用吗？”他们就会说：“呃，那不会。”这个问题一下就把他们打懵了。你聊聊这个问题的力量，以及你建议别人怎么去用它。

Jen Abel我一直都说，要去问那些你害怕问的问题，因为真相会一步一步把你带得更接近答案。所以我会在电话里直接问客户：“老实说，我们觉得今年能把这单做成吗？有这个可能吗？”他们会给你真实答案，而人们其实是怕问的。但另一面是，如果他们真的跟你站在一边，他们就不会在意这个问题，对吧？

这种问题不能在第一天就问，不过如果已经到了那个阶段，而且我们前面没聊到，但这点可能很重要。我做过的每一单 enterprise deal，最后基本都是靠短信敲定的，不是靠 email 了。你是在和一个人建立关系；如果我的 enterprise 客户给我打电话，我会立刻接，或者立刻回，因为这会建立非常多的信任。
如果他们知道可以找你，而且你一定会接，他们就会知道你会尽一切可能把这件事做成。别人会愿意替你翻石头、找办法。我有一个 Fortune 10 的客户，我当时跟她说，今年把这单做成真的特别重要，这有可能吗？她说，难度很大，但如果这能帮到你，我们就想办法做。
这就是 enterprise deal 的做法，靠的是关系，靠的就是这些。所以我才一直说，deal 的 structuring 要做得像你真的替他们上阵过一样，而且很多时候你确实就是在替他们上阵。要按对他们有意义的方式去设计。大家总想把事情塞进固定模板里。对 1 万美元以下、1 万美元级别的单子，pigeonhole 式的 deal structuring 很重要。但 10 万美元的单子，每次通常都会长得不一样。

Lenny RachitskyApril Dunford 上过这个播客，她分享过一个很有意思的洞察：人们之所以会这样，是因为公司里负责买这东西的人，自己的屁股也在火上。他们的名声也压在上面，所以他们希望事情真的成。

Jen Abel没错。毕竟这种事不是每年都做。他们可能每三年做一次，每两年做一次，或者每五年做一次，天知道。反正不是每年都做，很少见。没人喜欢新工具，没人。你、我都不喜欢，除非它真的改变一切。

Lenny Rachitsky对，Figma 就是个很好的例子，Slack 也是。

Jen Abel你接触到的一切……

Lenny Rachitsky那些最后都成了的东西。你说过你会问一些别人害怕问的问题。还有哪些你经常会问、但别人不敢问的问题？

Jen Abel我会直接说：“听着，这是一个 15 万美元的合作。我可以跟你一起把它共同写出来，如果你还需要别的，我们可以把它再做大一点；如果第一年想小一点，也可以先小一点，但到第二年它会往上走。我们怎么把这事做成，让你去争取的时候是个 win？” 如果对方会不会反过来开始砍价？说实话，我从没见过，因为到了那个阶段你已经有关系了。

所以共同把价格写出来这件事特别重要，因为他们得知道，等他们去争取时，可以说：“我从他们那儿拿到了这个。如果把这单做成。” 这也是我为什么说每一单看起来都不一样——你问的是很好的问题，因为这也解释了我刚才那句话的意思。但这也是为什么 enterprise 里的每一单都会显得有点不同，因为很多东西都是共同写出来的。所以如果有人想要稍微低一点的价格，那就给他，但也许可以让他签得更久一点。

Lenny RachitskyJustin 还有一个点，你之前也提过一点，就是当你说 no 的时候。Justin 的说法是，Jen 总是说 no 是 yes 的最好答案，因为 no 本身就是可以用的数据。讲讲这个。

Jen Abel我在资格判断这件事上特别较真。我不会再跟一个人约第二次会，因为第一次通话里要么是 yes，要么是 no，没有中间态。人类嘛，我们既很不同、很不可预测，但同时又很可预测，对吧？如果一个人是真的兴奋、真的想做，和他只是出于礼貌，区别会非常明显。

所以我会在电话里直接说：“我有种感觉，这可能不是一个合适的 fit，或者时机不太对。是我理解错了吗？” 他们通常会说：“对，你说得对，可能确实不太合适。” 然后我马上就会说：“太好了，我很愿意保持联系。你刚刚帮我们保住了一段关系，也帮你自己省了很多时间。”

Lenny Rachitsky这里的意思，还是你刚才说的那点，你的时间很有限。你不想把时间花在那些不会有结果的事情上。

Jen Abel对，没错。

Lenny Rachitsky我再岔开一下，聊聊工具。现在 go-to-market 的 outbound tooling，到底发展到什么程度了？

Jen Abel我不用工具，因为我更信手工，原因我来解释一下。每一条我发出去的 note 都会稍微不一样，因为我会看他们的照片，然后心里想：“哦，这样发出去可能不太能打中。” 或者我会想：“哦，他们可能会喜欢这个，这很怪，但也许正好。” 视觉线索特别有用。照片就是一种视觉线索，再看看他在这个岗位上待了多久、在这家公司待了多久。

Lenny Rachitsky我很喜欢你这么享受这件事。说白了，你到底在干嘛？你是在 LinkedIn 上找人，然后一个一个手动给他们发冷邮件吗？

Jen Abel这事挺奇怪的，Lenny，我完全没有什么流程。我基本上就是跟着感觉走。我会读一篇关于 Tesla 的文章，然后心想：“嗯，他们可能会对这个感兴趣。”不是因为那篇文章跟我解决的问题有什么关系，而是因为我会觉得：“今天挺像个适合联系 Tesla 的日子。” 这很难解释。对我来说，这很情绪化。当然我不是在自夸，但我确实在 sales 上很成功，而最成功的 sales people 也没法解释自己为什么擅长。

它就是自然而然发生的，像一种情绪感受。就像世界上最好的 founder 一样。怎么才能成为一个好 founder？很难定义。怎么才能成为一个好工程师？也很难定义。所以我不信 playbook。我相信的是手感。我曾经给一位 hedge fund 的 chief legal officer 发过邮件，因为我故意选在周六发，我知道他会很忙。我只写了一句话，而且是专门给他改过的。

Lenny Rachitsky你觉得在 AI SDR 逐渐接管、大家每天都收到一堆 AI 味儿很重的邮件时，事情会变成什么样？

Jen Abel会。

Lenny Rachitsky那我想再听你多讲一点。是不是说真正的 alpha 就是做人味儿？别自动化？你觉得应该怎么想？

Jen AbelAI 工具的问题在于，它们抓的都是同一批数据库。所以我会想：“我想发给那些不在数据库里、但正被一百万个人轰炸的人。我想走后门，不想走大家都挤在一起的正门。”

Lenny Rachitsky而且这套方法对特别大的 deal 也有效，而这正是你本来就该做的，因为这种做法很花时间。

Jen Abel对。

Lenny Rachitsky有意思。所以你不是坐在 Clay 里，也不是 Apollo 那一套，我没有这些工具。你是自己找人。

Jen Abel对。

Lenny Rachitsky那你至少会先有一个目标名单吧？比如“这些公司最合适，我们就一个个去跑”。

Jen Abel全在我脑子里。我做这个太久了，脑子里已经有一套。比如这些就是我的 early adopters。这些是我拿下那些 logo 之后，会去找的对象，因为他们会被那些 logo 激发兴趣。说到底就是经验：你拿下 Walmart 之后，就去跟整个行业说，“我们在和 Walmart 合作。” 但如果你去找一个下游一点的 enterprise 公司，他们会说，“等等，你到底是干嘛的？” 他们根本想象不出来。

而且最有战略眼光的人，很多就在这些 Tier 1 logo 里。它们之所以是 Tier 1，就是因为有一群超级聪明、很能干的人。他们还会吸引最好的 talent，而最好的 talent 就喜欢试验、继续改进。所以这就形成了一个复利效应。

Lenny Rachitsky对于不是 Jen、也没有这些经验的人，假设他是 founder，刚到 100 万 ARR，他们可能会说：“好吧，我们去哪儿找客户？” 你有没有建议，怎么想出应该追谁？他们应该用这些工具吗？还是该像你这样招一个人？我知道这就是你帮公司的方式。所以一派是去找 JJELLYFISH 帮忙。

Jen AbelFounder，我会说还是 founder。这个东西其实跟他们是同频的，只是他们要自己找到它。说起来很奇怪，我也不喜欢这么说，因为这话太像陈词滥调了，但确实有一种 flow 的东西。比如有些品牌现在就是跟你在一个 flow 里，对吧？你就是从某个地方得到了这个洞察。那接下来是谁？哪些人是附近下一圈会买单的人？

Lenny Rachitsky所以我理解的是，你就是要留意正在发生什么，哪些公司在……

Jen Abel对。

Lenny Rachitsky新闻里、市场上哪些公司在做有意思的事，谁是市场里的 early adopters。

Jen Abel如果这事只是个数据库名单，只是找到对的文案然后群发邮件，那我们现在早该知道怎么做了。

Lenny Rachitsky这太有意思了。好，最后再问一个问题，这还是 Justin 提的。他说你遇到阻力时从不争辩，你会重构对话。如果对方说：“我们已经有 X 方案了。” 你会点头、换个角度，认同 X 方案确实适合那件事，但接着说我们还能做什么。

Jen Abel这就是为什么要卖给 alpha。听着，你刚刚描述的那个问题，你说得对。你确实有个工具能解决它。我们是把你带到更上游的价值那里去。这才是我希望你们能接触到的机会。

Lenny Rachitsky我太喜欢了，Jen。我把我本来想聊的都聊完了。另一方面，我觉得我们还能再聊一个小时，我感觉我们真的应该再来一次。

Jen Abel我们都三回了。

Lenny Rachitsky对，我们得等到下一阶段再来一轮，把大家想继续深挖的那些东西都聊掉。进入我们很激动人心的 lightning round 之前，你还有什么想补充或者分享的吗？

Jen Abel这事真的很难。销售也是一个快速从拒绝里学习的过程。拒绝其实是好事，因为它会逼你学习，而且你再也不想经历一遍，但你得……我不太喜欢用 cringe 这个词。你不能害怕尴尬。把 AI 录音笔带进电话里是挺尴尬的，但给 15 个你真的能提供巨大价值的人发 note，就别怕，也别怕问难问题。要不一样。

整个游戏的关键就在于：“哦，这感觉不一样。” 人们想接触的就是这种东西。可大家又都把自己商品化，模仿别人，模仿所谓 forward deployed engineer。直接改个名字就行了，没必要非用同一套命名。大家都会因为“新东西”而兴奋，因为新东西可能就是下一件改变一切的事。所以我总是说，别只是更好，要不一样。

Lenny Rachitsky这真是个绝佳的收尾。那接下来，Jen，我们进入非常激动人心的 lightning round。我有五个问题，你准备好了吗？

Jen Abel好。

Lenny Rachitsky第一个问题，你最常推荐给别人的两三本书是什么？

Jen Abel我推荐的是 Twitter 账号。

Lenny Rachitsky哦，推荐关注的 Twitter 账号？太好了。

Jen Abel对。

Lenny Rachitsky好。

Jen AbelLenny，等我哪天有时间读书了。

Lenny Rachitsky就是。

Jen Abel就是。其实我很想读书。

Lenny Rachitsky好，那就说说值得关注的 Twitter 账号。

Jen Abel当然。显然有你，你产出的内容真的特别好，老实说。

Lenny Rachitsky谢谢。

Jen Abel你会钻进那些人的脑子里，甚至把他们在 Twitter 上都不会给出的洞察挖出来。还有谁我特别喜欢？Jason Lemkin。做 sales 的话，Jason Lemkin 真的非常值得关注，而且他之前跟你那期也很棒。一定要把那期链接出来，那段内容太好了。我其实从 Matt 那里也学到很多。我很喜欢 Gavin Baker，观点特别细腻。他会把很多显而易见的表述拆开来，给出不少不那么显眼的洞察，他很棒。Jason Cohen，你请过 Jason Cohen 上节目吗？

Lenny RachitskyJason Cohen，Smart Bear 的 Jason Cohen？

Jen Abel对，对，对。

Lenny Rachitsky他年底或者什么时候会来播客。

Jen Abel哦，太好了。这波安利太到位了。

Lenny Rachitsky是的。

Jen Abel对，这三个会很不错。我知道他们都是男的，不过。

Lenny Rachitsky很好的建议。

Jen Abel对。

Lenny Rachitsky下一个问题，你最近有没有特别喜欢的电影或电视剧？我知道你说过你有时间看书。

Jen Abel说出来有点丢人，Baywatch。

Lenny RachitskyBaywatch。

Jen Abel对，Baywatch 频道。它特别“numby”，而且就是那种 90 年代经典，Baywatch。

Lenny Rachitsky哇，这个我还真没听过。你说的是原版 Baywatch，和谁一起？

Jen Abel原版 Hasselhoff，David Hasselhoff。

Lenny Rachitsky对，还有 Pamela Anderson。

Jen AbelYasmine Bleeth，Pamela Anderson，原班人马。

Lenny Rachitsky太棒了。

Jen Abel对。

Lenny Rachitsky好，来个冷门题。你最近有没有发现什么特别喜欢的产品？

Jen Abel我现在最喜欢的就是一个叫 Playground 的 app。它会把我家小孩在幼儿园里的照片上传上去，这样我就能每天看到他在幼儿园里都干了什么。

Lenny Rachitsky太棒了，我也需要这个。我们现在是邮件加 Google Photos，我真的很想要这种东西。

Jen Abel对，还有一个叫 ClassDojo 的。类似的有好几个，不过这家 preschool 用的是 Playground。

Lenny Rachitsky我很喜欢 ClassDojo。我是个小股东。

Jen Abel真的吗？

Lenny Rachitsky对。

Jen Abel哦，那太好了。

Lenny Rachitsky你看。还剩两个问题。你有没有什么最喜欢的人生格言，会在工作或生活里反复想起、觉得很有用？

Jen Abel有，直接一点。去掉废话。给我 bullet，不要 paragraph。

Lenny Rachitsky最后一个问题。我听 Justin 说，你从来没读过销售书，你就是自己学会的。假如你要去读一本销售书，或者你想向某个你仰慕、学习的人取经，在 sales 这个世界里，还有谁是你最尊重的？

Jen Abel我觉得 Jason Lemkin 对 sales 的理解最强。他的内容太厉害了。我的意思是，他讲这个东西讲得很清楚、很干净。还有我前面说过的，他是个超级值得关注的 Twitter 账号。我是他的铁粉。

Lenny Rachitsky太好了。

Jen Abel我其实也从他那里学到很多。那个 50/50 的说法，或者说干脆招两个人，他都说得很准。失败率其实可能比 50% 还高。

我太喜欢这哥们了。而且他现在特别 AI-first，整个人都在 build。他那些吐槽差点把 Replit 给掀了，Replit 因为他又轮了一整波新的……

Jen Abel他应该多互动一下。有时候他说话挺狠，但你又会想：“他说的也没错。”

Lenny Rachitsky太喜欢了。我得再把他请回播客。

Jen Abel对。

Lenny RachitskyJen，这一期太精彩了，完全就是我想要的效果。我感觉听了这一期的所有 founder，在成交能力上都升级了一截。因为你分享的这些建议，我们会创造出大量经济价值，也会让很多 VC 很开心，毕竟会有很多单子因此被签下来。最后两个问题：如果大家想跟你合作，或者在线上关注你，应该去哪里找你？以及听众怎样才能帮到你？

Jen AbelTwitter。每次新的学习或者出糗，我都会发到 Twitter 上，所以基本就像我的私人日记，而且我在 Twitter DM 里回复得很快。

Lenny Rachitsky你的 Twitter handle 是什么？告诉大家一下。

Jen Abel是双 J，也就是 `J-J-E-N_A-B-E-L`。

Lenny Rachitsky你这名字确实不太好找，不过我们……

Jen Abel对，我知道，我知道，我知道确实不太好找。

Lenny Rachitsky那这个 J 是 JJELLYFISH 的那个 J 吗？多出来的那个 J 是怎么来的？

Jen Abel对，就是双 J。然后呢，别人已经注册了那个 handle，所以我就想：“那我得用自己的名字。”

Lenny Rachitsky明白了。顺便说一句，给大家讲讲 JJELLYFISH 是做什么的，可能也挺有帮助。

Jen Abel对，JJELLYFISH 是一家咨询公司，帮助大家做 zero to one 阶段。现在我在 State Affairs 做 enterprise 的总经理，它基本上是在给公民和公司一个窗口，让他们看到州议会大楼里到底正在发生什么。州政策对你的影响其实比联邦政策大得多。联邦政策更多是写给……

Lenny Rachitsky太厉害了。我最近才知道你现在在做这个，真的超级有影响力，也特别重要，所以谢谢你在做这件事。

Jen Abel甚至是民主本身。

Lenny Rachitsky没那么夸张。Jen，非常感谢你来。

Jen Abel非常感谢你，Lenny。这次太好玩了。

Lenny Rachitsky大家再见。非常感谢收听。如果你觉得有价值，可以在 Apple Podcast、Spotify 或你最喜欢的播客 App 上订阅这个节目。也请考虑给我们打个分或者留个评论，这会很有帮助，让更多听众找到这个播客。你也可以在 lennyspodcast.com 找到所有往期节目，或者了解更多这个节目。我们下期见。