What world-class GTM looks like in 2026 | Jeanne DeWitt Grosser (Vercel, Stripe,

Lenny RachitskyI've been getting so many asks for go-to-market help.

Jeanne DeWitt GrosserWith AI, it's just intensified because you have 10 players pursuing the same market opportunity and so your ability to actually bring the product to market to differentiate yourself from the competition has become more strategically important than it was previously.

Lenny RachitskyI had Jenna Abel on the podcast recently, one of her tips is you don't want to be focusing on here's the pain and problem we're solving and instead focus on here's how you will be better than your competitors.

Jeanne DeWitt Grosser80% of customers buy to avoid pain or reduce risk as opposed to increased upside, which is a good thing for startup founders to understand. We all love to talk about the art of the possible, everything we're going to enable in the future, but that's often really a sale that's going to resonate with another founder. For everybody else, particularly enterprises. You're avoiding the risk of not making your revenue target next quarter.

Lenny RachitskyI've heard a lot about how you think about go-to-market as a product.

Jeanne DeWitt GrosserWe buy a lot of things because of how we feel about them. The experience that you have of being sold to will increasingly actually differentiate a company and drive buying decisions if products are only different at the merchant. And so then you really want to create a customer buying journey that feels like very unique experiences.

Lenny RachitskySomething I've heard from so many people you've worked with is that your superpower is building a sales org that doesn't feel like a sales org to engineers.

Jeanne DeWitt GrosserThe litmus test I have always given my sales team is if you are an account executive in my org and I put you in front of 10 engineers at our company, it should take them 10 minutes to figure out you aren't a product manager.

Lenny RachitskyToday my guest is Jeanne Grosser. Jeanne was chief product officer at Stripe where she built their very early sales team from the ground up. She's currently COO at Versel where she oversees marketing, sales, customer success, revenue ops and field engineering. Jeanne has built world-class go-to-market teams at multiple unicorns and has advised dozens of companies on doing the same. In our conversation, we go deep on what a world-class go-to-market team looks like, including what the heck is go-to-market, the rise of the go-to-market engineer and how this role is already enabling her team to operate 10 times faster. A bunch of very specific tactics to level up your go-to-market skills, a primer on segmentation, how to think about your go-to-market process like a product, her favorite go-to-market tools, her hot takes on PLG and sales comp and sales hiring, and so much more. If you are looking to get smart on the latest and greatest in go-to-market thinking, this episode is for you.

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Jean, thank you so much for being here and welcome to the podcast.

Jeanne DeWitt GrosserThanks for having me. Lenny.

Lenny RachitskyWhat I wanted to get out of this conversation by the end of this to basically have this conversation be the thing that we send people when they're like, "I want to get better go to market. I'm trying to figure out what to do and get to market." We send them this versus having to hire someone for a lot of money and usually they can't find amazing people, because they're all snatched up. So let me start with just the basics. When people hear at the term go to market, what does that mean? What does that encompass?

Jeanne DeWitt GrosserI think there are two answers to this. Often what people think of is sort of the tip of the spear of what drives revenue, which is marketing and sales. For me, I think of it as any function that is going to touch a customer or make a dollar, and actually my remit at Vercel is that, so that includes marketing, sales, all of your technical sales roles like sales engineers or post-sales platform architects is what we call them at Vercel. It's customer success, it's support, it's partnerships. And the reason I say that is my experience throughout my career has been that those functions often have this Venn diagram strategy where marketing's pursuing one thing, it overlaps with what sales is pursuing, but not perfectly, which also overlaps with what support is pursuing but not perfectly. Examples of this would be slightly differing segmentation frameworks, et cetera.

And so one of the things I think you're going to want to see more in this particular moment is that that become a really integrated lifecycle. In particular, I think we're going to see a lot of the functions of go-to-market get redefined, so we've gone through a period of hyper-specialization in go-to-market depending on how you count them. There are, I think somebody quoted 17 different roles within go-to-market these days and I hypothesize that a lot of those are going to start to collapse. And so if you think of go-to-market more holistically, I think you can kind of go back to what are the jobs to be done from making a customer prospect aware of your product all the way through to high LTV, five years on the platform, fully wall-to-wall, and you're going to want to map that out and orchestrate it the way you would think about that within your own product.

Lenny RachitskyAwesome. We're going to go through that whole cycle of go-to-market, but so is it safe to say just for most companies that are especially starting out when they say go-to-market, that mostly is sales and then there's marketing as maybe a smaller fraction of that and then as you become more advanced and grow, customer success plays into it, tech sales, things like that?

Jeanne DeWitt GrosserYeah, that's probably where most start is getting sales or frankly just because a lot of companies also start PLG, you might actually start with marketing and then you're layering in sales when it's time to do the sales assistant and ultimately sales led portions. So I think it can, depending on your product and your initial target market, it can either mean marketing or sales or a combination of those two.

Lenny RachitskyAwesome. So essentially it's like the term go-to-market tells you what we're talking about. How do you take your product to market, get people aware of it, using it, sticking with it?

Jeanne DeWitt GrosserYep, absolutely.

Lenny RachitskyWhat has most changed in the world of go-to-market over the last few years? You've done this for a long time at Google, at Stripe, you built it for sales team, now you're doing that at Vercel. What's changed most in the skill and art of go-to-market?

Jeanne DeWitt GrosserThere are a number of things. So when consumption-based business models started, I think you saw go-to-market shift into being meaningfully more consultative because often that first land was the very beginning of the journey and represented a very small percent of what you were ultimately going to do with that customer. And so you had to go from being transactional to a lot more. You had to more deeply understand what that customer was trying to do so you could align that ultimately to your product. I think that has played out that much more with an AI because right now everyone knows they need to change, but they don't necessarily know exactly what they need to change to, whether that's their customer-facing product or their internal productivity and workflows. And so I think you're seeing a lot more of go-to-market orgs leaning into the art of the possible best practices, helping you actually think things through as if they were a consultant.

And so one of the things you see more of right now is forward-deployed engineering, which on some level is kind of a rebrand of professional services but kind of not. And a big part of that is, hey, how do I actually get into your environment, ride alongside you better understand what you're trying to do and then help you actually bring the technology to life and learn a lot along the way.
Often you're not only making that customer successful, but you're then taking all of that back to your product and engineering organization to figure out, okay, what was generalizable that we ought to build into our offering versus what is something that ultimately is going to be more of a professional service in the fullness of time. So I think that has been a biggie, is actually just really getting embedded with your customer. And then unsurprisingly, I think bringing AI to bear on the sales process is another big one. And so you've seen the rise in probably the last 18 to 24 months of the go-to-market engineer, which different folks define slightly differently, but it's kind of bringing one technical prowess to bear on go-to-market in general so you can have a lot better tooling, data use, et cetera. And then two, increasingly bringing AI to bear as well to re-architect your workflows and also make it so that it's easier to have a personalized experience with customers but do so at scale.

Lenny RachitskyAmazing. Okay, let's follow the thread on this go-to-market engineer, so what was it like before and what are these engineers doing at companies?

Jeanne DeWitt GrosserSo I think maybe an interesting story to tell. When I was at Stripe, we went to launch an outbound SDR function. So outbound prospecting and Stripe always ran lean. The company at that time had an operating principle which was efficiency is leverage. And so if you looked at the sales organization I was running, most companies out there probably would've had 30 SDRs and I was going to get four. So there's no way I was going to do the typical SDR approach and be successful. And so we thought to ourselves, okay, what can we do? We'll be super data-driven. And so we went and we started building project Rosland. Rosland is the scientist who originally mapped A-DNA. And what this was was effectively a company universe. So you can think of this as a massive database. Every row was a different company on the planet and every column was an attribute about that company that would help you sell to them in a more targeted fashion.

So at Stripe an example would be knowing that their business model was a marketplace was super helpful, because that would mean you wanted to sell Stripe Connect versus vanilla payments. And so the goal was basically, hey, can we create a mad Libs where I will come up with sort of a predefined email template, but 80% of it will be fill in the blank based on the different attributes of that customer. So if they're this industry or this business model, then pull this customer, reference this value prop, send it to this persona, not that. And we were trying to do this in 2017 and it was very hard and didn't actually totally work our ability to the false positive rate and we worked deeply with DSI and it just never really got there. And now that we're literally redoing here at Vercel as we speak and it actually works and you can bring AI to bear on it.
And so what's different is we now, I have a data scientist just like I did back in 2017, but I have a go-to-market engineer whereas before I just had someone in systems that was helping me configure outreach or sales off and my go-to-market engineer is helping me build an agent where we're coming up with, okay, well what's the human workflow that you would've done? And then how do you encode that using Vercel workflows as an example in actual code that's both deterministic and less so where an agent's going out and trying to replicate what a human might've done to produce that, fill in the blank, matlit.

Lenny RachitskyI love the ambition of that project. What is this, like eight years ago?

Jeanne DeWitt GrosserYes.

Lenny RachitskyI love the big thinking there. We're going to map the entire universe of companies and then here's how we sell to them. And then just I'm trying to picture doing that without AI. It's like crazy to imagine trying that without AI and that's so much simpler to even imagine.

Jeanne DeWitt GrosserWell the thing that's amazing about that, just to geek out on a second, so I was working on that with a bunch of folks at Stripe on my team, obviously at a gentleman named Ben Salzman who went on to go to ZoomInfo and then actually recently just founded a go-to-market startup that is basically sort of productizing that concept of a company universe and then layering AI on it on top of it. And ultimately his view is actually AI will get to the point that you won't have to do outbound prospecting because it will just sort of company and product match. So it's fun to sort of see back in 2017 some of the folks doing that now work at OpenAI, they work at Anthropic, they also are doing GTM Eng. You've got him starting a totally AI native GTM company and then here I'm at Vercel trying to do the same.

Lenny RachitskyOkay, so what's cool is this is an emerging role, an emerging skill that I don't think a lot of people have recognized as something that is happening. So one example I'm hearing of what this role does is they automate outbound emails essentially and outbound outreach. They figure out, they write workflows and agents that figure out here's the company to go after, here's how we message them. Does that end up being kind of like an email that's custom designed and written for this prospect?

Jeanne DeWitt GrosserThat's one version. So it's broader than that really. Basically the full remit of GTM Eng will be to go through each of the different functions within go to market and break down all the different workflows that they do and then turn those into agents where AI is better placed than the human to do that task. So right now we started with actually inbound and are now moving to outbound because that workflow is most legible. And by legible I mean you can basically write it down. It's relatively replicable, mostly deterministic. So it's more likely that AI will do it well and we actually built the agent and then we keep a human in the loop. But from there we're starting to look at outbound and with an outbound we're starting more at the lower end of the market, where you tend to have slightly less customization because there's a single decision maker at the company.

But I think it'll take a while before we're able to really do that in a very large enterprise. There we might use an agent for research but maybe not all the way to actually send a message and that's just within the prospecting function. So other places that we're looking at this would be for install-based sales. So again there it's a little bit more deterministic because you've got awesome internal data on what a customer is and isn't using, what's the next best action? What's the thing they should get most value from? So that's where we're starting to map, hey, what does that ideal workflow look like? But basically you want to get to a state where as long as I've been in sales, they release these annual reports that help us all benchmark ourselves relative to one another. And one of the stats is what percent of time do your sellers actually spend in front of customers?
And for the 20 years I've been in sales, it's always been somewhere around 30% to 40%. So the minority of time is actually talking to other humans and I think we're getting to a point where with layering in agents, ideally we finally get salespeople to a point where they're actually spending 70% of their time interacting with humans and we can get the research, the follow-up, the things that are a little bit more rote and don't use the entirety of your human capacity done by an agent and then sort of unleash you to go deeper with your customers.

Lenny RachitskyI love that this is such a great example of where AI is contributing in a very meaningful high ROI way, taking on all this work that people... like, you have to hire say 50 SDRs as you described to do and now you could do with a lot more. So it's a really cool example of leverage that AI gives you. One thing that I know a lot of people think about when they hear this is, okay, I'm going to get more of these really bad emails trying to pitch me on stuff and just like this isn't going to work. I can tell this is AI. What have you learned about how to do this where people actually receive emails that actually convert and do well?

Jeanne DeWitt GrosserOur processes all always have human in the loop. And so basically where we'll start is we take a go to market engineer and we have them shadow the highest performing individual in that function. And so you can go and you shadow an SDR and you can see, oh wow, they've got seven tabs open. They're looking up the person on LinkedIn, they're reading about the company, they're doing chatGPT on this, they're looking in this database to get these sets of attributes. And so that's how you sort of inform the initial workflow. And then what we do is we let the agent make a call. So in the specific example with inbound, you have to determine whether or not you think the lead is likely to be qualified and then you have to determine what to say to it. And so we'll let the agent make those two calls.

It ultimately then does some deep research, pulls in a bunch of information from our databases and crafts a response, but we have a human review all of those and actually hit send. Now for us, we had 10 SDRs doing this inbound workflow and now we just have one that is effectively QA-ing the agent. The other nine we deployed on outbound, so we got to move them up the value chain. At some point I think we'll get to a place where we feel like, "Hey, the human reviewer is saying yes enough of the time that we feel confident that these will be on brand targeted, et cetera," but right now we're still trying to train the agent and it incorporates feedback on what we choose to reject, edit, et cetera.

Lenny RachitskyAnd you shared that it's already having a lot of impact. Like you said, you had 10 SDRs and now one can do the job of 10.

Jeanne DeWitt GrosserSo before we did that move, I mean the other thing that's just incredible about this is the person who built the lead agent was a single GTM engineer. He spent maybe 25-30% of his time on this. It was six weeks before we felt confident going from 10 to one. So it wasn't like this was a multi-quarter process, it actually moved super quickly and then again now we just sort of keep that agent manager working with the agent to get it to a point where we say, "Hey, we're ready to roll." Actually throughout the process we also tracked all of the KPIs that you typically would hold an SDR accountable to. We were looking at our lead to opportunity conversion rate, we're looking at the number of touches it takes the time to convert, and basically what we were able to do is hold that lead to opportunity conversion rate flat. So the agent is as good as our humans were, but it's actually condensed the number of touches it takes to convert because it's so much quicker at responding relative to leads inevitably sitting in the queue or coming in at nighttime and no one can get to it, that type of deal. So that's sort of when we knew it was ready to pull nine people off and shift them into outbound.

Lenny RachitskyThat's incredible. Okay, that's interesting. So you shift them to outbound. What I love about this is this SDR that is now doing this is, as you said, doing the things they enjoy more, they're talking to customers more, they're not doing all this kind of top of funnel rote work. I don't want to get into whole jobs AI discussion, but there's always been this talk about AI SDRs basically replacing SDRs. It feels like that's one thing where everyone's like this is a hundred percent going to be AI in the future. What I'm hearing here is it gives one Aster a lot more leverage and obviously you still need people running the show. Thoughts there? Just like do you think AI will replace all this at some point? And then I don't know, you don't need salespeople?

Jeanne DeWitt GrosserI think on prospecting it can replace a fair amount because the average SDR wasn't doing overly sophisticated research in the first place. So where I, think the last part to go as I mentioned will be in deep enterprise prospecting where you can be at multiple layers in an org chart, you've got to pick between business lines, you've got to triangulate those. But I do think for the things that are more repetitive that often don't take that much time to learn and get ramped, AI will be good at that. And in my view, no one graduated from college and was like, "Yes, I just went to college for four years to become an SDR." It was more, "Okay, that's where you are forced to start." But I think the average SDR could have gone straight into outbound or straight into an SMB closing role. And so basically what we're just doing is shifting folks into something that uses more of their full capacity right out of the gates rather than sort of the forcing function of working your way up the totem pole.

Lenny RachitskyAwesome. Since a lot of people listening to this aren't salespeople don't have a lot of background in sales, we've used this term SDR, there's also the term AE. Can you just help people understand what is an SDR, what do they do, what's an AE, and then what's the role above?

Jeanne DeWitt GrosserSure. So SDR is typically in charge of generating pipeline. They're meant to talk to prospective customers and get them to a point where it is worth investing time to run them through a sales process. You typically have two types of an SDR, have an inbound one. So this is where people come to your website, they fill out contact sales, they'll be the first call to make sure that it's actually worth a more expensive account executive to go and run a sales process or you then have outbound. So this is where when you want to grow faster than your inbound demand, they will go out and at this point you probably have a point of view on where you think you have product market fit. And so they will target that part of the market and try to drum up interest from folks who weren't otherwise raising their hand saying, I'd like to talk to you.

So that's sales development basically. Pipeline generation account executives are closers. So it's their job to take somebody from, "Okay, hey, I'm interested in learning about your solution, I have a legitimate problem. I potentially could make a decision," to, "I now believe that your product is the best in the market for me and I'm willing to pay for it." And then account executives, depending on the segments that your company sells into E.G. small business, mid-market enterprise, et cetera, they may work their way up the food chain from selling to a smaller company like an SMB or a startup. Those tend to be a little bit more of a transactional sale. You often have a single decision maker to then going into a mid-market or a commercial role where now maybe you have an economic buyer like somebody in finance and a technical buyer like somebody in engineering to getting into enterprise where you have procurement and you have committees and 10 people have to weigh in and you've got to help them figure out how to de-risk the fact that they're probably migrating from something so much more complicated coordination effort to sell.

Lenny RachitskyThat was extremely helpful. So SDR, pipeline generation, i.e., closer. Such a simple way of thinking about it. Okay, this is great. Going back to the GDM engineer, a few questions for people that may want to try this at their company, what scale do you think it makes sense to start hiring for this role? Having someone automate in the go-to-market process?

Jeanne DeWitt GrosserWhat's interesting about this is it will force companies to be more rigorous about their sales process early. So often startups when they go from founder led sales to say, I'm going to have my first sales person, whether that's an actual account executive who has sales experience or your general athlete, wicked smart, who's going to go figure it out. Often founders will just say, "Okay, sales is showing up and talking to people. Isn't that what I just did for the last couple of years?" But actually sales is more than that. It's a skill just like writing code as a skill or building a financial model as a skill, it's about discovery. So asking all the right questions that help you identify challenges in pain, willingness to pay, et cetera, and then going through a process to handle those objections and showcase where are you at enough value such that somebody ultimately wants to hand over some money.

So often startups will get, particularly ones with strong product market fit to pretty significant scale without really having a replicable process. And you can't really apply go to market engineering unless you actually have a point of view on what best practice should look like. And so I think basically this is going to force folks to have more of a playbook out of the gates, what's working, what's not? Can I document it? Do I have content for the different parts of the sales process? And then once you do that, which maybe 10 people is a good size and scale for that, ostensibly a GTM engineer can come in and turn that into an agent. You could also argue that if you're a founder who wants to bring in a general athlete profile and that person is technically minded, that you could have a hybrid AE GTM engineer who figures out what their best practice is and then tries to turn that into an agent that's riding alongside them and making them more effective as well.
So I don't know that I have a point of view yet on what's the optimal size and scale, but I forever have given founders the advice that you often want to bring in revenue operations, which is basically the analytical arm of sales earlier than you think because having data, having process is actually what gives you insights as a founder into what is and isn't working. And so I would argue just like it's a good idea to have that sooner than later, increasingly it'll probably be a good idea to have GTM engine and be looking to bring agents to bear on your process at the outset.

Lenny RachitskyWhile we're on this topic, just a quick tangent, the advice for hiring your first salesperson that I usually hear is wait until you're around a million in ARR. When you have a repeatable process, you can teach someone anything there. Does that seem right? What would you recommend?

Jeanne DeWitt GrosserYeah, I think that seems about right. I do think as a founder you want to stay deeply connected to customers and get it to a scale and get it to a point where you use the word, there's some repeatability there. I think that's one of the things that not all founders get right is founders are incredible salespeople. They convinced a VC angel investors to fork over a bunch of money, so clearly they're going to inspire people to buy. But if you're getting to a million in ARR and the set of customers you have look nothing like one another, you still have very much like an evangelist sale, very much founder led sale versus if you can say, "Hey, I now have an ICP here, or ideal customer profile, e.g something you can write down. We are good. Our product fits with startups with less than a hundred employees who are typically building SaaS applications," something like that.

Then you're probably ready to hand over the reins. And then what founders have to remember is to actually hand over the reins. So you've got to enable the person who comes in, what is it that you're doing effectively, what's your content, what are the discovery questions you are asking? How are you handling objections so you can transition that knowledge but also don't handle them over entirely. You want to stay connected to the customer because you still have a fair amount of R&D to do to figure out where is the product next going to resonate, where are you getting stock as you scale, etc.

Lenny RachitskyTo close the loop on the go-to-market engineer, what's the profile of the ideal go-to-market engineer, may be your first.

Jeanne DeWitt GrosserWhat we have found works really well is somebody who does have go-to-market experience. So at Vercel, our first three go-to-market engineers we're actually sales engineers. So Vercel hires very technical sales engineers, all of them were front end developers before they decided they wanted to get into sales. And so we just said, "Hey, three of you, congrats." You're now founding members of our GTM Eng team. And the thing that works well there is you do understand aspects of what is good GTM, what does a process look like? It's been really interesting actually. So the gentleman who runs GTM Eng for me, we were going through this lead agent and QA-ing it. And so I'm going and I'm looking at some of the responses that we've ultimately had the lead agent send and realized, "Oh, I wouldn't have sent that and that's because I have 20 years of sales experience and we modeled the lead agent off our best person, but our best person who has two years of sales experience." So it actually is important to understand the art and the science of sales and how you bring best practice to bear. Either you've done it and so you know some best practice or you're going to geek out on sales, read a bunch of books, learn a thing or two, and try to incorporate some of those into your agent development.

Lenny RachitskyThat is really interesting. So come from the sales side, not from the engineering side. And I imagine this is such a cool opportunity for salespeople to do something completely different and move closer to engineering.

Jeanne DeWitt GrosserYeah, I mean we're having a lot of fun with it. At Vercel in particular, we basically get to be customer zero. So everything that we're building with agents, we're building on Vercel's AI cloud. So these agents now have multiple steps that they go through. So we're using Vercel's workflow SDK and workflow offering. We use the AI gateway to call the different models that we use to do deep research or other enrichment that we do. So for us it's great because we basically sort of bang on everything the engineering team is building and get to go be a discerning customer before we actually get it out the door to real customers.

Lenny RachitskyWhat a fun time to be alive. I could tell the fun that you guys are having, just from the way you describe it.

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Jeanne DeWitt GrosserWell, so I'm going to have an interesting answer to this, so I'll give you one. And it's not state-of-the-art per se, although I don't mean that disparagingly, it's just that it's been around for a while now and a lot of folks use it, but I think Gong has gotten just meaningfully more interesting in the last year. And then second half of my question I will get into, I think the calculus on build versus buy is changing. So all right, Gong. Gong is incredible because you can run agents against it now. So we take all of our Gong transcripts and we dump them into an agent called the deal-bott, and that deal-bott then can do a bunch of things. So the first thing we had it do was lost opportunity review. So we had just finished Q2, we had a list of our top losses for the quarter sorted by deal size, and we ran it against that and it was incredibly interesting.

So the biggest loss that quarter according to the account executive was lost on price. And when you ran the agent over every Slack interaction, every email, every GONG call, it said actually you lost because you never really got in touch with an economic buyer. And when you talked to somebody about ROI and total cost of ownership, it was clear from their reaction that they didn't really buy your mass. And so really the reason we lost was an inability to demonstrate value, which upon reflection I've got work to do to build out how we quantify the value of Vercel, which actually is very easily quantifiable. It's one of the things I love about selling this product, but we got to codify that for the go-to-market team. So that was incredibly interesting and now we run it against all of our lost opportunities and actually do a much better job of categorizing why it was we really, really lost.
And then either feeding that back into the engineering team or back into marketing sales leadership on, hey, where are we falling short in the sales process? And so that was awesome, but then we're like, well, it's not very fun to lose, so why don't we pull that forward? And so we went from lost bot to deal-bott and now the deal-bott is running in real time and we basically feed insights into Slack. Vercel is incredibly heavy users of Slack, so we have a channel for every single customer, either opportunity or existing one. And so now we're feeding insights into that Slack channel which is, "Hey, you're this far into the sales process and you haven't talked to an economic buyer, you should think about that." Or, "Hey, you just got off that call with an economic buyer, didn't sound like it went that well. Here's some things to consider and how you might follow-up."
And last thing before I pause, the other thing that's really interesting and how we're using this too is we are in this moment where I have never seen an iteration velocity exists now in my career. My 20 plus year career has all been in tech. And so for go-to-market teams, that's really hard. If you are launching something every other day, the ability to be enabled on that is actually quite challenging. And so this bot agent is now also letting us, where we're starting to go with it is we'll release something, we'll do our best to enable the team, then we'll go run the agent across calls, interactions, and we'll diagnose where we did a bad job of objection handling, where we're getting stuck. And then at the end of the week we can have a huddle and say, okay, what are all the places that our agent would suggest we aren't selling effectively?
And then almost like an engineering team, we'll now run sprints, which is like those are just bugs. They're bugs in your go-to-market process, so you should not have them. And by the next week we're going to add content to our objection handling to guide. We're going to add content to a discovery guide, we're going to figure out something we need to change about our demo, so on and so forth. So that's early. That's a little bit of a preview, but that's where we're talking about taking things right now within our go-to-market orgs.

Lenny RachitskyJeanne, you're blowing my mind in so many ways, it just sounds so fun and just you guys are going to win is what I'm feeling when I hear all this. Incredible. What I love about this is this AI tool, this agent you built sees things that humans were not seeing. The fact that you were surprised of just like this is a completely different conclusion is such a big deal. This is the whole promise of ai, it's going to do things we aren't even thinking about or capable of.

Jeanne DeWitt GrosserIt is. We had a really interesting, one of the things we're doing at Vercel, we have an AI cloud, so people use that to put AI-native features into their customer-facing applications, but they're also using it to build internal applications to improve productivity or outcomes. And we are talking to a very large airline and that airline obviously gets tons and tons of support queries. So of course they would want to go apply AI to hey, how can we have AI answer these so that our cost to support goes down, sort of the obvious thing. But the more interesting conversation was actually with one of the C-level executives who said, we also actually transcribe every single one of those support calls. And so what I really want to know is why are they calling and how do I make it so that fewer people call the next week? And so again, this is now with AI, you can rapidly go through all of that content and actually be able to much more quickly than having a human in your CRM sort of pick some status why it was that folks were calling the airline this week and what if anything you can do to make it less the case next week.

Lenny RachitskyI imagine many people hearing this are like, "I need one of these deal-botts and lost bots." These are all internal products that you all built?

Jeanne DeWitt GrosserYes.

Lenny RachitskyIs there anything that you've learned about making them this good? Any tips you can share of here's how to make a really good bot for sales?

Jeanne DeWitt GrosserYes, so actually that's the second half of my answer that I forgot.

Lenny RachitskyThat's perfect.

Jeanne DeWitt GrosserWhich is sort of like bill versus buy calculus. So I think one of our learnings is that it's not that hard to build these agents and they aren't that expensive either. So I mentioned the lead agent that was a six-week process with one human, a third of his time, that deal-bott, the lost bot version was two days basically we riffed on it, he had it 40 hours later. Now we're continuing to refine it for the other things I mentioned. And what's also interesting about them is they for better or for worse for Vercel, but that lead agent which runs full stack on Vercel, will cost us about a thousand dollars to run for the entire year. If you remember I told you we had 10 people in the SDR function, so I'm paying well over a million dollars for that from a salary perspective.

I got that down to one. And then behind that I have a lead agent that costs a thousand bucks. So that's like a 90%-plus reduction in total cost there. And there's lots of software for agents out there right now. And I think one of the things we're learning is because this whole space is so nascent, often your own esoteric context, your content, your workflow is really key to unlocking the power of the agent. And so I think there's real value in experimenting with your own internal agent development. We may ultimately end up on better integrated agent platforms in the fullness of time, or we may find that the CIO increasingly goes from a procurer of software to a builder of software and you'll have an AI internal platform with a thousand agents running across your org. I'm not really sure yet. But I certainly think there's value in trying it yourself because you may find that it's meaningfully easier than you think and you get returns pretty quickly.

Lenny RachitskySo what I'm hearing here is that you're finding that there are not tools out there to plug and play. The alpha is essentially in building your own stuff.

Jeanne DeWitt GrosserI think that's partially true, and I think because you also have all these tools proliferating right now, you get into the perennial problem where you wind up with 20 of them to do the 20 jobs to be done basically, rather than an integrated platform that's doing all of them. I'm hearing this a lot actually when I'm talking to customers right now where their biggest issue in deploying AI is actually just getting through procurement and it's because got an AI mandate, you kind of have a blank check. I recently heard the term of instead of ARR, it's ERR, which is experimental run rate revenue, which is to say everyone's out there sort of, Hey, we're going to give this thing a go for a year and then TBD on whether or not we keep it. But basically you're having to procure 20 different things. Most things are getting off the ground and so they're solving something relatively narrow and that'll change in the fullness of time. But I do think there's an opportunity to figure out, hey, where do I likely have a more specific workflow internally. For that it might be worth building your own agent and then maybe for the things that are a little bit more generalizable, you go get something off the shelf.

Lenny RachitskyAre there any platforms or tools that you want to shout out that allow you to build these agents so quickly? I know they sit on Versel, so shout out Vercel. But just anything that you point people to you to... These SDR, these GTM engineers, they're former salespeople. Are they learning to code? Are they byte coding these agents? How does that work?

Jeanne DeWitt GrosserSo our sales engineers all have CS degrees. So they were engineers in a sales capacity, so they're writing code and actually these agents, they're building directly on Versel. So you get the AI gateway that lets you call different models. You have a sandbox if you're running untrusted code, you've got workflows that let you build the process. You've got fluid compute, which lets you really efficiently use compute when you only need it. So we're just sort of building it from the ground up here. Again, it's not that hard. Now you do need to write code for that. Certainly there are a lot of vibe coding tools out there that also give you more workflow builders that are somewhere between fully WYSIWYG, almost like drag and drop and a little bit more code forward. So you've got a bunch out there along those lines. But I do think we've sort of found one of the reasons actually the GTM Eng team at Versel can build these agents so easily is because the Versel platform is making it that easy to use our framework to find infrastructure and get that agent onto into production very rapidly.

Lenny RachitskyWhat a neat, unfair advantage you all have to do this stuff.

Jeanne DeWitt GrosserYes, it is fun to... I mean, I do think this company is better than any I've seen at eating its own dog food and just everyone is constantly, we say Versel builds Versel with Versel. So you're just always looking for ways to, Hey, how can we use our product to go do what we need to do? And as a result, either understand then what a customer would want or what's missing from our product that we could go make better.

Lenny RachitskyAlong these lines, something that's already come across a lot in the way that you described this stuff is I've heard a lot about how you think about go-to-market as a product. A lot of people listening to this, as I've said, are product builders. So I think this is a really nice way of thinking about go-to-market. I'm guessing you've already talked about elements of this, but just what's a way to think about go-to-market as a product?

Jeanne DeWitt GrosserYeah, I've always, so I had this realization probably a little over a decade ago in my career. So my first job out of college was working on Gmail in 2004. So Gmail launched on April 1st, I joined on June 1st. And as I'm sure you'll remember as well, Gmail was this incredible innovation, massive JavaScript application that didn't really exist at the time. And it had this gig of storage. It was a full year before Yahoo Mail caught up and even longer before Hotmail and others did. So that was the level of technical differentiation between Gmail and the next best. And a decade later, you had cloud computing enabling folks to do stuff that you never would've been able to do previously. And so I kind of felt like, huh, software's starting to commoditize a little bit. And so when that happens, when technical differentiation kind of narrows, what are other things that will differentiate you?

And I was started thinking outside of tech, we buy a lot of things because of how we feel about them. And so I started to develop this thesis that actually the experience that you have of being sold to will increasingly actually differentiate a company and drive buying decisions if products are only different at the margin. And so if you believe that, then you really want to create a customer buying journey that feels like very unique experiences. And so we did a lot of this at Stripe and now we're looking to replicate this here. But an example of one of the things I think we did really nicely at Stripe was a lot of companies sales, the first call after you're qualified, we've decided you're worth engaging in sales process is discovery, which is basically let me ask you a lot of questions to try to under-uncover paint, figure out where buying power lies, et cetera.
And so that is kind of boring sometimes for a customer. You're basically being quizzed often on the phone. And so what we started to do at Stripe was that first session was a whiteboarding session, and we would actually get together and have you draw your architecture for payments and all the other things that were under the hood to enable you to take money and drive customer outcomes. And through that we would learn a ton about what was in your stack, what we were going to have to compete with, displace where value lied. But the customer also learned a lot themselves because in many cases they'd never drawn their architecture diagram. And so they left that meeting with an asset and a sense of like, "Wow, this is a really collaborative person who's deeply interested in helping me develop a mental model for how to think about this." And then we had other things that we would do.
So that's sort of how I think about building go-to-market-like a product is basically you need to go through from the first time you become aware that the company exists to again, that sort of five-year heavily retained wall-to-wall customer a set of experiences. And those experiences can feel transactional, flat, boring, or they can feel very human, personalized and unique. And so we try to go map those out and figure out how do you bring the product to bear, make it really human, and hopefully that creates a customer for life in the end.

Lenny RachitskyI love that whiteboarding example. Are there any other examples of what you've done to make it actually work really well in this way?

Jeanne DeWitt GrosserYeah. Another principle, we really developed this at Stripe too and I brought it to Vercel, was just the idea of adding value at any touch point regardless of whether or not that customer bought. Because even if customers don't buy, you often find that if you miss them on that buying cycle, three or four years later when they're in another buying cycle, they do come back. I was at Stripe for nine years and so I saw the number of customers that we lost and then half a decade later, here they are and they bought. So that was sort of another one. So examples of this that were doing at Vercel is there's great data on the internet that helps people understand the performance of their website and how fast your website is actually impacts SEO. And SEO impacts AEO and everybody's thinking about AEO right now. And, so one of the things we try to do when we reach out is actually give folks insight immediately into how they're performing on an absolute basis, how they're performing relative to peers. So ideally that piques your interest and you want to learn more from us, but even if it doesn't, you still have insights that you may or may not have been aware of that maybe make you contemplate whether or not you've got the optimal setup.

Lenny RachitskyAwesome. So what I'm hearing here is when you say, think of it like a product that's basically a product person thinks about the experience of their product, that every step of the journey, here's the flow, step 1, 2, 3, 4, 5, how do we make every step awesome, keep them going along that journey. And so what you think about is just from the prospect's perspective, how do we make every step of that journey awesome, continue them down that journey.

Jeanne DeWitt GrosserYeah. How do you make it be an experience rather than a transaction

Lenny RachitskyVersus just feel like sales coming at you trying to sell you stuff?

Jeanne DeWitt GrosserYeah.

Lenny RachitskyOkay. Staying along this track of staying tactical, I want to go even further there. So what are just some go-to-market tactics that you find really effective these days for people trying to just to be more successful in getting people to pay attention to their stuff, to buy their stuff?

Jeanne DeWitt GrosserI mean, one I would sort of say dovetails with where I just ended, but is what are the unique insights that you can bring to bear about your product or how that customer may be in a suboptimal state? So I do think investing in data to tease that out is one thing. I think the other thing this is straightforward but often not done enough is a lot of good companies invest in docs, good thing to do, but they stop there. And particularly if you are selling into a slightly larger company doing things like, AWS calls it well-architected guides or blueprints, a lot of customers, particularly larger ones, really want to know the best practice for how exactly to implement your product with their particular setup. A great example of this, this is from Stripe, was Stripe was excellent at marketplaces. Most, Lyft, Instacart, DoorDash, they were all on Stripe.

And so Stripe definitely knew the best way to set up payments for a marketplace because we'd seen them all. And so when you then would go and sell a marketplace and say, "Oh yeah, we've got docs, go check them out." They didn't like that, because they're like, "Hey, every marketplace runs on Stripe. I don't want to look at generic docs. I want you to tell me what's the best way to set up payments for a marketplace." And so I think that's another key thing to be doing, particularly as you move past that sort of solo developer startup founder as potentially a target audience.
And then, I don't know if this is a tactic per se, but I do think just a good reminder for founders in particular who are still in that maybe founder-led sales moment is just the value of really good discovery. I often find founders are so excited about talking about their product or you ask one question and now they've got a hook of like, oh, I can fix that for you. But excellent salespeople typically will talk well under half the time in a conversation because they're out asking questions, probing often helping a customer arrive at conclusions on their own. And so learning how to do five why's, go deep rather than immediately going into problem solving mode. If they ask a question, you respond often. If they ask a question, you should ask a question about the question and then respond. So learning to be great at that, I think differentiates people.

Lenny RachitskySo the last tip, I think there's something a lot of I bet everyone could learn is just listen more and talk less.

Jeanne DeWitt GrosserYep.

Lenny RachitskyOn that first piece of advice, this kind of sharing unique insights and how your suboptimal, is there an example you could share of how you did that? Maybe a story of just how you convinced someone you're selling Striper or Vercel like care or something you're missing. Here's how this could help you become much better.

Jeanne DeWitt GrosserSo with Vercel, sort of giving an example, but I'll make it more specific. So the performance point, you can go and look at core web Vitals, and so we can actually see the different things within their site that are fast or load correctly, et cetera, so anyone can go look that up. But what we can do is actually then help with benchmarking relative to peers. So that's been a big one that we've gone out and done. The other one that we've spent some good time on is just around helping customers understand MCP servers and when it would make sense to use one. So I think those are all the rage, but often people don't know how to contemplate them within their own product. So that was another one that we've gone pretty deep on and then related to, the first one is AEO Answer engine optimization is actually somewhat tangential to Vercel right.

So we drive performance, performance drives SEO. SEO is an input into AEO, but we have spent a ton of time sharing insights on AEO because we ourselves focus deeply on it and think we understand it better than many. And so again, as part of just building a trusted relationship, folks may go from those AMAs or that content into, okay, great, you taught me a lot and therefore I want Vercel to help me with performance. But in many cases, they actually now are just like, "This is a company that seems insightful, it seems like one I can learn from, and now I'm going to pay a little bit more attention to them." And over the fullness of time, maybe they see something that triggers them to decide, "Now is the time I want to go investigate that aspect of Vercel."

Lenny RachitskyAwesome. So what I'm hearing here in many ways, and this resonates, I had Jenna Abel on the podcast recently and it was all about sales skills and how to sell.

Jeanne DeWitt GrosserNice.

Lenny RachitskyAnd one of her tips is you don't want to be focusing on here's the pain and problem we're solving and instead focus on here's how you will be better than your competitors. Here's the big gap and alpha that you can achieve. If you use Vercel, you were missing out on speed and you're going to get screwed in AEO and all these things. Here's how you can architect your entire payments system to be top tier. Does that resonate?

Jeanne DeWitt GrosserYeah, I was told this stat. It's round numbers, so I can't imagine it's entirely accurate, but basically that customers, 80% of customers buy to avoid pain or reduce risk as opposed to the other one out of five to increase upside, which is a good thing again for startup founders to understand. So we all love to talk about the art of the possible, everything we're going to enable in the future. It's very exciting. Everyone's visionaries, but that's often really a sale that's going to resonate with another founder. And for everybody else, particularly enterprises, you're avoiding the risk of not making your revenue target next quarter, the risk of being outdone by the competition, the risk of having brand damage, et cetera. And so it's really hard actually for many startups to make that pivot because it feels off brand, but it does actually drive more buying behavior, is setting up a little bit of that concern that either I might not be well positioned or again through good question asking. I know exactly where I'm not well positioned and you can help me, that

Lenny RachitskyThat is such an important stat you shared. This has come up actually before in this podcast that buying, people are buying in large part to reduce risks, to basically not hurt themselves in their career, not hurt the company. That's a bigger factor in the buying decision than, "I have this problem I need to solve. And okay, thank you, this is solving." And the way April Dunford came in the podcast and talked about this of just like it's such a massive career bet. We are going to bring in product X and it's going to become, like Stripe, let's say, let's not talk about Versel. But let's say Stripe, we're going to adopt Stripe. That's a huge decision. If it doesn't go well, your career is hurt, your manager is going to be mad at you, it's going to set your company back. So a lot of the buying decision, as you've said is I just don't want to screw this up.

Jeanne DeWitt GrosserRight. Absolutely.

Lenny RachitskyOkay. Along the line of tactics, something that I know you're a big fan of and help people think about is segmentation.

Jeanne DeWitt GrosserYes.

Lenny RachitskyThis is something a lot of founders struggle with. They know, "Okay, I need to figure out my segmentation strategy and here where we're going after." Can you just give us a primer on segmentation, what people should know about why this is important and then how they might approach this.

Jeanne DeWitt GrosserSo segmentation is basically how do you carve up the world of companies that exist on the planet to reason about them where they buy differently? So I'll give examples from Stripe and Versel to bring this home. So a very typical company segmentation is small, medium, large. That's a rational way to do things. Small, you often have a single decision maker, medium, a small team, and large, it's complex, it's a committee, et cetera. So the buying process does change across SMB, mid-market enterprise, but if you stop there, you are likely missing. But what are the things within your offering that also change the way something gets sold? So at Stripe, there were two ways we further cut the business. Way one was, so think of segmentation as a graph. So X-Access was size, so small, medium, large, y-access was growth potential. And that was important for Stripe because it was a consumption-based business.

So if you were going to grow at 200% year-on-year, you were more valuable to Stripe than if you were going to grow at 8% year-on-year. And so we wanted to spend more time, spend more money going after the 200% growers than the 8%. So that was one that informed your strategy on who you targeted. And then for Stripe, the other thing that we cut it was business model. So are you a B2B? Are you B2C? Are you B2B2B, E.G. a platform or B2B2C, E.G. a marketplace and why is that relevant? Well, if you're B2B, you are going to need business payments. Credit card was useful for a PLG function or PLG sale, but you were going to need ACH wires, etc. And you probably had a recurring business, so you were going to want Stripe billing. If you were B2C, that's consumer.
So you're going to want consumer payments. Apple Pay is super important. If you were in the platform or the marketplace, you were going to buy our connect product. So it helped us basically then craft a more targeted and replicable sales. Vercel, sort of similar deals. So small, medium, large buying complexity. We also do the same thing on growth potential because we are similarly a consumption based business, but for us, a couple other things on the X-axis, we layer in promote, which is one of the things that is observable is traffic, site traffic on the internet. So Google publishes a Crux score, which is basically they have a bunch of data in Chrome, and so they know that Lenny's site gets a million XC amount-

Lenny RachitskyMillions.

Jeanne DeWitt Grosser... volume that Jeanne's site does. And so basically if you are a small company but you have super high traffic that's going to be more complex, Vercel is going to make more money and so we want to promote you.

So great example of this would be OpenAI. OpenAI, I forget these days how many employees it has. Let's say it's 3,000, it's probably more than that at this point, but so that's going to put it in the mid-market at most companies, but they're a top 25 traffic site on the internet. So for us, that's going to push them in our enterprise because we need to go lean in with a much more in depth sales process. And then the other thing we layer on is a workload type. So if you are an e-commerce company, that's going to be a very different sale. You actually use different language. You talk about product listing pages and product description pages, and you've got an order management system as the back end. Super different from a crypto company where you might be running soup to nuts on AWS. And so again, that helps us start to then have a really different buying content for you.

Lenny RachitskyOkay, this is awesome. So essentially what you do is you break up this universe coming back to your original story at Stripe to help you sort essentially which companies are most likely to buy your product. And what you're coming up with is these attributes that are correlated with they're likely to be great potential customers.

Jeanne DeWitt GrosserYep.

Lenny RachitskyDo you recommend using this XY axis as the approach versus something else? There's like a spreadsheet with five columns. I don't know, how do you start?

Jeanne DeWitt GrosserThere's probably something to be said for X and Y. like do you think size is going to play into most buying decisions and then these days there is a fair amount of consumption happening? So there'll be aspects of this that I think are somewhat universal. But I think basically when I came to Vercel, because new product market product offering, for me it's a new market. I had a lot to learn, but this is one of the first things I did in the first 30 days. And so basically I sat down with the gentleman Abhi who leads data science here and said, okay, what drives revenue? So what are the things that you can look at X ante about a customer to know this person's likely to pay us a hundred thousand dollars versus a million? That's probably going to be part of a segmentation framework. And then similarly, okay, what attributes would we look for to cluster where we seem to be winning repeatedly? And that was how we ultimately got at, okay, Crux rank is going to be super important because what you pay Vercel is correlated with your traffic. And then workload type was super important as well.

And for Vercel, when we did that, it was really interesting because we saw, wow, we have a lot of penetration and e-comm not that surprising actually, given that we drive highly performant sites and e-comm having a superfast performance site really matters. But at the time, if you looked at as an example, an enterprise SaaS companies, we didn't have a lot of penetration, even though you would've thought, okay, front-end cloud, very developer oriented. Of course software companies would be on us, but in enterprise, most of those companies built that SaaS offering before Vercel existed. So migrating 2 million lines of code to Vercel, that's a big lift. So it helped us really understand where are we winning, where are we not? And now as an example, within SaaS companies and enterprise, we're actually seeing a lot of interest in the AI cloud. Those are some of the earlier adopters of, "Hey, let's add AI native functionality to our existing SaaS app." And so again, it helps us figure out what to target where.

Lenny RachitskySo essentially you're doing this regression analysis on what's working and then here's the attributes that are most correlated with success. Something I always recommend when founders ask me for how do I figure out my CPE? How do I figure out where to focus, my heuristic is just think of three attributes that narrow them down. So it's like series A company that's angel-led, that's the marketplace, something like that. Does that feel like a good just rule of thumb just to start?

Jeanne DeWitt GrosserYeah, I think beyond three, that's getting pretty detailed and reasonably speaking, you're not going to cut. You have five sellers. So, what, you're going to put one seller in five different segments? So I do think three is something you can reason about. The other thing I'll say on this topic that I think is really important is a lot of times folks think segmentation is a go-to market thing. I really think it's a company thing. So when you Vercel, I actually deliver and every new hires first week, one of our company values is KYC, know your customer and I deliver the KYC section and talk through our segmentation framework how our customer base maps into those segments because it's really important as those new product managers leave the room that when they're building something, they think to themselves, okay, I'm building a new back end product. Who is this targeted at? Is it targeted at an enterprise or a startup? Basically, do I have a point of view on where I'm trying to win and why? And if you're doing that out of the gates, then it's much easier to then go speak the same language with the go to market org and figure out, okay, how are we going to take that to market in line with the other emotions that we have in play?

Lenny RachitskyOkay, this is a great segue to, there's a couple other things I want to talk about. One is something I've heard from so many people you've worked with is that you are amazing at building a go-to-market org that works really well with product and engineering. So I'll read this quote from your former colleague, Kate Jensen. She said that your superpower is building a sales org that doesn't feel like a sales org to engineers. So the question she suggested asked just what does it take to do that? What are the ingredients to building a sales org that engineers and product teams really like working with?

Jeanne DeWitt GrosserThe litmus test I have always given my sales team is if you are an account executive in my org and I put you in front of 10 engineers at our company, it should take them 10 minutes to figure out you aren't a product manager. And what I'm trying to get across is you need to have incredible product depth. And the reason for that is twofold. One, it gives you credibility with the product and engineering org. And two, I also believe that the best go-to-market orgs on the planet are equal parts revenue driving and R&D and D. And the reason I emphasize the latter is if you think about a product management organization, you may have a UXR team out doing research, product managers certainly should be out talking to customers. Well, if I have a 20-person sales team, think of the number of customers that we talk to in a week. And so if we can do an excellent job of translating all of that feedback into signal and then feeding that into the road map, we can be actually an extension of the product management org. But that takes being really good at discerning signal from noise, understanding when something is an objection that should be overcome versus an opportunity in the market. So I think those things have helped.

Lenny RachitskyI just love this as a product manager, maybe form a product manager. I don't know what the hell I am these days. I just love the idea of the salesperson. Like you not knowing the difference between a product manager and a salesperson. The most classic challenge is sales orgs ask for all these features and PMs are constantly having to push back and think about does this fit into everything. So it feels like that's a big part of this is to understand that deeply.

Jeanne DeWitt GrosserYeah, you want a sales org that can think like a general manager, so that's not just trying to get deals done but is trying to help build a business. And so again, knows when to say no, knows when to do objection handle versus knows, Hey, I've actually heard this on the last three calls and I do think this would be a really big unlock that would make us more competitive, would be something that new that nobody's doing. So I think that takes looking for a profile that both has sales skills but also is going to think with that product mindset.

Lenny RachitskyI love that. Okay, so another quote from Claire Hughes Johnson, former podcast guest, amazing sales leader, worked with you at Stripe. She said something along these lines, but a little different. Jeanne is probably the best go-to-market person at connecting with product and engineering, deeply understanding the product and providing the most valuable input to her counterparts of any I've ever seen. It sounds like just another ingredient here is just sales feeling like a real partner to product engineering actually, not just being like, "Hey, do these things for me, but actually feeling like a partner."

Jeanne DeWitt GrosserUltimately company strategy is basically product strategy meets go-to market strategy. And so I spend guess as a go-to market leader, I'm constantly trying to figure out how do I make more money more efficiently? And you typically do that by having a winning product in the market that is well commercialized. And so that means that I really lean into thinking about product strategy and thinking about pricing strategy because if those two things are optimal, you're going to win more often and there'll be less friction in it. And so that's sort of where got to put as a revenue leader, like a GM hat on and not just think, how do I sell? But actually how do I enable the insights I'm getting from talking to customers constantly to have the company strategy be more effective?

Lenny RachitskySpeaking of product, going in a slightly different direction, PLG product-led growth, it felt like it was very hot for a while where everyone's like, "You got to go PLG, that's the only way to win. It's impossible to do sales. The future is PLG." It feels like that's gone away. And in large part, obviously still companies grow through PLG and work through PLG. What's just kind of your thoughts on PLG and when does it make sense for a company these days to actually think this is how they'll grow for a while?

Jeanne DeWitt GrosserPLG makes sense for a lot of companies at the outset, unless you are very explicitly building a product for enterprise. So Sierra as an example, right? They are very clearly going after Global 2000 or something close to that. PLG is not going to be overly useful to them because they are trying to win eight-figure deals from day one. But for a lot of products, folks are targeting a startup audience at the outset and then they're adding more functionality so that they can ultimately continue to scale up market. So I think PLG is still super relevant. It's a major driver of Vercels growth. It was a big driver of Stripe's growth. The thing that folks get wrong is it does typically have a ceiling. So people are generally not going to give you $1 million via self-serve flow. So at some point if you want to sustain growth rates, you're going to have to have your deal sizes get bigger and bigger. And where I think folks get stuck is waiting too long on PLG because it does take a while to build a replicable sales process and a sales process, which often you're getting fed by inbound at the beginning and then you got to add outbound. It takes a while actually to turn outbound into a predictable engine. So I think where you see companies hit walls is just when they don't add the sales portion of it soon enough.

Lenny RachitskySo essentially every company ends up having to build a sales org, some start product-led and then at sales, some just start sales and have it from the beginning.

Jeanne DeWitt GrosserYeah, I would agree. There are probably some good examples of large vertical SaaS platforms that are SMB, but even they wind up with Velocity sales team. So yeah, I don't know that I can think of a 100 billion company that's PLG-only.

Lenny RachitskyYeah, it just feels like you're leaving money on the table even if you are growing really fast. I know Atlassian was a long-time PLG company but eventually succumbed. I don't know if that's the right way to put it. Okay. You mentioned pricing. I know you have strong opinions on pricing and pricing strategy. What's just a couple of tips you might share with someone thinking about how to price their product?

Jeanne DeWitt GrosserYeah, this is kind of on the theme, but I think the first thing is you got to think about pricing like a product. So it's another one where it actually really matters how you choose to price a product. Do you really understand where customers are going to drive value? Do you really understand where you incur costs? And are you doing a smart job of aligning those things? You've got lots of examples of companies grossly underpricing, you're sort of afraid to charge for the value that you actually provide. I think there are a lot of examples where people default to including a freemium strategy without that actually being a strategy. A good example at Stripe, we launched Stripe Billings years ago. It had a freemium strategy because that's what you do. And then we sort of looked at it and we're like, "actually integrating straight billing takes a little bit of work.So if you do that, you're probably going to stay."

And so we killed that, killed the free trial to zero downside. So that's another one. At Vercel, we've been going through that transition where we're a consumption-based business model ultimately, but at the outset we basically kind of bundled that into what looked like a SaaS-like price and as we've added a lot more functionality that wasn't working anymore. And so we did an unbundling and right now actually we did a pretty substantial pricing change in August where we have an enterprise at a pro-skew. And if you looked at the enterprise skew, it's called Enterprise for a reason, enter, it's meant to be sold to an enterprise. And actually about half of the folks on the enterprise skew were startups, which suggests that there's stuff in the enterprise skew that a startup really wants. So we kicked a lot of that stuff out of the enterprise skew and made it so you could buy it self-serve online and what do you know, people are.
So now that's really driven a lot of growth in our PLG funnel, which is awesome for startups because it's super efficient. They can just buy things, they want that. It's awesome for us because you don't have to have a human intermediate that. So getting all of these knobs really tuned is a key to both a great customer experience and optimal revenue outcomes.

Lenny RachitskyMaybe just one more question before we get to a very exciting lightning round. It's going to be a combo question. I hear you have a hot take on sales comp, how to comp salespeople that's different from other people and also who to hire when you're hiring folks in sales. Can you just talk about your takes there?

Jeanne DeWitt GrosserI struggle with sales comp because it's all about pay for performance, which I'm obviously a fan of, but it makes your organization less flexible because you basically have to decide 12 months in advance, these are things I value and particularly in this moment that could be different. As a great example of this, when we wrote the sales plans for this year at Vercel, the AI cloud did not exist. We were selling our front-end cloud and we were selling VZero and introduced the AI cloud halfway through the year. Now we had all sorts of good ways to still incentivize that, but I think you want to be able to be innovative and pivot and when you have a well-designed sales plan or a very structured sales plan, that can be challenging.

So that's a little bit of my hot take is just I'm trying to figure out how do you have the upside of sales of motivates people. It's a quantitative function, which is great, but also the flexibility to change your mind because I think a lot of companies right now are having a hard time doing annual planning. So that's one. On profiles, I have always valued just sort of a diversified portfolio. So I strongly believe that sales is a skill and so you want salespeople with actual sales experience in your organization, but I think there's value in pairing them with more nontraditional backgrounds, in particular consulting or banking background. Those folks are really good at more quantitative and analytical aspects of sales. So getting into that consultative part, which I think we talked about at the outset. And so I find that when you mix these together, the sort of consultant banker profile realizes, "Oh wait a minute, sales is a skill and I didn't really have it." And so they go learn from your account executives with that background and then your AEs learn more about, okay, how do I think about a P&L? How can I talk to a CFO? How do I present a TCO analysis more effectively? And so just creates a much richer learning environment where people are bouncing ideas off each other.

Lenny RachitskyThat is awesome. I love that strategy. Okay, final question. Just is there anything else you wanted to share? Anything else you want to leave listeners with before we get to our very exciting lightning round?

Jeanne DeWitt GrosserOh man. I feel like we've been very thorough.

Lenny RachitskyAll right, thanks So too.

Jeanne DeWitt GrosserYeah, you stumped me on that one.

Lenny RachitskyOkay. That's the goal. With that Jean, we've reached our very exciting lightning round. I'm going to make it very quick. I know you got to run. I'm going to ask you just two questions.

Jeanne DeWitt GrosserOkay.

Lenny RachitskyOne is I'm going to skip to your life motto. Do you have a favorite life motto that you often come back to find useful in worker and life?

Jeanne DeWitt GrosserI do. I actually have found that I'm known for saying a handful of things that I didn't necessarily realize it, but when you leave an organization, people tend to tell you what stuck with them. But there is one that I think I am known for saying growing up, my mom always said to me, when the going gets tough, the tough get going. And in sales, you're always going to have a quarter when you're not on pace. And so that's one that I feel like I pull on, not infrequently because in my view, there's another version of this, my mom also always says was where there's a will, there's a way. So I think you can always choose to find a path forward even when that's not super clear.

Lenny RachitskyI love these. Okay, last question. I read that you were a very competitive diver in college early on. I'm just curious if there's something you learned from that experience that brought with you that helps you be as successful as you've become?

Jeanne DeWitt GrosserWell, I mean, first of all, I should say I was generally coming in third place out of three on my team.

Lenny RachitskyThird place, that's not bad.

Jeanne DeWitt GrosserI managed to do it in college, but that was the extent of that career. So diving is a precision sport and it is a repetitive sport. And it is also a sport where when you land flat on your back, and literally as you are swimming to the side of the pool, welts are forming on it, you always 100% of the time will be forced to immediately get back on the diving board and do that exact same dive again. And so I think that has a lot of stuff that's transferable to work and to sales. So for me, I just have an obsession with excellence and within sales. sales is about replicability. How do you drive predictable outcomes, how excellent are you at your ability to forecast? And so I think I bring that to bear within sales a lot. And then similarly, you get a lot of nos in sales. So another phrase that a sales guru said to me once or in a training was yeses are great, nos are great, maybes will kill you. And so how do you get really comfortable that no is a great thing and that just gave you data and now you can go do something with it.

Lenny RachitskyThis is a really inspiring and empowering way to end the conversation. Jean, thank you so much for being here.

Jeanne DeWitt GrosserThanks so much for having me, Lenny. It was a lot of fun.

Lenny RachitskyBye, everyone.

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

Lenny RachitskyI've been getting so many asks for go-to-market help.

Jeanne DeWitt GrosserWith AI, it's just intensified because you have 10 players pursuing the same market opportunity and so your ability to actually bring the product to market to differentiate yourself from the competition has become more strategically important than it was previously.

Lenny RachitskyI had Jenna Abel on the podcast recently, one of her tips is you don't want to be focusing on here's the pain and problem we're solving and instead focus on here's how you will be better than your competitors.

Jeanne DeWitt Grosser80% of customers buy to avoid pain or reduce risk as opposed to increased upside, which is a good thing for startup founders to understand. We all love to talk about the art of the possible, everything we're going to enable in the future, but that's often really a sale that's going to resonate with another founder. For everybody else, particularly enterprises. You're avoiding the risk of not making your revenue target next quarter.

Lenny RachitskyI've heard a lot about how you think about go-to-market as a product.

Jeanne DeWitt GrosserWe buy a lot of things because of how we feel about them. The experience that you have of being sold to will increasingly actually differentiate a company and drive buying decisions if products are only different at the merchant. And so then you really want to create a customer buying journey that feels like very unique experiences.

Lenny RachitskySomething I've heard from so many people you've worked with is that your superpower is building a sales org that doesn't feel like a sales org to engineers.

Jeanne DeWitt GrosserThe litmus test I have always given my sales team is if you are an account executive in my org and I put you in front of 10 engineers at our company, it should take them 10 minutes to figure out you aren't a product manager.

Lenny RachitskyToday my guest is Jeanne Grosser. Jeanne was chief product officer at Stripe where she built their very early sales team from the ground up. She's currently COO at Versel where she oversees marketing, sales, customer success, revenue ops and field engineering. Jeanne has built world-class go-to-market teams at multiple unicorns and has advised dozens of companies on doing the same. In our conversation, we go deep on what a world-class go-to-market team looks like, including what the heck is go-to-market, the rise of the go-to-market engineer and how this role is already enabling her team to operate 10 times faster. A bunch of very specific tactics to level up your go-to-market skills, a primer on segmentation, how to think about your go-to-market process like a product, her favorite go-to-market tools, her hot takes on PLG and sales comp and sales hiring, and so much more. If you are looking to get smart on the latest and greatest in go-to-market thinking, this episode is for you.

It starts with product analytics where PMs can watch replays, review funnels, dive into retention, and explore their growth metrics. Where other tools stop, Datadog goes even further. It helps you actually diagnose the impact of funnel drop-offs and bugs and UX friction. Once you know where to focus experiments, prove what works. I saw this first hand when I was at Airbnb where our experimentation platform was critical for analyzing what worked and where things went wrong and the same team that built experimentation at Airbnb built Epo. Datadog then lets you go beyond the numbers with session replay. Watch exactly how users interact with Heatmaps and Scrollmaps to truly understand their behavior. And all of this is powered by feature flags, that are tied to real-time data so that you can roll out safely, target precisely and learn continuously. Datadog is more than engineering metrics. It's where great product teams learn faster.
Jean, thank you so much for being here and welcome to the podcast.

Jeanne DeWitt GrosserThanks for having me. Lenny.

Lenny RachitskyWhat I wanted to get out of this conversation by the end of this to basically have this conversation be the thing that we send people when they're like, "I want to get better go to market. I'm trying to figure out what to do and get to market." We send them this versus having to hire someone for a lot of money and usually they can't find amazing people, because they're all snatched up. So let me start with just the basics. When people hear at the term go to market, what does that mean? What does that encompass?

Jeanne DeWitt GrosserI think there are two answers to this. Often what people think of is sort of the tip of the spear of what drives revenue, which is marketing and sales. For me, I think of it as any function that is going to touch a customer or make a dollar, and actually my remit at Vercel is that, so that includes marketing, sales, all of your technical sales roles like sales engineers or post-sales platform architects is what we call them at Vercel. It's customer success, it's support, it's partnerships. And the reason I say that is my experience throughout my career has been that those functions often have this Venn diagram strategy where marketing's pursuing one thing, it overlaps with what sales is pursuing, but not perfectly, which also overlaps with what support is pursuing but not perfectly. Examples of this would be slightly differing segmentation frameworks, et cetera.

And so one of the things I think you're going to want to see more in this particular moment is that that become a really integrated lifecycle. In particular, I think we're going to see a lot of the functions of go-to-market get redefined, so we've gone through a period of hyper-specialization in go-to-market depending on how you count them. There are, I think somebody quoted 17 different roles within go-to-market these days and I hypothesize that a lot of those are going to start to collapse. And so if you think of go-to-market more holistically, I think you can kind of go back to what are the jobs to be done from making a customer prospect aware of your product all the way through to high LTV, five years on the platform, fully wall-to-wall, and you're going to want to map that out and orchestrate it the way you would think about that within your own product.

Lenny RachitskyAwesome. We're going to go through that whole cycle of go-to-market, but so is it safe to say just for most companies that are especially starting out when they say go-to-market, that mostly is sales and then there's marketing as maybe a smaller fraction of that and then as you become more advanced and grow, customer success plays into it, tech sales, things like that?

Jeanne DeWitt GrosserYeah, that's probably where most start is getting sales or frankly just because a lot of companies also start PLG, you might actually start with marketing and then you're layering in sales when it's time to do the sales assistant and ultimately sales led portions. So I think it can, depending on your product and your initial target market, it can either mean marketing or sales or a combination of those two.

Lenny RachitskyAwesome. So essentially it's like the term go-to-market tells you what we're talking about. How do you take your product to market, get people aware of it, using it, sticking with it?

Jeanne DeWitt GrosserYep, absolutely.

Lenny RachitskyWhat has most changed in the world of go-to-market over the last few years? You've done this for a long time at Google, at Stripe, you built it for sales team, now you're doing that at Vercel. What's changed most in the skill and art of go-to-market?

Jeanne DeWitt GrosserThere are a number of things. So when consumption-based business models started, I think you saw go-to-market shift into being meaningfully more consultative because often that first land was the very beginning of the journey and represented a very small percent of what you were ultimately going to do with that customer. And so you had to go from being transactional to a lot more. You had to more deeply understand what that customer was trying to do so you could align that ultimately to your product. I think that has played out that much more with an AI because right now everyone knows they need to change, but they don't necessarily know exactly what they need to change to, whether that's their customer-facing product or their internal productivity and workflows. And so I think you're seeing a lot more of go-to-market orgs leaning into the art of the possible best practices, helping you actually think things through as if they were a consultant.

And so one of the things you see more of right now is forward-deployed engineering, which on some level is kind of a rebrand of professional services but kind of not. And a big part of that is, hey, how do I actually get into your environment, ride alongside you better understand what you're trying to do and then help you actually bring the technology to life and learn a lot along the way.
Often you're not only making that customer successful, but you're then taking all of that back to your product and engineering organization to figure out, okay, what was generalizable that we ought to build into our offering versus what is something that ultimately is going to be more of a professional service in the fullness of time. So I think that has been a biggie, is actually just really getting embedded with your customer. And then unsurprisingly, I think bringing AI to bear on the sales process is another big one. And so you've seen the rise in probably the last 18 to 24 months of the go-to-market engineer, which different folks define slightly differently, but it's kind of bringing one technical prowess to bear on go-to-market in general so you can have a lot better tooling, data use, et cetera. And then two, increasingly bringing AI to bear as well to re-architect your workflows and also make it so that it's easier to have a personalized experience with customers but do so at scale.

Lenny RachitskyAmazing. Okay, let's follow the thread on this go-to-market engineer, so what was it like before and what are these engineers doing at companies?

Jeanne DeWitt GrosserSo I think maybe an interesting story to tell. When I was at Stripe, we went to launch an outbound SDR function. So outbound prospecting and Stripe always ran lean. The company at that time had an operating principle which was efficiency is leverage. And so if you looked at the sales organization I was running, most companies out there probably would've had 30 SDRs and I was going to get four. So there's no way I was going to do the typical SDR approach and be successful. And so we thought to ourselves, okay, what can we do? We'll be super data-driven. And so we went and we started building project Rosland. Rosland is the scientist who originally mapped A-DNA. And what this was was effectively a company universe. So you can think of this as a massive database. Every row was a different company on the planet and every column was an attribute about that company that would help you sell to them in a more targeted fashion.

So at Stripe an example would be knowing that their business model was a marketplace was super helpful, because that would mean you wanted to sell Stripe Connect versus vanilla payments. And so the goal was basically, hey, can we create a mad Libs where I will come up with sort of a predefined email template, but 80% of it will be fill in the blank based on the different attributes of that customer. So if they're this industry or this business model, then pull this customer, reference this value prop, send it to this persona, not that. And we were trying to do this in 2017 and it was very hard and didn't actually totally work our ability to the false positive rate and we worked deeply with DSI and it just never really got there. And now that we're literally redoing here at Vercel as we speak and it actually works and you can bring AI to bear on it.
And so what's different is we now, I have a data scientist just like I did back in 2017, but I have a go-to-market engineer whereas before I just had someone in systems that was helping me configure outreach or sales off and my go-to-market engineer is helping me build an agent where we're coming up with, okay, well what's the human workflow that you would've done? And then how do you encode that using Vercel workflows as an example in actual code that's both deterministic and less so where an agent's going out and trying to replicate what a human might've done to produce that, fill in the blank, matlit.

Lenny RachitskyI love the ambition of that project. What is this, like eight years ago?

Jeanne DeWitt GrosserYes.

Lenny RachitskyI love the big thinking there. We're going to map the entire universe of companies and then here's how we sell to them. And then just I'm trying to picture doing that without AI. It's like crazy to imagine trying that without AI and that's so much simpler to even imagine.

Jeanne DeWitt GrosserWell the thing that's amazing about that, just to geek out on a second, so I was working on that with a bunch of folks at Stripe on my team, obviously at a gentleman named Ben Salzman who went on to go to ZoomInfo and then actually recently just founded a go-to-market startup that is basically sort of productizing that concept of a company universe and then layering AI on it on top of it. And ultimately his view is actually AI will get to the point that you won't have to do outbound prospecting because it will just sort of company and product match. So it's fun to sort of see back in 2017 some of the folks doing that now work at OpenAI, they work at Anthropic, they also are doing GTM Eng. You've got him starting a totally AI native GTM company and then here I'm at Vercel trying to do the same.

Lenny RachitskyOkay, so what's cool is this is an emerging role, an emerging skill that I don't think a lot of people have recognized as something that is happening. So one example I'm hearing of what this role does is they automate outbound emails essentially and outbound outreach. They figure out, they write workflows and agents that figure out here's the company to go after, here's how we message them. Does that end up being kind of like an email that's custom designed and written for this prospect?

Jeanne DeWitt GrosserThat's one version. So it's broader than that really. Basically the full remit of GTM Eng will be to go through each of the different functions within go to market and break down all the different workflows that they do and then turn those into agents where AI is better placed than the human to do that task. So right now we started with actually inbound and are now moving to outbound because that workflow is most legible. And by legible I mean you can basically write it down. It's relatively replicable, mostly deterministic. So it's more likely that AI will do it well and we actually built the agent and then we keep a human in the loop. But from there we're starting to look at outbound and with an outbound we're starting more at the lower end of the market, where you tend to have slightly less customization because there's a single decision maker at the company.

But I think it'll take a while before we're able to really do that in a very large enterprise. There we might use an agent for research but maybe not all the way to actually send a message and that's just within the prospecting function. So other places that we're looking at this would be for install-based sales. So again there it's a little bit more deterministic because you've got awesome internal data on what a customer is and isn't using, what's the next best action? What's the thing they should get most value from? So that's where we're starting to map, hey, what does that ideal workflow look like? But basically you want to get to a state where as long as I've been in sales, they release these annual reports that help us all benchmark ourselves relative to one another. And one of the stats is what percent of time do your sellers actually spend in front of customers?
And for the 20 years I've been in sales, it's always been somewhere around 30% to 40%. So the minority of time is actually talking to other humans and I think we're getting to a point where with layering in agents, ideally we finally get salespeople to a point where they're actually spending 70% of their time interacting with humans and we can get the research, the follow-up, the things that are a little bit more rote and don't use the entirety of your human capacity done by an agent and then sort of unleash you to go deeper with your customers.

Lenny RachitskyI love that this is such a great example of where AI is contributing in a very meaningful high ROI way, taking on all this work that people... like, you have to hire say 50 SDRs as you described to do and now you could do with a lot more. So it's a really cool example of leverage that AI gives you. One thing that I know a lot of people think about when they hear this is, okay, I'm going to get more of these really bad emails trying to pitch me on stuff and just like this isn't going to work. I can tell this is AI. What have you learned about how to do this where people actually receive emails that actually convert and do well?

Jeanne DeWitt GrosserOur processes all always have human in the loop. And so basically where we'll start is we take a go to market engineer and we have them shadow the highest performing individual in that function. And so you can go and you shadow an SDR and you can see, oh wow, they've got seven tabs open. They're looking up the person on LinkedIn, they're reading about the company, they're doing chatGPT on this, they're looking in this database to get these sets of attributes. And so that's how you sort of inform the initial workflow. And then what we do is we let the agent make a call. So in the specific example with inbound, you have to determine whether or not you think the lead is likely to be qualified and then you have to determine what to say to it. And so we'll let the agent make those two calls.

It ultimately then does some deep research, pulls in a bunch of information from our databases and crafts a response, but we have a human review all of those and actually hit send. Now for us, we had 10 SDRs doing this inbound workflow and now we just have one that is effectively QA-ing the agent. The other nine we deployed on outbound, so we got to move them up the value chain. At some point I think we'll get to a place where we feel like, "Hey, the human reviewer is saying yes enough of the time that we feel confident that these will be on brand targeted, et cetera," but right now we're still trying to train the agent and it incorporates feedback on what we choose to reject, edit, et cetera.

Lenny RachitskyAnd you shared that it's already having a lot of impact. Like you said, you had 10 SDRs and now one can do the job of 10.

Jeanne DeWitt GrosserSo before we did that move, I mean the other thing that's just incredible about this is the person who built the lead agent was a single GTM engineer. He spent maybe 25-30% of his time on this. It was six weeks before we felt confident going from 10 to one. So it wasn't like this was a multi-quarter process, it actually moved super quickly and then again now we just sort of keep that agent manager working with the agent to get it to a point where we say, "Hey, we're ready to roll." Actually throughout the process we also tracked all of the KPIs that you typically would hold an SDR accountable to. We were looking at our lead to opportunity conversion rate, we're looking at the number of touches it takes the time to convert, and basically what we were able to do is hold that lead to opportunity conversion rate flat. So the agent is as good as our humans were, but it's actually condensed the number of touches it takes to convert because it's so much quicker at responding relative to leads inevitably sitting in the queue or coming in at nighttime and no one can get to it, that type of deal. So that's sort of when we knew it was ready to pull nine people off and shift them into outbound.

Lenny RachitskyThat's incredible. Okay, that's interesting. So you shift them to outbound. What I love about this is this SDR that is now doing this is, as you said, doing the things they enjoy more, they're talking to customers more, they're not doing all this kind of top of funnel rote work. I don't want to get into whole jobs AI discussion, but there's always been this talk about AI SDRs basically replacing SDRs. It feels like that's one thing where everyone's like this is a hundred percent going to be AI in the future. What I'm hearing here is it gives one Aster a lot more leverage and obviously you still need people running the show. Thoughts there? Just like do you think AI will replace all this at some point? And then I don't know, you don't need salespeople?

Jeanne DeWitt GrosserI think on prospecting it can replace a fair amount because the average SDR wasn't doing overly sophisticated research in the first place. So where I, think the last part to go as I mentioned will be in deep enterprise prospecting where you can be at multiple layers in an org chart, you've got to pick between business lines, you've got to triangulate those. But I do think for the things that are more repetitive that often don't take that much time to learn and get ramped, AI will be good at that. And in my view, no one graduated from college and was like, "Yes, I just went to college for four years to become an SDR." It was more, "Okay, that's where you are forced to start." But I think the average SDR could have gone straight into outbound or straight into an SMB closing role. And so basically what we're just doing is shifting folks into something that uses more of their full capacity right out of the gates rather than sort of the forcing function of working your way up the totem pole.

Lenny RachitskyAwesome. Since a lot of people listening to this aren't salespeople don't have a lot of background in sales, we've used this term SDR, there's also the term AE. Can you just help people understand what is an SDR, what do they do, what's an AE, and then what's the role above?

Jeanne DeWitt GrosserSure. So SDR is typically in charge of generating pipeline. They're meant to talk to prospective customers and get them to a point where it is worth investing time to run them through a sales process. You typically have two types of an SDR, have an inbound one. So this is where people come to your website, they fill out contact sales, they'll be the first call to make sure that it's actually worth a more expensive account executive to go and run a sales process or you then have outbound. So this is where when you want to grow faster than your inbound demand, they will go out and at this point you probably have a point of view on where you think you have product market fit. And so they will target that part of the market and try to drum up interest from folks who weren't otherwise raising their hand saying, I'd like to talk to you.

So that's sales development basically. Pipeline generation account executives are closers. So it's their job to take somebody from, "Okay, hey, I'm interested in learning about your solution, I have a legitimate problem. I potentially could make a decision," to, "I now believe that your product is the best in the market for me and I'm willing to pay for it." And then account executives, depending on the segments that your company sells into E.G. small business, mid-market enterprise, et cetera, they may work their way up the food chain from selling to a smaller company like an SMB or a startup. Those tend to be a little bit more of a transactional sale. You often have a single decision maker to then going into a mid-market or a commercial role where now maybe you have an economic buyer like somebody in finance and a technical buyer like somebody in engineering to getting into enterprise where you have procurement and you have committees and 10 people have to weigh in and you've got to help them figure out how to de-risk the fact that they're probably migrating from something so much more complicated coordination effort to sell.

Lenny RachitskyThat was extremely helpful. So SDR, pipeline generation, i.e., closer. Such a simple way of thinking about it. Okay, this is great. Going back to the GDM engineer, a few questions for people that may want to try this at their company, what scale do you think it makes sense to start hiring for this role? Having someone automate in the go-to-market process?

Jeanne DeWitt GrosserWhat's interesting about this is it will force companies to be more rigorous about their sales process early. So often startups when they go from founder led sales to say, I'm going to have my first sales person, whether that's an actual account executive who has sales experience or your general athlete, wicked smart, who's going to go figure it out. Often founders will just say, "Okay, sales is showing up and talking to people. Isn't that what I just did for the last couple of years?" But actually sales is more than that. It's a skill just like writing code as a skill or building a financial model as a skill, it's about discovery. So asking all the right questions that help you identify challenges in pain, willingness to pay, et cetera, and then going through a process to handle those objections and showcase where are you at enough value such that somebody ultimately wants to hand over some money.

So often startups will get, particularly ones with strong product market fit to pretty significant scale without really having a replicable process. And you can't really apply go to market engineering unless you actually have a point of view on what best practice should look like. And so I think basically this is going to force folks to have more of a playbook out of the gates, what's working, what's not? Can I document it? Do I have content for the different parts of the sales process? And then once you do that, which maybe 10 people is a good size and scale for that, ostensibly a GTM engineer can come in and turn that into an agent. You could also argue that if you're a founder who wants to bring in a general athlete profile and that person is technically minded, that you could have a hybrid AE GTM engineer who figures out what their best practice is and then tries to turn that into an agent that's riding alongside them and making them more effective as well.
So I don't know that I have a point of view yet on what's the optimal size and scale, but I forever have given founders the advice that you often want to bring in revenue operations, which is basically the analytical arm of sales earlier than you think because having data, having process is actually what gives you insights as a founder into what is and isn't working. And so I would argue just like it's a good idea to have that sooner than later, increasingly it'll probably be a good idea to have GTM engine and be looking to bring agents to bear on your process at the outset.

Lenny RachitskyWhile we're on this topic, just a quick tangent, the advice for hiring your first salesperson that I usually hear is wait until you're around a million in ARR. When you have a repeatable process, you can teach someone anything there. Does that seem right? What would you recommend?

Jeanne DeWitt GrosserYeah, I think that seems about right. I do think as a founder you want to stay deeply connected to customers and get it to a scale and get it to a point where you use the word, there's some repeatability there. I think that's one of the things that not all founders get right is founders are incredible salespeople. They convinced a VC angel investors to fork over a bunch of money, so clearly they're going to inspire people to buy. But if you're getting to a million in ARR and the set of customers you have look nothing like one another, you still have very much like an evangelist sale, very much founder led sale versus if you can say, "Hey, I now have an ICP here, or ideal customer profile, e.g something you can write down. We are good. Our product fits with startups with less than a hundred employees who are typically building SaaS applications," something like that.

Then you're probably ready to hand over the reins. And then what founders have to remember is to actually hand over the reins. So you've got to enable the person who comes in, what is it that you're doing effectively, what's your content, what are the discovery questions you are asking? How are you handling objections so you can transition that knowledge but also don't handle them over entirely. You want to stay connected to the customer because you still have a fair amount of R&D to do to figure out where is the product next going to resonate, where are you getting stock as you scale, etc.

Lenny RachitskyTo close the loop on the go-to-market engineer, what's the profile of the ideal go-to-market engineer, may be your first.

Jeanne DeWitt GrosserWhat we have found works really well is somebody who does have go-to-market experience. So at Vercel, our first three go-to-market engineers we're actually sales engineers. So Vercel hires very technical sales engineers, all of them were front end developers before they decided they wanted to get into sales. And so we just said, "Hey, three of you, congrats." You're now founding members of our GTM Eng team. And the thing that works well there is you do understand aspects of what is good GTM, what does a process look like? It's been really interesting actually. So the gentleman who runs GTM Eng for me, we were going through this lead agent and QA-ing it. And so I'm going and I'm looking at some of the responses that we've ultimately had the lead agent send and realized, "Oh, I wouldn't have sent that and that's because I have 20 years of sales experience and we modeled the lead agent off our best person, but our best person who has two years of sales experience." So it actually is important to understand the art and the science of sales and how you bring best practice to bear. Either you've done it and so you know some best practice or you're going to geek out on sales, read a bunch of books, learn a thing or two, and try to incorporate some of those into your agent development.

Lenny RachitskyThat is really interesting. So come from the sales side, not from the engineering side. And I imagine this is such a cool opportunity for salespeople to do something completely different and move closer to engineering.

Jeanne DeWitt GrosserYeah, I mean we're having a lot of fun with it. At Vercel in particular, we basically get to be customer zero. So everything that we're building with agents, we're building on Vercel's AI cloud. So these agents now have multiple steps that they go through. So we're using Vercel's workflow SDK and workflow offering. We use the AI gateway to call the different models that we use to do deep research or other enrichment that we do. So for us it's great because we basically sort of bang on everything the engineering team is building and get to go be a discerning customer before we actually get it out the door to real customers.

Lenny RachitskyWhat a fun time to be alive. I could tell the fun that you guys are having, just from the way you describe it.

Stripe handles the massive scale and complexity of many of the world's fastest growing enterprises, including 78% of the Forbes AI 50 and more than half of the Fortune 100 enterprises like Atlassian, Figma and Urban Outfitters use Stripe to create fully branded and customized checkout pages with access to more than 125 global payment methods. There's a reason I've had more leaders from Stripe on this podcast than any other company. They know how to build great products that scale and that people love. And Stripe is a lot more than payments. They've also got a category leading billing solution and a highly optimized checkout experience built specifically to increase your checkout conversion. Join the ranks of industry leaders like Salesforce, OpenAI and Pepsi that are using Stripe to grow faster and to grow the world's GDP, learn how Stripe can help your business grow at Stripe.com. Zooming out a little bit in terms of you mentioned tools and tools that you use. I'm curious just what are kind of the state of the art tools within the go-to-market stack that you love that you'd recommend?

Jeanne DeWitt GrosserWell, so I'm going to have an interesting answer to this, so I'll give you one. And it's not state-of-the-art per se, although I don't mean that disparagingly, it's just that it's been around for a while now and a lot of folks use it, but I think Gong has gotten just meaningfully more interesting in the last year. And then second half of my question I will get into, I think the calculus on build versus buy is changing. So all right, Gong. Gong is incredible because you can run agents against it now. So we take all of our Gong transcripts and we dump them into an agent called the deal-bott, and that deal-bott then can do a bunch of things. So the first thing we had it do was lost opportunity review. So we had just finished Q2, we had a list of our top losses for the quarter sorted by deal size, and we ran it against that and it was incredibly interesting.

So the biggest loss that quarter according to the account executive was lost on price. And when you ran the agent over every Slack interaction, every email, every GONG call, it said actually you lost because you never really got in touch with an economic buyer. And when you talked to somebody about ROI and total cost of ownership, it was clear from their reaction that they didn't really buy your mass. And so really the reason we lost was an inability to demonstrate value, which upon reflection I've got work to do to build out how we quantify the value of Vercel, which actually is very easily quantifiable. It's one of the things I love about selling this product, but we got to codify that for the go-to-market team. So that was incredibly interesting and now we run it against all of our lost opportunities and actually do a much better job of categorizing why it was we really, really lost.
And then either feeding that back into the engineering team or back into marketing sales leadership on, hey, where are we falling short in the sales process? And so that was awesome, but then we're like, well, it's not very fun to lose, so why don't we pull that forward? And so we went from lost bot to deal-bott and now the deal-bott is running in real time and we basically feed insights into Slack. Vercel is incredibly heavy users of Slack, so we have a channel for every single customer, either opportunity or existing one. And so now we're feeding insights into that Slack channel which is, "Hey, you're this far into the sales process and you haven't talked to an economic buyer, you should think about that." Or, "Hey, you just got off that call with an economic buyer, didn't sound like it went that well. Here's some things to consider and how you might follow-up."
And last thing before I pause, the other thing that's really interesting and how we're using this too is we are in this moment where I have never seen an iteration velocity exists now in my career. My 20 plus year career has all been in tech. And so for go-to-market teams, that's really hard. If you are launching something every other day, the ability to be enabled on that is actually quite challenging. And so this bot agent is now also letting us, where we're starting to go with it is we'll release something, we'll do our best to enable the team, then we'll go run the agent across calls, interactions, and we'll diagnose where we did a bad job of objection handling, where we're getting stuck. And then at the end of the week we can have a huddle and say, okay, what are all the places that our agent would suggest we aren't selling effectively?
And then almost like an engineering team, we'll now run sprints, which is like those are just bugs. They're bugs in your go-to-market process, so you should not have them. And by the next week we're going to add content to our objection handling to guide. We're going to add content to a discovery guide, we're going to figure out something we need to change about our demo, so on and so forth. So that's early. That's a little bit of a preview, but that's where we're talking about taking things right now within our go-to-market orgs.

Lenny RachitskyJeanne, you're blowing my mind in so many ways, it just sounds so fun and just you guys are going to win is what I'm feeling when I hear all this. Incredible. What I love about this is this AI tool, this agent you built sees things that humans were not seeing. The fact that you were surprised of just like this is a completely different conclusion is such a big deal. This is the whole promise of ai, it's going to do things we aren't even thinking about or capable of.

Jeanne DeWitt GrosserIt is. We had a really interesting, one of the things we're doing at Vercel, we have an AI cloud, so people use that to put AI-native features into their customer-facing applications, but they're also using it to build internal applications to improve productivity or outcomes. And we are talking to a very large airline and that airline obviously gets tons and tons of support queries. So of course they would want to go apply AI to hey, how can we have AI answer these so that our cost to support goes down, sort of the obvious thing. But the more interesting conversation was actually with one of the C-level executives who said, we also actually transcribe every single one of those support calls. And so what I really want to know is why are they calling and how do I make it so that fewer people call the next week? And so again, this is now with AI, you can rapidly go through all of that content and actually be able to much more quickly than having a human in your CRM sort of pick some status why it was that folks were calling the airline this week and what if anything you can do to make it less the case next week.

Lenny RachitskyI imagine many people hearing this are like, "I need one of these deal-botts and lost bots." These are all internal products that you all built?

Jeanne DeWitt GrosserYes.

Lenny RachitskyIs there anything that you've learned about making them this good? Any tips you can share of here's how to make a really good bot for sales?

Jeanne DeWitt GrosserYes, so actually that's the second half of my answer that I forgot.

Lenny RachitskyThat's perfect.

Jeanne DeWitt GrosserWhich is sort of like bill versus buy calculus. So I think one of our learnings is that it's not that hard to build these agents and they aren't that expensive either. So I mentioned the lead agent that was a six-week process with one human, a third of his time, that deal-bott, the lost bot version was two days basically we riffed on it, he had it 40 hours later. Now we're continuing to refine it for the other things I mentioned. And what's also interesting about them is they for better or for worse for Vercel, but that lead agent which runs full stack on Vercel, will cost us about a thousand dollars to run for the entire year. If you remember I told you we had 10 people in the SDR function, so I'm paying well over a million dollars for that from a salary perspective.

I got that down to one. And then behind that I have a lead agent that costs a thousand bucks. So that's like a 90%-plus reduction in total cost there. And there's lots of software for agents out there right now. And I think one of the things we're learning is because this whole space is so nascent, often your own esoteric context, your content, your workflow is really key to unlocking the power of the agent. And so I think there's real value in experimenting with your own internal agent development. We may ultimately end up on better integrated agent platforms in the fullness of time, or we may find that the CIO increasingly goes from a procurer of software to a builder of software and you'll have an AI internal platform with a thousand agents running across your org. I'm not really sure yet. But I certainly think there's value in trying it yourself because you may find that it's meaningfully easier than you think and you get returns pretty quickly.

Lenny RachitskySo what I'm hearing here is that you're finding that there are not tools out there to plug and play. The alpha is essentially in building your own stuff.

Jeanne DeWitt GrosserI think that's partially true, and I think because you also have all these tools proliferating right now, you get into the perennial problem where you wind up with 20 of them to do the 20 jobs to be done basically, rather than an integrated platform that's doing all of them. I'm hearing this a lot actually when I'm talking to customers right now where their biggest issue in deploying AI is actually just getting through procurement and it's because got an AI mandate, you kind of have a blank check. I recently heard the term of instead of ARR, it's ERR, which is experimental run rate revenue, which is to say everyone's out there sort of, Hey, we're going to give this thing a go for a year and then TBD on whether or not we keep it. But basically you're having to procure 20 different things. Most things are getting off the ground and so they're solving something relatively narrow and that'll change in the fullness of time. But I do think there's an opportunity to figure out, hey, where do I likely have a more specific workflow internally. For that it might be worth building your own agent and then maybe for the things that are a little bit more generalizable, you go get something off the shelf.

Lenny RachitskyAre there any platforms or tools that you want to shout out that allow you to build these agents so quickly? I know they sit on Versel, so shout out Vercel. But just anything that you point people to you to... These SDR, these GTM engineers, they're former salespeople. Are they learning to code? Are they byte coding these agents? How does that work?

Jeanne DeWitt GrosserSo our sales engineers all have CS degrees. So they were engineers in a sales capacity, so they're writing code and actually these agents, they're building directly on Versel. So you get the AI gateway that lets you call different models. You have a sandbox if you're running untrusted code, you've got workflows that let you build the process. You've got fluid compute, which lets you really efficiently use compute when you only need it. So we're just sort of building it from the ground up here. Again, it's not that hard. Now you do need to write code for that. Certainly there are a lot of vibe coding tools out there that also give you more workflow builders that are somewhere between fully WYSIWYG, almost like drag and drop and a little bit more code forward. So you've got a bunch out there along those lines. But I do think we've sort of found one of the reasons actually the GTM Eng team at Versel can build these agents so easily is because the Versel platform is making it that easy to use our framework to find infrastructure and get that agent onto into production very rapidly.

Lenny RachitskyWhat a neat, unfair advantage you all have to do this stuff.

Jeanne DeWitt GrosserYes, it is fun to... I mean, I do think this company is better than any I've seen at eating its own dog food and just everyone is constantly, we say Versel builds Versel with Versel. So you're just always looking for ways to, Hey, how can we use our product to go do what we need to do? And as a result, either understand then what a customer would want or what's missing from our product that we could go make better.

Lenny RachitskyAlong these lines, something that's already come across a lot in the way that you described this stuff is I've heard a lot about how you think about go-to-market as a product. A lot of people listening to this, as I've said, are product builders. So I think this is a really nice way of thinking about go-to-market. I'm guessing you've already talked about elements of this, but just what's a way to think about go-to-market as a product?

Jeanne DeWitt GrosserYeah, I've always, so I had this realization probably a little over a decade ago in my career. So my first job out of college was working on Gmail in 2004. So Gmail launched on April 1st, I joined on June 1st. And as I'm sure you'll remember as well, Gmail was this incredible innovation, massive JavaScript application that didn't really exist at the time. And it had this gig of storage. It was a full year before Yahoo Mail caught up and even longer before Hotmail and others did. So that was the level of technical differentiation between Gmail and the next best. And a decade later, you had cloud computing enabling folks to do stuff that you never would've been able to do previously. And so I kind of felt like, huh, software's starting to commoditize a little bit. And so when that happens, when technical differentiation kind of narrows, what are other things that will differentiate you?

And I was started thinking outside of tech, we buy a lot of things because of how we feel about them. And so I started to develop this thesis that actually the experience that you have of being sold to will increasingly actually differentiate a company and drive buying decisions if products are only different at the margin. And so if you believe that, then you really want to create a customer buying journey that feels like very unique experiences. And so we did a lot of this at Stripe and now we're looking to replicate this here. But an example of one of the things I think we did really nicely at Stripe was a lot of companies sales, the first call after you're qualified, we've decided you're worth engaging in sales process is discovery, which is basically let me ask you a lot of questions to try to under-uncover paint, figure out where buying power lies, et cetera.
And so that is kind of boring sometimes for a customer. You're basically being quizzed often on the phone. And so what we started to do at Stripe was that first session was a whiteboarding session, and we would actually get together and have you draw your architecture for payments and all the other things that were under the hood to enable you to take money and drive customer outcomes. And through that we would learn a ton about what was in your stack, what we were going to have to compete with, displace where value lied. But the customer also learned a lot themselves because in many cases they'd never drawn their architecture diagram. And so they left that meeting with an asset and a sense of like, "Wow, this is a really collaborative person who's deeply interested in helping me develop a mental model for how to think about this." And then we had other things that we would do.
So that's sort of how I think about building go-to-market-like a product is basically you need to go through from the first time you become aware that the company exists to again, that sort of five-year heavily retained wall-to-wall customer a set of experiences. And those experiences can feel transactional, flat, boring, or they can feel very human, personalized and unique. And so we try to go map those out and figure out how do you bring the product to bear, make it really human, and hopefully that creates a customer for life in the end.

Lenny RachitskyI love that whiteboarding example. Are there any other examples of what you've done to make it actually work really well in this way?

Jeanne DeWitt GrosserYeah. Another principle, we really developed this at Stripe too and I brought it to Vercel, was just the idea of adding value at any touch point regardless of whether or not that customer bought. Because even if customers don't buy, you often find that if you miss them on that buying cycle, three or four years later when they're in another buying cycle, they do come back. I was at Stripe for nine years and so I saw the number of customers that we lost and then half a decade later, here they are and they bought. So that was sort of another one. So examples of this that were doing at Vercel is there's great data on the internet that helps people understand the performance of their website and how fast your website is actually impacts SEO. And SEO impacts AEO and everybody's thinking about AEO right now. And, so one of the things we try to do when we reach out is actually give folks insight immediately into how they're performing on an absolute basis, how they're performing relative to peers. So ideally that piques your interest and you want to learn more from us, but even if it doesn't, you still have insights that you may or may not have been aware of that maybe make you contemplate whether or not you've got the optimal setup.

Lenny RachitskyAwesome. So what I'm hearing here is when you say, think of it like a product that's basically a product person thinks about the experience of their product, that every step of the journey, here's the flow, step 1, 2, 3, 4, 5, how do we make every step awesome, keep them going along that journey. And so what you think about is just from the prospect's perspective, how do we make every step of that journey awesome, continue them down that journey.

Jeanne DeWitt GrosserYeah. How do you make it be an experience rather than a transaction

Lenny RachitskyVersus just feel like sales coming at you trying to sell you stuff?

Jeanne DeWitt GrosserYeah.

Lenny RachitskyOkay. Staying along this track of staying tactical, I want to go even further there. So what are just some go-to-market tactics that you find really effective these days for people trying to just to be more successful in getting people to pay attention to their stuff, to buy their stuff?

Jeanne DeWitt GrosserI mean, one I would sort of say dovetails with where I just ended, but is what are the unique insights that you can bring to bear about your product or how that customer may be in a suboptimal state? So I do think investing in data to tease that out is one thing. I think the other thing this is straightforward but often not done enough is a lot of good companies invest in docs, good thing to do, but they stop there. And particularly if you are selling into a slightly larger company doing things like, AWS calls it well-architected guides or blueprints, a lot of customers, particularly larger ones, really want to know the best practice for how exactly to implement your product with their particular setup. A great example of this, this is from Stripe, was Stripe was excellent at marketplaces. Most, Lyft, Instacart, DoorDash, they were all on Stripe.

And so Stripe definitely knew the best way to set up payments for a marketplace because we'd seen them all. And so when you then would go and sell a marketplace and say, "Oh yeah, we've got docs, go check them out." They didn't like that, because they're like, "Hey, every marketplace runs on Stripe. I don't want to look at generic docs. I want you to tell me what's the best way to set up payments for a marketplace." And so I think that's another key thing to be doing, particularly as you move past that sort of solo developer startup founder as potentially a target audience.
And then, I don't know if this is a tactic per se, but I do think just a good reminder for founders in particular who are still in that maybe founder-led sales moment is just the value of really good discovery. I often find founders are so excited about talking about their product or you ask one question and now they've got a hook of like, oh, I can fix that for you. But excellent salespeople typically will talk well under half the time in a conversation because they're out asking questions, probing often helping a customer arrive at conclusions on their own. And so learning how to do five why's, go deep rather than immediately going into problem solving mode. If they ask a question, you respond often. If they ask a question, you should ask a question about the question and then respond. So learning to be great at that, I think differentiates people.

Lenny RachitskySo the last tip, I think there's something a lot of I bet everyone could learn is just listen more and talk less.

Jeanne DeWitt GrosserYep.

Lenny RachitskyOn that first piece of advice, this kind of sharing unique insights and how your suboptimal, is there an example you could share of how you did that? Maybe a story of just how you convinced someone you're selling Striper or Vercel like care or something you're missing. Here's how this could help you become much better.

Jeanne DeWitt GrosserSo with Vercel, sort of giving an example, but I'll make it more specific. So the performance point, you can go and look at core web Vitals, and so we can actually see the different things within their site that are fast or load correctly, et cetera, so anyone can go look that up. But what we can do is actually then help with benchmarking relative to peers. So that's been a big one that we've gone out and done. The other one that we've spent some good time on is just around helping customers understand MCP servers and when it would make sense to use one. So I think those are all the rage, but often people don't know how to contemplate them within their own product. So that was another one that we've gone pretty deep on and then related to, the first one is AEO Answer engine optimization is actually somewhat tangential to Vercel right.

So we drive performance, performance drives SEO. SEO is an input into AEO, but we have spent a ton of time sharing insights on AEO because we ourselves focus deeply on it and think we understand it better than many. And so again, as part of just building a trusted relationship, folks may go from those AMAs or that content into, okay, great, you taught me a lot and therefore I want Vercel to help me with performance. But in many cases, they actually now are just like, "This is a company that seems insightful, it seems like one I can learn from, and now I'm going to pay a little bit more attention to them." And over the fullness of time, maybe they see something that triggers them to decide, "Now is the time I want to go investigate that aspect of Vercel."

Lenny RachitskyAwesome. So what I'm hearing here in many ways, and this resonates, I had Jenna Abel on the podcast recently and it was all about sales skills and how to sell.

Jeanne DeWitt GrosserNice.

Lenny RachitskyAnd one of her tips is you don't want to be focusing on here's the pain and problem we're solving and instead focus on here's how you will be better than your competitors. Here's the big gap and alpha that you can achieve. If you use Vercel, you were missing out on speed and you're going to get screwed in AEO and all these things. Here's how you can architect your entire payments system to be top tier. Does that resonate?

Jeanne DeWitt GrosserYeah, I was told this stat. It's round numbers, so I can't imagine it's entirely accurate, but basically that customers, 80% of customers buy to avoid pain or reduce risk as opposed to the other one out of five to increase upside, which is a good thing again for startup founders to understand. So we all love to talk about the art of the possible, everything we're going to enable in the future. It's very exciting. Everyone's visionaries, but that's often really a sale that's going to resonate with another founder. And for everybody else, particularly enterprises, you're avoiding the risk of not making your revenue target next quarter, the risk of being outdone by the competition, the risk of having brand damage, et cetera. And so it's really hard actually for many startups to make that pivot because it feels off brand, but it does actually drive more buying behavior, is setting up a little bit of that concern that either I might not be well positioned or again through good question asking. I know exactly where I'm not well positioned and you can help me, that

Lenny RachitskyThat is such an important stat you shared. This has come up actually before in this podcast that buying, people are buying in large part to reduce risks, to basically not hurt themselves in their career, not hurt the company. That's a bigger factor in the buying decision than, "I have this problem I need to solve. And okay, thank you, this is solving." And the way April Dunford came in the podcast and talked about this of just like it's such a massive career bet. We are going to bring in product X and it's going to become, like Stripe, let's say, let's not talk about Versel. But let's say Stripe, we're going to adopt Stripe. That's a huge decision. If it doesn't go well, your career is hurt, your manager is going to be mad at you, it's going to set your company back. So a lot of the buying decision, as you've said is I just don't want to screw this up.

Jeanne DeWitt GrosserRight. Absolutely.

Lenny RachitskyOkay. Along the line of tactics, something that I know you're a big fan of and help people think about is segmentation.

Jeanne DeWitt GrosserYes.

Lenny RachitskyThis is something a lot of founders struggle with. They know, "Okay, I need to figure out my segmentation strategy and here where we're going after." Can you just give us a primer on segmentation, what people should know about why this is important and then how they might approach this.

Jeanne DeWitt GrosserSo segmentation is basically how do you carve up the world of companies that exist on the planet to reason about them where they buy differently? So I'll give examples from Stripe and Versel to bring this home. So a very typical company segmentation is small, medium, large. That's a rational way to do things. Small, you often have a single decision maker, medium, a small team, and large, it's complex, it's a committee, et cetera. So the buying process does change across SMB, mid-market enterprise, but if you stop there, you are likely missing. But what are the things within your offering that also change the way something gets sold? So at Stripe, there were two ways we further cut the business. Way one was, so think of segmentation as a graph. So X-Access was size, so small, medium, large, y-access was growth potential. And that was important for Stripe because it was a consumption-based business.

So if you were going to grow at 200% year-on-year, you were more valuable to Stripe than if you were going to grow at 8% year-on-year. And so we wanted to spend more time, spend more money going after the 200% growers than the 8%. So that was one that informed your strategy on who you targeted. And then for Stripe, the other thing that we cut it was business model. So are you a B2B? Are you B2C? Are you B2B2B, E.G. a platform or B2B2C, E.G. a marketplace and why is that relevant? Well, if you're B2B, you are going to need business payments. Credit card was useful for a PLG function or PLG sale, but you were going to need ACH wires, etc. And you probably had a recurring business, so you were going to want Stripe billing. If you were B2C, that's consumer.
So you're going to want consumer payments. Apple Pay is super important. If you were in the platform or the marketplace, you were going to buy our connect product. So it helped us basically then craft a more targeted and replicable sales. Vercel, sort of similar deals. So small, medium, large buying complexity. We also do the same thing on growth potential because we are similarly a consumption based business, but for us, a couple other things on the X-axis, we layer in promote, which is one of the things that is observable is traffic, site traffic on the internet. So Google publishes a Crux score, which is basically they have a bunch of data in Chrome, and so they know that Lenny's site gets a million XC amount-

Lenny RachitskyMillions.

Jeanne DeWitt Grosser... volume that Jeanne's site does. And so basically if you are a small company but you have super high traffic that's going to be more complex, Vercel is going to make more money and so we want to promote you.

So great example of this would be OpenAI. OpenAI, I forget these days how many employees it has. Let's say it's 3,000, it's probably more than that at this point, but so that's going to put it in the mid-market at most companies, but they're a top 25 traffic site on the internet. So for us, that's going to push them in our enterprise because we need to go lean in with a much more in depth sales process. And then the other thing we layer on is a workload type. So if you are an e-commerce company, that's going to be a very different sale. You actually use different language. You talk about product listing pages and product description pages, and you've got an order management system as the back end. Super different from a crypto company where you might be running soup to nuts on AWS. And so again, that helps us start to then have a really different buying content for you.

Lenny RachitskyOkay, this is awesome. So essentially what you do is you break up this universe coming back to your original story at Stripe to help you sort essentially which companies are most likely to buy your product. And what you're coming up with is these attributes that are correlated with they're likely to be great potential customers.

Jeanne DeWitt GrosserYep.

Lenny RachitskyDo you recommend using this XY axis as the approach versus something else? There's like a spreadsheet with five columns. I don't know, how do you start?

Jeanne DeWitt GrosserThere's probably something to be said for X and Y. like do you think size is going to play into most buying decisions and then these days there is a fair amount of consumption happening? So there'll be aspects of this that I think are somewhat universal. But I think basically when I came to Vercel, because new product market product offering, for me it's a new market. I had a lot to learn, but this is one of the first things I did in the first 30 days. And so basically I sat down with the gentleman Abhi who leads data science here and said, okay, what drives revenue? So what are the things that you can look at X ante about a customer to know this person's likely to pay us a hundred thousand dollars versus a million? That's probably going to be part of a segmentation framework. And then similarly, okay, what attributes would we look for to cluster where we seem to be winning repeatedly? And that was how we ultimately got at, okay, Crux rank is going to be super important because what you pay Vercel is correlated with your traffic. And then workload type was super important as well.

And for Vercel, when we did that, it was really interesting because we saw, wow, we have a lot of penetration and e-comm not that surprising actually, given that we drive highly performant sites and e-comm having a superfast performance site really matters. But at the time, if you looked at as an example, an enterprise SaaS companies, we didn't have a lot of penetration, even though you would've thought, okay, front-end cloud, very developer oriented. Of course software companies would be on us, but in enterprise, most of those companies built that SaaS offering before Vercel existed. So migrating 2 million lines of code to Vercel, that's a big lift. So it helped us really understand where are we winning, where are we not? And now as an example, within SaaS companies and enterprise, we're actually seeing a lot of interest in the AI cloud. Those are some of the earlier adopters of, "Hey, let's add AI native functionality to our existing SaaS app." And so again, it helps us figure out what to target where.

Lenny RachitskySo essentially you're doing this regression analysis on what's working and then here's the attributes that are most correlated with success. Something I always recommend when founders ask me for how do I figure out my CPE? How do I figure out where to focus, my heuristic is just think of three attributes that narrow them down. So it's like series A company that's angel-led, that's the marketplace, something like that. Does that feel like a good just rule of thumb just to start?

Jeanne DeWitt GrosserYeah, I think beyond three, that's getting pretty detailed and reasonably speaking, you're not going to cut. You have five sellers. So, what, you're going to put one seller in five different segments? So I do think three is something you can reason about. The other thing I'll say on this topic that I think is really important is a lot of times folks think segmentation is a go-to market thing. I really think it's a company thing. So when you Vercel, I actually deliver and every new hires first week, one of our company values is KYC, know your customer and I deliver the KYC section and talk through our segmentation framework how our customer base maps into those segments because it's really important as those new product managers leave the room that when they're building something, they think to themselves, okay, I'm building a new back end product. Who is this targeted at? Is it targeted at an enterprise or a startup? Basically, do I have a point of view on where I'm trying to win and why? And if you're doing that out of the gates, then it's much easier to then go speak the same language with the go to market org and figure out, okay, how are we going to take that to market in line with the other emotions that we have in play?

Lenny RachitskyOkay, this is a great segue to, there's a couple other things I want to talk about. One is something I've heard from so many people you've worked with is that you are amazing at building a go-to-market org that works really well with product and engineering. So I'll read this quote from your former colleague, Kate Jensen. She said that your superpower is building a sales org that doesn't feel like a sales org to engineers. So the question she suggested asked just what does it take to do that? What are the ingredients to building a sales org that engineers and product teams really like working with?

Jeanne DeWitt GrosserThe litmus test I have always given my sales team is if you are an account executive in my org and I put you in front of 10 engineers at our company, it should take them 10 minutes to figure out you aren't a product manager. And what I'm trying to get across is you need to have incredible product depth. And the reason for that is twofold. One, it gives you credibility with the product and engineering org. And two, I also believe that the best go-to-market orgs on the planet are equal parts revenue driving and R&D and D. And the reason I emphasize the latter is if you think about a product management organization, you may have a UXR team out doing research, product managers certainly should be out talking to customers. Well, if I have a 20-person sales team, think of the number of customers that we talk to in a week. And so if we can do an excellent job of translating all of that feedback into signal and then feeding that into the road map, we can be actually an extension of the product management org. But that takes being really good at discerning signal from noise, understanding when something is an objection that should be overcome versus an opportunity in the market. So I think those things have helped.

Lenny RachitskyI just love this as a product manager, maybe form a product manager. I don't know what the hell I am these days. I just love the idea of the salesperson. Like you not knowing the difference between a product manager and a salesperson. The most classic challenge is sales orgs ask for all these features and PMs are constantly having to push back and think about does this fit into everything. So it feels like that's a big part of this is to understand that deeply.

Jeanne DeWitt GrosserYeah, you want a sales org that can think like a general manager, so that's not just trying to get deals done but is trying to help build a business. And so again, knows when to say no, knows when to do objection handle versus knows, Hey, I've actually heard this on the last three calls and I do think this would be a really big unlock that would make us more competitive, would be something that new that nobody's doing. So I think that takes looking for a profile that both has sales skills but also is going to think with that product mindset.

Lenny RachitskyI love that. Okay, so another quote from Claire Hughes Johnson, former podcast guest, amazing sales leader, worked with you at Stripe. She said something along these lines, but a little different. Jeanne is probably the best go-to-market person at connecting with product and engineering, deeply understanding the product and providing the most valuable input to her counterparts of any I've ever seen. It sounds like just another ingredient here is just sales feeling like a real partner to product engineering actually, not just being like, "Hey, do these things for me, but actually feeling like a partner."

Jeanne DeWitt GrosserUltimately company strategy is basically product strategy meets go-to market strategy. And so I spend guess as a go-to market leader, I'm constantly trying to figure out how do I make more money more efficiently? And you typically do that by having a winning product in the market that is well commercialized. And so that means that I really lean into thinking about product strategy and thinking about pricing strategy because if those two things are optimal, you're going to win more often and there'll be less friction in it. And so that's sort of where got to put as a revenue leader, like a GM hat on and not just think, how do I sell? But actually how do I enable the insights I'm getting from talking to customers constantly to have the company strategy be more effective?

Lenny RachitskySpeaking of product, going in a slightly different direction, PLG product-led growth, it felt like it was very hot for a while where everyone's like, "You got to go PLG, that's the only way to win. It's impossible to do sales. The future is PLG." It feels like that's gone away. And in large part, obviously still companies grow through PLG and work through PLG. What's just kind of your thoughts on PLG and when does it make sense for a company these days to actually think this is how they'll grow for a while?

Jeanne DeWitt GrosserPLG makes sense for a lot of companies at the outset, unless you are very explicitly building a product for enterprise. So Sierra as an example, right? They are very clearly going after Global 2000 or something close to that. PLG is not going to be overly useful to them because they are trying to win eight-figure deals from day one. But for a lot of products, folks are targeting a startup audience at the outset and then they're adding more functionality so that they can ultimately continue to scale up market. So I think PLG is still super relevant. It's a major driver of Vercels growth. It was a big driver of Stripe's growth. The thing that folks get wrong is it does typically have a ceiling. So people are generally not going to give you $1 million via self-serve flow. So at some point if you want to sustain growth rates, you're going to have to have your deal sizes get bigger and bigger. And where I think folks get stuck is waiting too long on PLG because it does take a while to build a replicable sales process and a sales process, which often you're getting fed by inbound at the beginning and then you got to add outbound. It takes a while actually to turn outbound into a predictable engine. So I think where you see companies hit walls is just when they don't add the sales portion of it soon enough.

Lenny RachitskySo essentially every company ends up having to build a sales org, some start product-led and then at sales, some just start sales and have it from the beginning.

Jeanne DeWitt GrosserYeah, I would agree. There are probably some good examples of large vertical SaaS platforms that are SMB, but even they wind up with Velocity sales team. So yeah, I don't know that I can think of a 100 billion company that's PLG-only.

Lenny RachitskyYeah, it just feels like you're leaving money on the table even if you are growing really fast. I know Atlassian was a long-time PLG company but eventually succumbed. I don't know if that's the right way to put it. Okay. You mentioned pricing. I know you have strong opinions on pricing and pricing strategy. What's just a couple of tips you might share with someone thinking about how to price their product?

Jeanne DeWitt GrosserYeah, this is kind of on the theme, but I think the first thing is you got to think about pricing like a product. So it's another one where it actually really matters how you choose to price a product. Do you really understand where customers are going to drive value? Do you really understand where you incur costs? And are you doing a smart job of aligning those things? You've got lots of examples of companies grossly underpricing, you're sort of afraid to charge for the value that you actually provide. I think there are a lot of examples where people default to including a freemium strategy without that actually being a strategy. A good example at Stripe, we launched Stripe Billings years ago. It had a freemium strategy because that's what you do. And then we sort of looked at it and we're like, "actually integrating straight billing takes a little bit of work.So if you do that, you're probably going to stay."

And so we killed that, killed the free trial to zero downside. So that's another one. At Vercel, we've been going through that transition where we're a consumption-based business model ultimately, but at the outset we basically kind of bundled that into what looked like a SaaS-like price and as we've added a lot more functionality that wasn't working anymore. And so we did an unbundling and right now actually we did a pretty substantial pricing change in August where we have an enterprise at a pro-skew. And if you looked at the enterprise skew, it's called Enterprise for a reason, enter, it's meant to be sold to an enterprise. And actually about half of the folks on the enterprise skew were startups, which suggests that there's stuff in the enterprise skew that a startup really wants. So we kicked a lot of that stuff out of the enterprise skew and made it so you could buy it self-serve online and what do you know, people are.
So now that's really driven a lot of growth in our PLG funnel, which is awesome for startups because it's super efficient. They can just buy things, they want that. It's awesome for us because you don't have to have a human intermediate that. So getting all of these knobs really tuned is a key to both a great customer experience and optimal revenue outcomes.

Lenny RachitskyMaybe just one more question before we get to a very exciting lightning round. It's going to be a combo question. I hear you have a hot take on sales comp, how to comp salespeople that's different from other people and also who to hire when you're hiring folks in sales. Can you just talk about your takes there?

Jeanne DeWitt GrosserI struggle with sales comp because it's all about pay for performance, which I'm obviously a fan of, but it makes your organization less flexible because you basically have to decide 12 months in advance, these are things I value and particularly in this moment that could be different. As a great example of this, when we wrote the sales plans for this year at Vercel, the AI cloud did not exist. We were selling our front-end cloud and we were selling VZero and introduced the AI cloud halfway through the year. Now we had all sorts of good ways to still incentivize that, but I think you want to be able to be innovative and pivot and when you have a well-designed sales plan or a very structured sales plan, that can be challenging.

So that's a little bit of my hot take is just I'm trying to figure out how do you have the upside of sales of motivates people. It's a quantitative function, which is great, but also the flexibility to change your mind because I think a lot of companies right now are having a hard time doing annual planning. So that's one. On profiles, I have always valued just sort of a diversified portfolio. So I strongly believe that sales is a skill and so you want salespeople with actual sales experience in your organization, but I think there's value in pairing them with more nontraditional backgrounds, in particular consulting or banking background. Those folks are really good at more quantitative and analytical aspects of sales. So getting into that consultative part, which I think we talked about at the outset. And so I find that when you mix these together, the sort of consultant banker profile realizes, "Oh wait a minute, sales is a skill and I didn't really have it." And so they go learn from your account executives with that background and then your AEs learn more about, okay, how do I think about a P&L? How can I talk to a CFO? How do I present a TCO analysis more effectively? And so just creates a much richer learning environment where people are bouncing ideas off each other.

Lenny RachitskyThat is awesome. I love that strategy. Okay, final question. Just is there anything else you wanted to share? Anything else you want to leave listeners with before we get to our very exciting lightning round?

Jeanne DeWitt GrosserOh man. I feel like we've been very thorough.

Lenny RachitskyAll right, thanks So too.

Jeanne DeWitt GrosserYeah, you stumped me on that one.

Lenny RachitskyOkay. That's the goal. With that Jean, we've reached our very exciting lightning round. I'm going to make it very quick. I know you got to run. I'm going to ask you just two questions.

Jeanne DeWitt GrosserOkay.

Lenny RachitskyOne is I'm going to skip to your life motto. Do you have a favorite life motto that you often come back to find useful in worker and life?

Jeanne DeWitt GrosserI do. I actually have found that I'm known for saying a handful of things that I didn't necessarily realize it, but when you leave an organization, people tend to tell you what stuck with them. But there is one that I think I am known for saying growing up, my mom always said to me, when the going gets tough, the tough get going. And in sales, you're always going to have a quarter when you're not on pace. And so that's one that I feel like I pull on, not infrequently because in my view, there's another version of this, my mom also always says was where there's a will, there's a way. So I think you can always choose to find a path forward even when that's not super clear.

Lenny RachitskyI love these. Okay, last question. I read that you were a very competitive diver in college early on. I'm just curious if there's something you learned from that experience that brought with you that helps you be as successful as you've become?

Jeanne DeWitt GrosserWell, I mean, first of all, I should say I was generally coming in third place out of three on my team.

Lenny RachitskyThird place, that's not bad.

Jeanne DeWitt GrosserI managed to do it in college, but that was the extent of that career. So diving is a precision sport and it is a repetitive sport. And it is also a sport where when you land flat on your back, and literally as you are swimming to the side of the pool, welts are forming on it, you always 100% of the time will be forced to immediately get back on the diving board and do that exact same dive again. And so I think that has a lot of stuff that's transferable to work and to sales. So for me, I just have an obsession with excellence and within sales. sales is about replicability. How do you drive predictable outcomes, how excellent are you at your ability to forecast? And so I think I bring that to bear within sales a lot. And then similarly, you get a lot of nos in sales. So another phrase that a sales guru said to me once or in a training was yeses are great, nos are great, maybes will kill you. And so how do you get really comfortable that no is a great thing and that just gave you data and now you can go do something with it.

Lenny RachitskyThis is a really inspiring and empowering way to end the conversation. Jean, thank you so much for being here.

Jeanne DeWitt GrosserThanks so much for having me, Lenny. It was a lot of fun.

Lenny RachitskyBye, everyone.

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

Lenny Rachitsky最近来找我要 go-to-market 帮助的人特别多。

Jeanne DeWitt GrosserAI 让这件事进一步升级了，因为现在往往有 10 个玩家在追同一个市场机会。你到底能不能把产品顺利带到市场、并真正和竞争对手拉开差距，这件事的战略重要性比以前高得多。

Lenny Rachitsky我前阵子请 Jenna Abel 上播客，她有个建议我印象很深。她说不要总盯着“我们解决什么痛点”，而要更多去讲“你会比竞争对手强在哪里”。

Jeanne DeWitt Grosser大概 80% 的客户买东西，是为了避痛、降风险，而不是为了追求更大上行。这个点创业者特别需要理解。我们都爱讲“未来能做到什么”“可能性有多大”，这类话题确实很让人兴奋，但很多时候，最吃这套叙事的是另一个创始人。对大多数客户，尤其企业客户来说，他们更在意的是：别让我下个季度完不成营收目标。

Lenny Rachitsky我还经常听人说，你会把 go-to-market 当成一个产品来设计。

Jeanne DeWitt Grosser很多时候，我们买东西不是因为参数，而是因为感受。以后如果产品之间只剩边际差异，那“你被销售的那段体验”本身，就会越来越成为一家公司的差异化来源，甚至直接影响购买决策。所以你真正想打造的，是一条让客户觉得“这个购买过程很不一样”的旅程。

Lenny Rachitsky还有很多和你合作过的人都说，你最强的地方，是能搭出一支“在工程师眼里不像销售团队的销售团队”。

Jeanne DeWitt Grosser我一直给销售团队一个非常简单的标准：如果你是我团队里的 account executive，我把你扔到公司 10 个工程师面前，他们至少要过 10 分钟才意识到“哦，你原来不是产品经理”。

Lenny Rachitsky今天的嘉宾是 Jeanne Grosser。她曾在 Stripe 从零搭建早期销售团队；现在她是 Vercel 的 COO，负责 marketing、sales、customer success、revenue ops 和 field engineering。Jeanne 在多家独角兽公司都搭出过世界级的 GTM 团队，也给很多公司提供过这方面的建议。今天我们会深聊：什么叫世界级 GTM、所谓 go-to-market 到底包括什么、go-to-market engineer 为什么会成为一个新角色，以及她的团队为什么已经靠这个角色把效率拉高了 10 倍。我们还会聊很多非常具体的打法，包括分层、如何把 GTM 当产品来设计、她最喜欢的 GTM 工具，以及她对 PLG、销售提成和销售招聘的看法。如果你想系统补上最新的 GTM 思路，这期会很适合你。

Jeanne，非常感谢你来，欢迎来到播客。

Jeanne DeWitt Grosser谢谢邀请，Lenny。

Lenny Rachitsky我希望这期聊完之后，它能变成这样一个东西：以后谁来问“我想把 go-to-market 做得更好，该怎么办”，我们就直接把这期甩给他，而不是还得花大价钱去请人做顾问。那我们先从最基础的问题开始。大家一听到 `go-to-market`，到底是在说什么？它具体包含哪些东西？

Jeanne DeWitt Grosser我觉得这个问题有两个答案。

大多数人第一反应，往往会把它理解成推动收入的那一截“枪尖”，也就是 marketing 和 sales。
但对我来说，凡是会碰到客户、或者会直接帮公司赚到钱的职能，我都算进 go-to-market。实际上，我在 Vercel 负责的范围也就是这些：marketing、sales、所有偏技术型的售前角色，比如 sales engineer，或者偏售后技术架构的角色；再加上 customer success、support、partnerships。
我之所以这么定义，是因为我整个职业生涯里都在看到一个问题：这些职能常常像一个“只部分重叠的维恩图”。marketing 在追一套东西，sales 也在追，但不完全一样；support 也有它那套逻辑，也不完全重合。比如最典型的，就是分层框架可能稍微有点不一样。
所以我认为接下来你会越来越需要的是：把它们变成一个真正打通的生命周期。
尤其是在当下这个时点，我觉得 go-to-market 里的很多职能会被重新定义。我们前几年其实经历了一波 GTM 的“超级专业化”。怎么算都能数出十几种不同角色。我自己的判断是，其中相当一部分角色会开始重新收缩、合并。
如果你用更整体的眼光来看 go-to-market，就会回到最本质的问题：从一个潜在客户第一次知道你，到他 5 年后依然高 LTV、在你的平台上全链路深度使用，中间到底有哪些 jobs to be done？
你需要把这整条链路画出来，再像设计产品一样去编排它。

Lenny Rachitsky太好了。我们后面会沿着这整个 GTM 生命周期往下拆。不过如果先给大多数公司、尤其是早期公司一个简单版本，那大家说 go-to-market 时，基本上大多还是在说 sales，然后 marketing 可能占一部分；等公司再成熟一点、长大一点，customer success、tech sales 这些角色才会逐渐进来。可以这么理解吗？

Jeanne DeWitt Grosser对，大多数公司的起点大概是这样。很多公司一开始会先补 sales；但也有很多公司因为是 PLG 起步，所以反而一开始更像是先从 marketing 开始，等到需要 sales-assisted、再到 sales-led 的时候，才把销售层层叠上去。

所以这件事也得看你的产品是什么、你最初瞄准的市场是谁。有时它主要指 marketing，有时主要指 sales，有时则是两者的组合。

Lenny Rachitsky明白了。换句话说，这个词本身其实已经说明了一切：怎么把你的产品带到市场，让别人知道、开始用、并最终留下来。

Jeanne DeWitt Grosser对，完全是这样。

Lenny Rachitsky那过去几年里，go-to-market 这个世界到底发生了什么最大变化？你在 Google、Stripe、现在在 Vercel 都做过这件事。这个领域最本质的技能和方法，哪里变得最不一样了？

Jeanne DeWitt Grosser变化其实有好几层。

最早从消费型商业模式开始流行的时候，你就已经能看到 go-to-market 越来越偏向“咨询式”。因为第一次成交往往只是整段关系的起点，而且通常只占未来总价值里非常小的一部分。所以你必须从原来那种偏交易型的销售，转向更深地理解客户到底想做什么，再把这些目标和你的产品能力对齐。
而到了 AI 时代，这件事被进一步放大了。因为现在大家都知道“我得变”，但很多人并不确定自己到底该变成什么样，不管是面向客户的产品，还是内部的效率系统和工作流。
所以你现在会看到很多 GTM 团队，越来越像在做“咨询顾问”这件事：去讲可行性边界、讲最佳实践、帮客户把事情想明白。
也正因为这样，一个特别明显的趋势是：forward-deployed engineering 变多了。某种意义上它有点像 professional services 的重新包装，但又不完全是。它更像是：我真正进到你的环境里，和你并肩工作，更深入地理解你想达成什么，然后帮助你把技术真的落地，同时也在这个过程中反过来学很多东西。

Jeanne DeWitt Grosser很多时候，这么做不只是为了帮客户成功，你还会把这些一线信息重新带回产品和工程团队，去判断：哪些能力其实是通用的、值得直接做进产品里，哪些则更适合长期保留为服务的一部分。

所以我觉得，过去几年最大的变化之一，就是 GTM 团队真的更深地嵌进客户环境里了。
另一个非常明显的变化，当然就是：AI 正在被真正用进销售流程本身。
过去 18 到 24 个月里，一个很有代表性的现象，就是 go-to-market engineer 这个角色开始冒出来了。不同人定义会略有不同，但本质上有两个层面。第一，是把更强的技术能力真正带进 GTM，让工具链、数据使用方式这些东西变得更强。第二，是把 AI 逐步引入进来，重新设计你的工作流，让你既能提供更个性化的客户体验，又能在规模上跑得动。

Lenny Rachitsky太棒了。那我们就顺着这个 go-to-market engineer 往下聊。以前的做法是什么样？现在这些工程师到底在公司里干什么？

Jeanne DeWitt Grosser我讲个故事会更直观。

我当年在 Stripe 时，准备启动 outbound SDR 这个职能，也就是主动拓客。Stripe 一贯是很精简地运营。那时候公司有一句原则，叫 `efficiency is leverage`。所以如果你看当时我带的销售组织，换成别的公司，大概率会给我配 30 个 SDR，但我最后只拿到了 4 个。
那就意味着，我根本不可能按传统 SDR 的打法去做，还想把事做成。
于是我们就开始想：那还有什么方式？答案是，极端数据驱动。
我们当时做了一个项目，叫 `Project Rosaland`。Rosalind Franklin 是最早做 DNA 结构映射的科学家。这个项目本质上就是一个“公司宇宙”。你可以把它理解成一个巨大的数据库，每一行是一家地球上的公司，每一列则是这家公司身上一个能帮助你更精准销售的属性。
比如在 Stripe，一个非常关键的属性是：它是不是 marketplace。因为如果是 marketplace，你就应该卖 Stripe Connect，而不是普通支付。
所以我们的目标其实是：能不能做出一个“Mad Libs 式”的销售系统？我预先写一个邮件模板，但其中 80% 都是可填空的，会根据客户属性动态替换。比如如果它属于某个行业、某种商业模式，那就调对应的案例、价值主张，发给对应 persona，而不是另一类人。
我们在 2017 年就在做这件事。但当时非常难，最后也没有真正跑通。我们和数据科学团队深度合作过，但 false positive rate 始终降不下来，一直差口气。
而我们现在在 Vercel 几乎就在重做同一件事，但这次是真的能用了，因为 AI 已经可以参与进来。
现在最大的不同是：我依然有 data scientist，就像 2017 年一样；但我还多了一个 go-to-market engineer。以前我只有系统侧的人帮我配置 outreach、Salesforce 这类工具，现在 GTM engineer 会真正和我一起去构建 agent。
我们会先拆：如果这是一个人类在做，他原本的 workflow 会是什么样？然后再把这套流程编码进去。比如用 Vercel workflows 把它写成一部分确定性的逻辑，加上一部分 agent 去完成更开放式的判断，让它尽可能复现人类本来会做的那种“填空式销售动作”。

Lenny Rachitsky我太喜欢这个项目的野心了。这还是大概八年前的事情？

Jeanne DeWitt Grosser对。

Lenny Rachitsky真的很猛。去画出整个公司宇宙，再决定怎么卖给它们。而且现在回头看，没有 AI 你居然还试图做这件事，真的很不可思议。现在反而一想就能明白它为什么能成立了。

Jeanne DeWitt Grosser有趣的是，后来很多当时和我一起做这件事的人，现在都在不同地方以新的方式把它继续做下去。

举个例子，当时和我一起做这件事的 Ben Salzman，后来去了 ZoomInfo，最近又自己出来创业，做的就是把“公司宇宙”这个概念产品化，再把 AI 叠上去。他甚至在想，未来 AI 也许会发展到一个程度，根本不需要传统 outbound prospecting 了，因为系统会自动完成“公司和产品之间的匹配”。
所以你现在回头看会觉得很有意思：2017 年那批在折腾这些东西的人，如今有人去了 OpenAI，有人去了 Anthropic，也有人继续在做 GTM engineering，还有人像 Ben 一样直接做出一家原生 AI 的 GTM 公司。而我现在在 Vercel，也在试着把这条路重新走一遍。

Lenny Rachitsky这里特别酷的一点是，这真的是一个正在浮现的新角色、新技能。很多人可能都还没意识到这已经开始发生了。

所以现在我听到的一个很典型的例子是：这个角色会去自动化 outbound 邮件、本质上就是自动化外呼。它会写 workflow、写 agent，去判断该追哪家公司、该怎么发消息。最后出来的，会是那种为 конкретный 目标客户专门写的邮件吗？

Jeanne DeWitt Grosser那只是其中一种应用，而且它的范围其实远比这个更大。

从定义上讲，GTM engineer 最终会去遍历 go-to-market 每个职能里所有的工作流，把这些工作流拆开，然后判断：哪些任务 AI 比人更适合做，再把它们逐步变成 agent。
我们现在是从 inbound 开始，接着往 outbound 走，因为 inbound 那套流程最“可读”。我说的可读，是指它比较容易被写下来，也比较可复制，确定性更高，所以 AI 比较有机会把它做好。我们会先把 agent 搭出来，然后保留 human in the loop。
比如在 inbound 这个场景里，第一步你要判断这个 lead 值不值得跟进；第二步你要决定该怎么回复。我们就先让 agent 做这两个判断。
它会去做深入研究，调用我们数据库里的很多信息，再起草一封回复。但最后仍然是由人去 review、再点发送。
以前我们有 10 个 SDR 在跑这个 inbound 流程；现在基本只需要 1 个人来做 agent 的 QA，剩下 9 个我们已经调去做 outbound 了，也就是把他们推到了更高价值的一层。
以后我们当然有可能会走到一个阶段：人类 reviewer 的通过率已经高到足够放心，我们就能判断这些回复已经足够符合品牌调性、足够精准。只是现在，我们还在继续训练 agent，也会把那些被我们拒绝、修改的地方继续喂回去。

Lenny Rachitsky我特别喜欢这点。这是一个 AI 在高 ROI 场景里真正发挥杠杆的例子。那些原本你得雇几十个 SDR 才能完成的工作，现在可以用很少的人做更多，特别有说服力。

不过很多人一听到这里，第一反应会是：“完了，以后我是不是会收到更多垃圾销售邮件？一眼就看出是 AI 写的那种。”你们在这方面学到了什么？怎么才能把它做成真正有效、能转化、而不是只会惹人烦的东西？

Jeanne DeWitt Grosser我们的所有流程现在都保留 human in the loop。

而且在开始的时候，我们会让一个 GTM engineer 先去 shadow 这个职能里最强的那个人。比如你去跟一个最优秀的 SDR 一整天，你会看到：他同时开着七八个标签页，在 LinkedIn 上查人、看公司资料、用 ChatGPT 帮忙补信息、再去另一个数据库抓属性。你把这些动作全看清楚，就能还原出最初的 workflow。
然后我们让 agent 先自己做判断。还是拿 inbound 举例，它需要判断这个 lead 是否合格，以及该说什么。我们就先让 agent 完成这两步。
接着它会去做更深层的研究，从我们的数据库里拉很多信息，再写出回复。但最终还是由人去审，再点击发送。
对我们来说，原来有 10 个 SDR 在跑这个 inbound workflow，现在 1 个人基本上就够了，这个人的角色更像是 agent manager。那 9 个人就被我们重新部署到了 outbound，那是更高杠杆的位置。
而且我们不是盲目切人的。整个过程中，我们一直在盯传统 SDR 该被考核的那些 KPI：比如 lead 到 opportunity 的转化率、转化需要多少次触达、整体响应时长等等。
最后我们看到的结果是：lead-to-opportunity 转化率基本持平。也就是说，agent 已经能做到和人一样好。
但它把转化所需的触达次数压缩了，因为它响应得更快。现实里，lead 往往会在队列里堆着，或者半夜来了也没人理，但 agent 不会等。所以当这些指标都达到我们能接受的程度时，我们就知道：可以把 9 个人从 inbound 挪去做 outbound 了。

Jeanne DeWitt Grosser对，我觉得差不多是这个量级。作为创始人，你还是得长期贴着客户，做到一定规模，也做到你刚才说的那个关键词：有一定“可重复性”。

很多创始人容易忽略的一点是：创始人通常本来就是很强的销售。你能说服 VC、天使把钱投给你，说明你本来就很会让人相信你。但如果你做到 100 万美元 ARR 时，手上的客户彼此几乎毫无共性，那你其实还停留在一种 evangelist sale、也就是非常 founder-led 的销售阶段。
相反，如果你已经能说出一套明确的 ICP，比如：“我们的产品最适合员工少于 100 人、正在做 SaaS 的创业公司。”那你大概率就已经到了可以把销售这件事交出去的阶段。
但创始人还要记住，所谓“交出去”，是真的要交。你得把自己原来是怎么做的说清楚：你的内容是什么？你会问哪些 discovery 问题？你怎么处理 objection？这样新进来的人才能真正接住。
当然，也不是说你可以彻底撒手。你仍然要继续贴着客户，因为在公司继续扩张的过程中，你还有很多 R&D 要做：产品下一步会在哪些地方继续共振？扩张时会卡在哪里？这些都还是创始人必须持续感知的。

Lenny Rachitsky那再把 go-to-market engineer 这个话题收个口。理想中的 GTM engineer，尤其是你第一个 GTM engineer，应该是什么画像？

Jeanne DeWitt Grosser我们现在观察下来，最有效的画像是：这个人本身就有 go-to-market 经验。

在 Vercel，我们最早的三位 GTM engineer，其实原来都是 sales engineer。Vercel 招的 sales engineer 本来就很技术型，他们之前全都做过前端开发，后来才转进销售。所以我们干脆直接跟他们说：“恭喜，你们现在就是 GTM Eng 团队的 founding members 了。”
这类人好用的原因在于：他们懂什么叫好的 GTM，也懂一个流程长什么样。
这里有个很有意思的小例子。负责 GTM Eng 的同事跟我一起在看 lead agent 的 QA 结果时，我看着 agent 发出去的一些回复，心里会想：“这个如果是我，我不会这么写。”原因很简单，我有 20 年销售经验，而我们这个 lead agent 最初是按“团队里最好的那个人”去建模的，可那个“最好的人”其实只有 2 年销售经验。
所以你会发现，理解销售这件事的“术”和“道”都很重要。你要么自己做过，因此知道什么是 best practice；要么就真的愿意钻进去学，去读很多销售书、理解里面的结构，再把这些东西装进 agent 的开发过程里。

Lenny Rachitsky这点太有意思了。也就是说，理想起点更像是从销售侧长出来，而不是从纯工程侧长出来。我感觉这对销售人来说也是个很酷的新机会，可以借这个角色离工程更近。

Jeanne DeWitt Grosser对，我们自己也玩得很开心。

尤其在 Vercel，我们基本上就是 customer zero。我们现在所有和 agent 有关的东西，都是直接建在 Vercel 的 AI cloud 上。一个 agent 背后通常要走很多步，所以我们会用 Vercel 的 workflow SDK 和 workflow 产品去搭整个流程，用 AI gateway 去调用不同模型，做深度研究或者其他 enrichment。
所以对我们来说，这件事特别妙：我们一边在用，一边也在“折腾”工程团队正在做的那些能力，相当于先在真实内部场景里做一个特别挑剔的客户，再把它推给外部客户。

Lenny Rachitsky真是个很适合活着的时代。光听你描述，就能感觉到你们玩得很开心。

（Stripe 赞助口播已压缩省略）

Jeanne DeWitt Grosser这个问题我会给一个有点特别的答案。

我先讲一个工具。它不一定算“最新最潮”的 state-of-the-art，我不是在贬义地说它，只是它已经存在一段时间了，很多人都在用。但我确实觉得，过去一年 Gong 变得有意思太多了。
另外，等下我还会讲第二个点：现在 build 还是 buy，这个判断逻辑正在变化。
先说 Gong。Gong 现在特别强的一点，是你已经可以在它上面跑 agent 了。我们会把所有 Gong transcript 都灌进一个叫 `deal-bott` 的 agent 里，它能做很多事。我们最开始让它做的是 lost opportunity review。
当时我们刚结束 Q2，手上有一张按 deal size 排序的“本季度最大丢单”清单。我们把它丢给这个 agent 去分析，结果特别有意思。
那一季度最大的一个丢单，account executive 自己给出的结论是：输在价格。
但当 agent 跑完所有 Slack 互动、邮件、Gong 通话之后，给出的结论却是：你真正输掉这单，不是因为价格，而是因为你从头到尾没有真正触达到 economic buyer。以及，当你和对方聊 ROI、聊 total cost of ownership 的时候，从对方反应里能看出来，他们其实并没有真正买账你的那套测算。
也就是说，这单真正输掉的原因，是我们没有把价值讲透。
这件事让我自己也反思：Vercel 的价值其实非常容易量化，这也是我很喜欢卖这个产品的原因之一。但我们还没有把这套价值量化方法，充分 codify 给 GTM 团队。
所以这次分析就非常有帮助。现在我们已经会把所有 lost opportunities 都跑一遍，比过去更准确地归因：我们到底是怎么输的。
然后这些发现要么会回流给工程团队，要么回到 marketing / sales leadership 这里，帮助我们判断：到底是销售流程哪里出了问题。
但后来我们想，老盯着“输了什么”也挺没劲，不如再往前走一步。于是我们从 `lost bot` 进化成了 `deal-bott`。
现在这个 `deal-bott` 是实时运行的，而且我们会把它的洞察直接喂进 Slack。Vercel 内部是 Slack 的重度用户，我们几乎给每一个客户都开单独频道，不管是还在推进中的机会，还是已经成交的客户。
于是现在 agent 会直接在那个 Slack 频道里提醒你：
“你们这个 deal 已经推进到这一步了，但你还没有接触到经济决策人，最好留意一下。”
或者：
“你刚和经济决策人开完会，听起来效果一般。下面这几个方向可能值得你 follow-up。”
还有一个特别有意思的用法。现在这个时代的迭代速度，是我 20 多年技术职业生涯里从没见过的。对 GTM 团队来说，这其实很难，因为如果你每隔一天就上线一个新东西，团队根本不容易及时被 enable 到位。
于是这个 bot 现在还开始帮我们做另一件事：每次产品发布之后，我们会先尽量去 enable 团队，然后再让 agent 跑所有通话、互动记录，看看我们到底哪里 objection handling 做得不好，哪里卡住了。
到了周末，我们就可以开个 huddle，集中看：这个星期 agent 认为我们在哪些地方卖得不够好？
然后像工程团队那样去跑 sprint。因为这些问题本质上就像 bug，一旦发现，就不该继续留着。
于是下周我们会去补 objection handling guide，会补 discovery guide，会改 demo，诸如此类。现在这套东西还比较早期，但这就是我们眼下在 GTM 团队里真正往前推进的方向。

Lenny RachitskyJeanne，你真的一次又一次把我听傻了。听起来这太好玩了，我脑子里的感觉就是：你们会赢。而且这里最厉害的一点是，这个 AI agent 看到了人根本没看到的东西。你居然会得到一个完全不同的结论，这太重要了。这几乎就是大家一直在说的 AI promise：它会看到那些我们没想到、甚至根本看不到的东西。

Jeanne DeWitt Grosser没错。我们最近还有个特别有意思的案例。

Vercel 现在有 AI cloud，客户既会拿它给自己的面向用户产品加 AI-native 功能，也会用它来做内部应用，提升效率或者结果。我们最近就在和一家非常大的航空公司聊。
航空公司当然每天会收到海量支持请求。所以最直接的想法就是：用 AI 去回答这些支持问题，把 support 成本降下来。这很自然。
但更有意思的是，他们一位 C-level 高管说：我们其实还会把每一通支持电话都转成文字。我真正想知道的是，客户为什么打来？以及，我怎么才能让下周打电话的人更少一点？
这时候 AI 的价值就非常明显了。它可以快速扫完所有这些内容，比过去靠人在 CRM 里手工给每通电话挑一个状态标签快得多，也更有机会真正总结出：这周大家到底是为什么打电话进来？我们能做什么，让下周这种情况少一点？

Lenny Rachitsky我猜很多人听到这里已经在想：“我也想要一个这种 `deal-bott`、`lost bot`。”这些都是你们自己内部搭的吗？

Jeanne DeWitt Grosser对。

Lenny Rachitsky那你们有没有总结出一些经验？比如，想做一个真正好用的销售 bot，有什么关键心得？

Jeanne DeWitt Grosser有，这其实正好就是我刚才还没讲完的第二部分。

Lenny Rachitsky太好了。

Jeanne DeWitt Grosser也就是 `build versus buy` 的判断。

我们现在一个很明确的体感是：这些 agent 没你想的那么难做，也没你想的那么贵。
比如我刚才说的 lead agent，是一个人、花了大概三分之一的工作时间，六周做出来的。`deal-bott` 更夸张，最早的 `lost bot` 版本，基本上两天就做出来了。40 小时左右，它就已经能跑起来。后面我们当然还在继续打磨。
还有一个很夸张的事实是：对 Vercel 来说，这些 agent 的运行成本低得离谱。
那个 lead agent 是完整跑在 Vercel 上的，全年运行成本大概只有 1000 美元。但你还记得吗？我们原本有 10 个 SDR，光工资成本就远超 100 万美元。
现在我把它压到 1 个人，后面再配一个全年 1000 美元的 lead agent。总成本基本上是 90% 以上的下降。
现在外面当然有很多 agent 软件。但我们学到的一件事是：因为这个领域还很早，真正决定 agent 威力的，往往恰恰是你自己那套很具体、很“土味但独特”的上下文、内容和 workflow。
所以我越来越觉得，自己去试着搭内部 agent 很有价值。未来当然也可能会出现更好的一体化 agent 平台；也可能 CIO 的角色会从“软件采购者”慢慢变成“软件构建者”，然后你公司内部会有一个 AI 平台，跑着上千个 agent。
我现在还不敢说最终一定是哪条路。但我非常确定的一点是：值得你先自己试一试。因为你很可能会发现，它比你想的容易，而且回报来得比你想的快。

Lenny Rachitsky所以你的意思是，真正的 alpha 很大程度上其实还不在“现成即插即用的工具”里，而是在自己搭。

Jeanne DeWitt Grosser部分是这样。

还有一个现实问题是，现在工具实在太多了。结果往往就会变成：20 个 jobs to be done，要买 20 个工具，而不是有一个整合平台全包。
我最近和客户聊天时，这几乎成了一个高频痛点：他们部署 AI 最大的问题，反而是 procurement 流程根本过不去。因为一旦公司有了 AI mandate，某种程度上就像拿到了一张“空白支票”。
我最近还听到一个说法，把 ARR 戏称成 `ERR`，也就是 `experimental run rate revenue`。意思是，大家都在说：“这个东西我们先买一年试试看，明年再决定留不留。”
可现实就是，你得为 20 个不同的东西做采购。大多数产品都还很早，所以解决的问题也都很窄。这个状态以后当然会变。
但在现在，我确实觉得你应该想清楚：哪些 workflow 是你内部特别独特、特别具体的？这种场景就很值得自己造一个 agent。至于那些更通用的问题，再去买 off-the-shelf 的工具，可能更合适。

Jeanne DeWitt Grosser我们团队里的 sales engineer 基本都有计算机背景，本质上就是“做销售的工程师”。所以他们会自己写代码，而这些 agent 也确实是直接搭在 Vercel 上的。

你可以用 AI gateway 去调不同模型；如果要跑不受信任的代码，也有 sandbox；workflow 可以帮你把流程编排起来；fluid compute 则让你只在需要时才高效使用算力。我们基本就是从底层一层层自己搭上来。
所以我还是那句话，这件事没有大家想得那么难。当然，你确实得会写一点代码。现在外面也有不少所谓的 vibe coding 工具，会给你提供更偏工作流搭建的界面，介于完全可视化的拖拽和更偏代码的方式之间，这类工具其实已经很多了。
但我确实觉得，Vercel 的 GTM Eng 团队之所以能把这些 agent 搭得这么快，一个核心原因就是：Vercel 平台本身已经把“基于我们自己的框架调用基础设施，再把 agent 很快推到生产环境”这件事做得足够简单了。

Lenny Rachitsky你们在这件事上真是有一种很漂亮、也很不公平的优势。

Jeanne DeWitt Grosser确实，做这件事很爽。我得说，这家公司是我见过最会“吃自己狗粮”的公司。我们常说一句话：`Vercel builds Vercel with Vercel`。

所以大家会天然去想：我们怎么用自己的产品解决自己的问题？而这样做的结果，一方面会让我们更理解客户真正想要什么，另一方面也会更快发现：我们的产品还缺什么、哪里还可以做得更好。

Lenny Rachitsky顺着这个话题，我还想追问一个你反复提到的观点。很多人都说，你会把 go-to-market 当成一个产品来思考。我们听众里有很多本身就是产品 builder，我觉得这是个特别好的框架。你会怎么解释“把 go-to-market 当成产品来做”？

Jeanne DeWitt Grosser我大概在十多年前就形成了这个认识。

我大学毕业后的第一份工作是在 2004 年做 Gmail。Gmail 是 4 月 1 日上线的，我 6 月 1 日加入。当时 Gmail 真的是一种非常惊人的创新，一个巨大的 JavaScript 应用，在那个年代几乎没人这么做；它还直接给你 1GB 存储空间。Yahoo Mail 花了一整年才追上，Hotmail 和其他产品更久。所以那时候，Gmail 和第二名之间的技术代差非常大。
但再过了十年，随着云计算的发展，很多过去根本做不了的事情都能做了。我开始意识到：软件本身正在一点点商品化。既然纯技术差异在收窄，那公司还能靠什么拉开差距？
我开始往技术之外想。很多时候，我们买东西，不只是因为功能，也因为“感受”。于是我慢慢形成一个判断：如果产品彼此只差一点点，那么“你被卖给的体验”会越来越成为差异化来源，甚至直接影响购买决策。
如果你相信这一点，你就会特别重视客户的购买旅程，要把它设计成一连串很有辨识度的体验。我们当年在 Stripe 做了很多这样的事，现在也在 Vercel 复制这套思路。
比如在很多公司的销售流程里，客户被 qualify 之后，销售的第一通电话通常是 discovery call。说白了，就是我来问你很多问题，想弄清楚你的痛点、预算权在哪里、谁能拍板，等等。
但对客户来说，这种体验很多时候挺无聊的，因为你本质上是在被“电话考试”。
于是我们当年在 Stripe 做了个改动：第一场会不做传统 discovery，而是做白板会。我们会和客户一起把他们的支付架构画出来，把所有藏在底层、支撑他们收款和交付客户结果的系统都画清楚。
通过这个过程，我们当然能学到很多，比如他们现在的技术栈是什么、我们要替换谁、要跟谁竞争、价值点到底在哪；但客户自己也能学到很多，因为很多公司其实从来没有把自己的架构真正画出来过。
所以他们离开这场会时，会带走一个实际可用的资产，也会产生一种感觉：这个人很合作，而且是真的在认真帮我建立一套理解问题的心智模型。类似这样的设计，我们还做过不少。
所以我说“把 go-to-market 当成产品来做”，本质上就是：从客户第一次知道你这家公司开始，一直到五年后依然高度留存、深度合作的阶段，整条旅程都应该被设计成一组体验。
这些体验可以是平的、冷的、交易性的、无聊的；也可以是有人味的、个性化的、独特的。
我们做的事情，就是把这条路径一段一段画出来，想清楚怎么把产品能力带进来，怎么让过程更有人味。最终如果做得好，它带来的就不只是一次成交，而是一个长期客户。

Lenny Rachitsky我特别喜欢那个白板会的例子。还有没有别的做法，是你们真正用过、而且效果也很好的？

Jeanne DeWitt Grosser有。另一个我们在 Stripe 建立起来、我后来也带到 Vercel 的原则，是：无论客户最后买不买，每一个触点都尽量给到价值。

因为就算这次没买，你也经常会发现，等他们三四年后进入下一轮采购周期，又会回来。我在 Stripe 待了九年，所以这种事情看过非常多。很多当年没买的客户，过了半个十年之后又回来了，而且最后真的买了。
所以在 Vercel，我们会做的一件事是：主动给客户一些即时洞察。互联网上其实有不少数据，可以帮助大家理解网站性能；而网站速度又会影响 SEO，SEO 又会影响 AEO。现在大家都在关心 AEO。
所以我们在第一次触达时，往往会直接先给对方一些信息：你现在的网站表现到底怎么样？绝对值如何？和同行相比处在什么位置？
理想情况下，这会勾起你的兴趣，让你愿意继续深入了解我们；但即便没有，你也已经拿到了一些本来未必注意到的洞察。至少它会让你开始重新想一件事：我现在这套技术栈，真的是最优的吗？

Lenny Rachitsky我听下来，你说“把 GTM 当成产品来做”，其实和产品经理思考产品体验是同一套逻辑。就是从用户视角去看整条路径：第 1 步、第 2 步、第 3 步……怎样把每一步都设计得足够好，让他愿意继续往下走。只是这里的“用户”变成了潜在客户。

Jeanne DeWitt Grosser对。核心是：让它像一段体验，而不是一笔交易。

Lenny Rachitsky而不是那种“销售冲上来硬卖你东西”的感觉。

Jeanne DeWitt Grosser没错。

Lenny Rachitsky那我们继续往更战术的层面走。现在如果有人想让更多人注意到自己的产品、愿意掏钱买单，你觉得哪些 go-to-market tactic 现在依然特别有效？

Jeanne DeWitt Grosser有一个和刚才讲的思路是连着的，就是：你能不能围绕你的产品，或者围绕客户当前“其实没那么理想的状态”，拿出一些真正独特的洞察？

所以我确实觉得，愿意在数据上做投入，把这种洞察挖出来，是很值得的。
另一个我觉得很朴素、但经常做得不够的事是：很多好公司会认真写 docs，这当然很好，但很多团队做到这里就停了。
可如果你卖的是稍微大一些的客户，仅有文档通常不够。比如 AWS 有 well-architected guide、各种 blueprint。很多客户，尤其是大客户，真正想知道的是：在“我的这个具体环境”里，到底应该怎样以最佳实践的方式把你的产品接进去。
一个很典型的 Stripe 例子是 marketplace。像 Lyft、Instacart、DoorDash 这类公司基本都跑在 Stripe 上，所以 Stripe 非常清楚 marketplace 的支付体系该怎么搭才是最优。
所以当你去卖一个 marketplace 客户时，如果只是说“我们有文档，你自己去看”，他们其实不会满意。因为他们心里想的是：所有 marketplace 都在用 Stripe，我不要通用文档，我要的是你直接告诉我，marketplace 的支付架构到底怎样设计最好。
所以我觉得这也是一个非常关键的动作，尤其是当你的目标客户已经不再只是单个开发者、独立创业者时，更要往这个方向走。
还有一个也许不完全算 tactic，但我觉得对还处在 founder-led sales 阶段的创始人非常重要：一定要学会做高质量的 discovery。
我经常看到创始人一聊到产品就很兴奋，问到一个问题，马上就觉得“这个我能帮你解决”，然后立刻开始讲方案。
但真正优秀的销售，在一场对话里通常说话时间不到一半。因为他们一直在提问、追问，很多时候是在帮助客户自己得出结论。
所以你得学会做 five whys，往深里挖，而不是立刻进入“解决问题模式”。别人问你一个问题时，你很多时候不应该马上回答；更好的做法是，先围绕这个问题再问一个问题，弄清楚上下文，然后再回答。
把这件事练好，我觉得会非常拉开差距。

Lenny Rachitsky所以最后这个建议，其实很多人都该学：少说一点，多听一点。

Jeanne DeWitt Grosser对。

Lenny Rachitsky回到你刚才第一条建议，也就是分享独特洞察、指出客户当前状态其实不够理想。有没有更具体的例子？比如你是怎么让别人意识到：如果继续这样做，他们其实错过了什么，而 Vercel 或 Stripe 能让他们变得更好？

Jeanne DeWitt Grosser以 Vercel 为例，我刚才已经提过一点，我可以讲得更具体些。

比如性能这件事，你可以直接去看 `Core Web Vitals`，它能告诉你你的网站哪些地方够快、哪些地方加载不对、哪些地方表现有问题。这些数据理论上任何人都能查。
但我们能进一步做的是，帮你把这些指标和同行做 benchmark。这个我们已经对外做了不少。
另一个我们投入很多的方向，是帮助客户理解 MCP server 到底是什么、什么时候值得用。现在大家都在聊这个概念，但很多人其实不知道应该怎样把它放进自己的产品体系里。这个方向我们也做得很深。
再比如 AEO，严格说它和 Vercel 不是完全直接对应的。

Jeanne DeWitt Grosser但我们的逻辑是：性能会影响 SEO，SEO 又是 AEO 的输入之一。虽然 AEO 不是 Vercel 唯一、也不是最直接的卖点，但我们自己在这件事上研究得很深，也确实觉得比很多人理解得更透。

所以我们会花很多时间把这些 AEO 洞察分享出去。这样做本质上也是在建立一种信任关系。有些人会因为参加这些 AMA、看了这些内容，进一步意识到：“原来你们不只是讲概念，是真的懂。”于是自然会想到，那 Vercel 也许真的能帮我把性能做好。
当然，也有很多人不会马上买。但他们至少会留下一个印象：这家公司挺有洞见，值得我继续关注。等未来某个时刻，又看到一个触发点，他们可能就会开始认真研究 Vercel 的某个具体能力。

Lenny Rachitsky这和我最近另一场播客挺呼应的。我前阵子请了 Jen Abel 来聊销售技能，其中有一个观点是：别老盯着“我们帮你解决什么痛点”，而要更多去讲“用了我们之后，你会比竞争对手强在哪里”。比如用 Vercel，你会拿回速度优势，在 AEO 上不再吃亏；或者你能把支付系统架构搭到行业顶级水平。这个说法你认同吗？

Jeanne DeWitt Grosser认同。不过我之前还听过一个数据，应该是个取整后的说法，不一定百分之百精准，但大意是：80% 的客户买东西，是为了避免痛苦或降低风险；真正为了放大上行空间而买单的，大概只有 20%。

这点对创业者其实很重要。我们都喜欢讲“可能性的艺术”，讲未来能做到多酷、能打开多大的空间。创始人之间很容易被这种叙事打动，因为大家本身就偏愿景型。
但对更多普通客户，尤其企业客户来说，他们真正关心的往往是：我下个季度的营收目标会不会完不成？我会不会被竞争对手甩开？品牌会不会受损？
所以很多创业公司要完成这个转弯其实挺难的，因为会觉得这种表达有点“不像自己品牌”。但现实是，适度唤起这种风险意识，确实更能驱动购买。
你要么让客户意识到：我现在可能并没有处在一个安全或有优势的位置；要么通过很好的提问，让他们自己看清楚：原来我具体差在这里，而你正好能帮我补上。

Lenny Rachitsky这个统计非常重要。我们之前在播客里也聊过，很多购买行为本质上是在“降低职业风险”，也就是不想把事情搞砸。

比如说，公司决定引入 Stripe，这其实是个巨大的职业下注。如果项目没落好，你的职业声誉会受损，你老板会不爽，公司还会被拖慢。所以很多购买决策背后，不只是“我有个问题需要解决”，而是“我绝对不能把这件事做砸”。

Jeanne DeWitt Grosser完全同意。

Lenny Rachitsky继续讲 tactics。我知道你很重视 segmentation，也经常帮别人理这个问题。很多创始人都知道自己得做 segmentation strategy，但一落地就容易糊。你能不能给大家一个 segmentation 的入门框架？为什么它重要？具体该怎么开始？

Jeanne DeWitt Grosser所谓 segmentation，本质上就是：你怎么把这个世界上的公司切开，切到每一类在购买方式上都确实不同。

我分别用 Stripe 和 Vercel 的例子来讲。
最常见的一种分法，是按公司规模切成 small、medium、large，这本身完全合理。小公司通常只有一个决策人；中等公司可能是一个小团队；大公司就会变成复杂委员会决策。所以 SMB、mid-market、enterprise 的购买流程确实不一样。
但如果你只停在这里，通常还是不够的。因为你还要继续问：在我的产品里，还有哪些因素也会改变销售方式？
Stripe 当时进一步有两种切法。你可以把 segmentation 想成一张图。X 轴是规模，也就是 small / medium / large；Y 轴是 growth potential，也就是增长潜力。
这个维度对 Stripe 很重要，因为 Stripe 是 consumption-based business。一个年增长 200% 的客户，对 Stripe 来说，显然比一个年增长 8% 的客户更有价值。
所以我们会愿意把更多时间、更多预算放在那些增长更快的客户身上。这是第一层，决定你该重点追哪些人。
在 Stripe，我们还有另一层切法，就是 business model。你是 B2B、B2C、B2B2B（比如平台）还是 B2B2C（比如 marketplace）？为什么这个重要？因为不同业务模式，对产品组合的需求完全不同。
如果你是 B2B，你大概率需要 business payments。信用卡对 PLG 或自助购买可能够用，但你终究还会需要 ACH、wire transfer 这些能力，而且如果你有持续性业务，你多半还会想要 Stripe Billing。
如果你是 B2C，那你要的是消费者支付能力，比如 Apple Pay 会非常关键。
如果你是平台或 marketplace，你大概率会买我们的 Connect 产品。
也就是说，这样切完之后，我们就能做出更有针对性、也更可复制的销售打法。
Vercel 也差不多。首先还是 small / medium / large，对应购买复杂度；也同样会看 growth potential，因为我们也是消费型收入模型。
但对 Vercel 来说，我们还会再叠几个维度。比如一个很容易观测的指标是流量，也就是网站 traffic。Google 会发布 `CrUX` 分数，它基于 Chrome 的大量数据，所以能大致知道：Lenny 的网站有多少流量，Jeanne 的网站有多少流量。

Lenny Rachitsky几百万。

Jeanne DeWitt Grosser对，就是这个意思。如果一家公司的团队规模不大，但网站流量非常高，那对我们来说，这个销售就会更复杂、收入潜力也更高，所以我们会把它往上提。

OpenAI 就是个很好的例子。它现在到底多少员工我不确定，假设是 3000 人，按很多公司的标准，也就算 mid-market；但它却是全网流量前 25 的网站之一。
对 Vercel 来说，这种客户显然就不该按普通 mid-market 处理，而是要直接按 enterprise 来做，因为我们必须用更深入、更重的销售流程去跟。
还有一个我们会叠加的维度，是 workload type，也就是业务负载类型。
比如你是电商公司，那整个销售语言都不一样。你会聊 product listing page、product description page、order management system 这些东西。
但如果你是 crypto 公司，情况又完全不同，你可能从头到尾都跑在 AWS 上。
这些信息都会帮助我们进一步生成一套非常不同的购买内容和销售叙事。

Lenny Rachitsky这太好了。所以你本质上是在把整个公司宇宙拆开，像你在 Stripe 时做的那样，去判断哪些公司最可能成为好客户。而你最后定义出来的，就是一组和“高价值客户概率”强相关的属性。

Jeanne DeWitt Grosser对。

Lenny Rachitsky那你会建议大家也用这种 XY 轴方式来开头吗？还是说也可以用别的方法，比如一个有五列字段的表格？到底该怎么起步？

Jeanne DeWitt GrosserX/Y 轴当然有它的合理性。比如规模，大概率会影响多数购买决策；而且在今天，很多业务又都带有 consumption 特征，所以有些维度确实是相对通用的。

但我真正想说的是：你得先回到自己的业务。
我到 Vercel 之后，因为无论产品、市场还是产品组合，对我来说都算新领域，所以我有很多要补的东西。但我在前 30 天里最先做的一件事，就是和这里负责数据科学的 Abhi 坐下来问：到底什么因素在驱动收入？
也就是，你能不能在客户还没买之前，就从一些可观测属性判断：这个客户更可能给我们付 10 万美元，还是 100 万美元？这通常就是 segmentation framework 的一部分。
然后再继续问：哪些属性会让我们在某类客户上反复赢？我们最终就是这样推出来：`CrUX rank` 会非常重要，因为客户付给 Vercel 的钱和它的流量高度相关；而 workload type 也同样非常重要。
对 Vercel 来说，这个分析特别有意思的一点是，我们会突然看清楚：哦，原来我们在 e-commerce 里的渗透率很高。这其实也不算意外，因为我们就是帮你把网站跑得更快，而电商网站对性能极度敏感。
但当时如果你去看 enterprise SaaS，公司里其实没有太多在用我们。按直觉你会以为：既然 Vercel 是 front-end cloud，又特别 developer-oriented，那软件公司不是应该天然适配吗？
可现实是，大多数 enterprise SaaS 公司的产品，都是在 Vercel 出现之前就搭好的。你要让他们把 200 万行代码迁过来，这可不是小工程。
所以这个框架会帮助我们真正看清：我们现在哪些地方在赢，哪些地方没赢。
而且这也会随时间变化。比如今天，在 enterprise SaaS 公司里，我们就开始明显看到对 AI cloud 的兴趣，因为这类公司往往会最早尝试把 AI-native 功能加进现有 SaaS 应用里。
所以 segmentation 不是一次性动作，它是在不断帮你判断：不同阶段，应该把力气打到哪里。

Lenny Rachitsky所以你其实是在对“哪些东西有效”做某种回归分析，然后找出那些和成功最相关的属性。

我平时给创始人的一个小启发是：先试着想 3 个属性，把目标客户快速缩小。比如一家 A 轮公司、某种投资人背景、再加某个业务模型之类。你觉得这种“三个属性先起步”的经验法则合理吗？

Jeanne DeWitt Grosser我觉得挺合理的。再多过三个，通常就已经太细了。现实一点讲，如果你团队里只有 5 个销售，你总不能真的切出 5 个完全不同的 segment，再给每个人分一个吧？

所以三个维度，基本已经是一个人脑可以稳定推理、组织也能执行的复杂度。
另外还有一点我特别想强调：很多人觉得 segmentation 只是 go-to-market 团队的事情，但我真心觉得，它其实是整个公司的事情。
在 Vercel，新员工入职第一周我会亲自讲一段内容。我们有个公司价值观叫 `KYC`，也就是 `Know Your Customer`。我负责讲的，就是这一部分。我会把我们的 segmentation framework 讲给所有新人听，也会解释我们的客户群体是怎样映射到这些 segment 里的。
为什么这件事重要？因为我希望新来的产品经理走出那个房间以后，在构思一个新产品时，会先问自己：我现在做这个新的 backend 产品，到底是给谁的？是给 enterprise，还是给 startup？我对“自己想赢哪一类客户、为什么想赢”有没有明确观点？
如果你从一开始就在产品层面把这件事想清楚，后面再去和 go-to-market 团队协同时，大家就会天然说同一种语言，也更容易一起判断：这个东西到底该怎么推向市场，应该调动哪些情绪、打哪些价值点。

Lenny Rachitsky这正好就引到我想聊的另一个话题。很多和你共事过的人都说，你特别擅长搭建一种能和产品、工程协作得非常顺的 GTM 团队。

我念一段你前同事 Kate Jensen 的评价。她说，你的超能力是“搭建一个不会让工程师觉得那是销售团队的销售组织”。所以她建议我问你：到底要怎么做到这一点？什么样的要素，才能让工程和产品团队真心愿意跟销售一起工作？

Jeanne DeWitt Grosser我一直给销售团队一个检验标准：如果你是我组织里的 account executive，我把你放到我们公司 10 个工程师面前，他们应该至少要花 10 分钟，才会发现你其实不是产品经理。

我想传递的意思是：你必须有极深的产品理解。
原因有两个。第一，这会让你在产品和工程团队那里建立可信度。第二，我一直相信，世界上最好的 GTM 团队，一半是 revenue engine，另一半其实是某种形式的 R&D。
为什么我会强调后者？因为你想，如果是产品组织，你可能会有 UXR 团队在做研究，产品经理也理应不断去和客户对话。
那如果我有一个 20 人的销售团队，我们一周能接触多少客户？这个量是非常大的。
所以如果我们能把这些客户反馈高质量地翻译成真正的 signal，再把它喂回 roadmap，那销售团队其实可以成为产品管理组织的延伸。
但这件事的前提是，你得特别擅长区分 signal 和 noise，知道什么只是一个应该靠 objection handling 化解的阻力，什么又是真正值得抓住的市场机会。
我觉得这些能力，确实帮了我们很多。

Lenny Rachitsky作为一个产品经理，或者说曾经的产品经理，我太喜欢这个说法了。我现在都不知道自己算什么了。但我真的很喜欢这样一种状态：一个销售坐在你面前，你几乎分不清他到底是销售还是产品经理。

传统上最经典的问题就是，销售团队总会来提一堆 feature request，而 PM 则得不断往回顶，判断这些东西到底合不合适。所以你这套方法的核心之一，似乎就是让销售真正理解产品的整体逻辑。

Jeanne DeWitt Grosser对。你想要的是一个能像 general manager 一样思考的销售组织。

它不只是为了把 deal 做成，而是真的在帮助公司把业务做大。所以它知道什么时候该说“不”；知道什么时候这只是个 objection，需要通过销售动作去处理；也知道什么时候应该说：“我已经连续三通电话都听到这件事了，我认为这真的是一个很大的 unlock，会显著提升我们的竞争力，而且可能是市场上别人还没在做的东西。”
所以你在招人时，需要找的是那种既有销售能力、又具备产品视角的人。

Lenny Rachitsky我太喜欢了。再念一句评价，这次来自 Claire Hughes Johnson，也是播客前嘉宾，非常厉害的销售 leader，曾在 Stripe 和你共事。

她说，Jeanne 可能是她见过最会和产品、工程建立连接的 GTM 负责人，对产品理解最深，也最能给合作方提供真正有价值的输入。
听起来，这里还有一个关键点，就是销售不只是对产品和工程说“帮我做这些”，而是真的把自己当成一个 partner。

Jeanne DeWitt Grosser本质上，公司战略就是 product strategy 和 go-to-market strategy 的交汇。

作为一个 GTM leader，我每天都在想的是：怎么更高效地赚到更多钱？而通常这件事成立的前提，是你得有一个真正能赢的产品，而且商业化做得足够好。
所以我会非常主动地去思考产品策略，也会非常主动地去思考定价策略。因为如果这两件事是最优的，你赢单的概率就会更高，摩擦也会更少。
也就是说，作为一个 revenue leader，你得戴上一顶 GM 的帽子，而不能只想着“我怎么卖出去”。你还要想：我每天从客户那里拿到的这些洞察，怎样才能反过来让公司的整体战略更有效。

Lenny Rachitsky说到产品，我想稍微换个方向。PLG，也就是 product-led growth，有一阵子特别火。那时好像所有人都在说：“必须做 PLG，这才是唯一正确道路，纯销售已经不行了，未来就是 PLG。”

现在这种声音似乎弱下来了。当然还是有很多公司靠 PLG 增长。你现在怎么看 PLG？什么情况下，一家公司应该认真把它当成增长主轴？

Jeanne DeWitt Grosser我觉得，对很多公司来说，在早期做 PLG 仍然非常合理，除非你从第一天起就非常明确地在做 enterprise-only 产品。

比如 Sierra 这种公司，他们一开始就是盯着 Global 2000 去打，或者至少是极其接近那一层的大客户。这种情况下，PLG 的帮助就不会太大，因为他们从 day one 就是在争夺八位数的大单。
但对很多产品来说，最初瞄准的其实是 startup 用户，然后再逐步补功能，慢慢往上打更大的市场。所以我觉得 PLG 依然非常重要。它是 Vercel 增长的重要驱动力，当年也是 Stripe 增长的重要驱动力。
大家真正搞错的地方在于：PLG 通常是有天花板的。
一般不会有人通过一个纯自助流程，直接给你 100 万美元。所以如果你想持续保持增长，最终你的 deal size 就得越来越大。
而很多公司卡住的点恰恰在于：他们在 PLG 上停得太久，没有及时把销售能力补上。因为建立一套可复制的销售流程，本来就需要时间。
刚开始，你可能吃的是 inbound；之后你还得把 outbound 也建起来。而 outbound 要想变成一个稳定、可预测的引擎，通常要更久。
所以很多公司撞墙，不是因为 PLG 不行，而是因为他们太晚才补上销售这条腿。

Lenny Rachitsky所以你的意思是，几乎所有公司最终都得建立销售组织。区别只是，有些公司先从产品驱动起步，后来再加销售；有些公司一开始就带着销售起步。

Jeanne DeWitt Grosser对，我基本认同。

也许会有一些垂直 SaaS 的大平台，长期看起来更偏 SMB，但即便如此，它们最后通常也会长出一个 velocity sales team。
所以我现在确实想不出哪家千亿美元级公司，是真的只靠 PLG 的。

Lenny Rachitsky对，感觉哪怕你已经长得很快，如果不做销售，还是会把很多钱留在桌子上。像 Atlassian 就是长期 PLG 的代表，但最后也还是走向了销售。虽然我不知道“屈服”这个词是不是恰当。

好，你刚才提到定价。我知道你对 pricing 和 pricing strategy 很有想法。如果有人正在思考该怎么给产品定价，你会先给他哪几个建议？

Jeanne DeWitt Grosser我觉得第一件事，就是你要把定价当成产品来思考。

定价不是一个附属动作，它本身非常重要。你要不要真的理解客户价值是从哪里来的？你要不要真的理解你的成本发生在哪？你有没有把这两件事尽可能聪明地对齐？
现在有太多公司存在严重低估自己价值的情况，你明明提供了很大的价值，却不敢按这个价值收费。
还有一种很常见的问题是，大家默认“应该有个 freemium”，但这件事其实根本没被当成一个严肃策略来设计。
Stripe 当年就有个例子。我们很多年前上线 Stripe Billing 时，顺手就加了 freemium，因为大家都这么做。后来我们回头一看，发现：其实集成 Stripe Billing 这件事本身是有成本的，你一旦真集成了，大概率就会继续留下来。
于是我们把 free trial 直接砍掉了，结果几乎没有负面影响。
Vercel 最近也经历了类似的定价调整。我们的底层其实是一个 consumption-based model，但早期我们把它打包成了看起来更像 SaaS 的价格。随着功能越来越多，这种打包方式开始不合适了。
于是我们做了一次 unbundling。去年 8 月，我们还做了一次比较大的价格调整。我们有一个 enterprise 层，也有一个 pro 层。按名字你就知道，enterprise 本来就是卖给 enterprise 的。
但我们后来发现，enterprise 层里差不多有一半用户其实是 startup。这说明什么？说明 enterprise 这个包里，有些能力其实是 startup 也非常想要的。
于是我们把其中很多功能从 enterprise 包里拆出来，改成可以在线 self-serve 购买。结果也正如你所预料的，大家真的会买。
这带动了我们 PLG funnel 很多增长。对 startup 来说很好，因为他们可以非常高效地直接买到想要的东西；对我们也很好，因为中间不需要一定有人工介入。
所以，把这些 pricing knob 调准，既关系到客户体验，也直接关系到收入结果。

Lenny Rachitsky在进入精彩的 lightning round 之前，我再问最后一个组合问题。我听说你对销售激励机制，也就是 sales comp，有一个和主流不太一样的看法；另外，你对销售招聘也有自己的偏好。能不能一起讲讲？

Jeanne DeWitt Grosser我对 sales comp 的纠结在于：它当然强调 pay for performance，这点我完全支持；而且销售本来就是一个非常量化的岗位，这也很好。

但问题是，它会让组织变得没那么灵活。因为你基本上得提前 12 个月决定：我今年看重哪些事、奖励哪些行为。
尤其在现在这个环境里，你真正重视的东西随时可能变。Vercel 今年就是一个好例子。我们年初写销售计划的时候，AI cloud 还不存在；当时卖的是 front-end cloud 和 VZero。结果年中 AI cloud 突然出来了。
当然，我们还是找到了各种方式去激励这部分销售，但我确实觉得，如果你的销售计划设计得太完整、太结构化，组织在需要转向、创新时就会变得没那么灵活。
所以我有个有点“逆主流”的看法：我一直在想，能不能既保留销售这种强激励、强结果导向的好处，又给组织留下足够多“改变主意”的空间。
因为我觉得现在很多公司都很难做真正靠谱的年度规划，这就是其中一个原因。
至于人才画像，我一直都很相信“组合配置”。
我非常坚定地认为，销售是一门技能，所以团队里一定要有真正做过销售的人。但与此同时，我也很喜欢搭配一些非传统背景的人，尤其是咨询或投行背景。
因为这类人通常特别擅长销售里偏量化、偏分析的部分，也更适合做那种咨询式销售，而这正好和我们前面聊到的方向是一致的。
所以我常常会发现，当这些人被混编进团队后，会发生很有意思的双向学习。
咨询 / 投行背景的人会意识到：“等等，原来销售真的是一门技能，而我以前并没有这套能力。”于是他们会向那些真正有 account executive 经验的人学习。
反过来，那些传统 AE 也会从他们身上学到更多，比如：怎么去看一家公司的 P&L？怎么和 CFO 对话？怎么把 TCO 分析讲得更有说服力？
这样一来，团队内部就会形成一个丰富得多的学习环境，大家会不断互相碰撞想法。

Lenny Rachitsky太棒了，我很喜欢这个策略。最后一个问题，在进入 lightning round 前，你还有什么特别想留给听众的吗？

Jeanne DeWitt Grosser天哪，我感觉我们已经聊得非常全了。

Lenny Rachitsky好，那说明我们成功了。

Jeanne DeWitt Grosser对，这题你把我问住了。

Lenny Rachitsky这就是目标。接下来进入我们非常激动人心的 lightning round。我会很快，因为我知道你也得走了。我只问两个问题。

Jeanne DeWitt Grosser好。

Lenny Rachitsky先问一句你的人生格言。有没有一句你经常会回头想起、在工作和生活里都很好用的话？

Jeanne DeWitt Grosser有。我后来才意识到，自己原来常常会重复说几句话。因为当你离开一家公司时，别人总会告诉你，什么东西最让他们记住。

其中有一句我应该算是很常说的。小时候我妈妈总对我说：`When the going gets tough, the tough get going.` 大意就是，越是难的时候，越要顶上去。
销售工作里，你总会遇到某个季度没达标、节奏不对的时候。所以这句话我经常会拿出来提醒自己。
另外还有一句我妈妈也总说：`Where there's a will, there's a way.` 也就是，只要你真想找路，路总能找出来。
所以我一直很相信，就算眼前的路径还不清楚，你也总能选择继续往前找出一条路。

Lenny Rachitsky我很喜欢。最后一个问题。我看到你大学时曾经是个很有竞争心的跳水运动员。我很好奇，这段经历里有没有什么被你一路带到了今天，也帮助你取得现在这些成绩？

Jeanne DeWitt Grosser先说明一下，我在队里通常是三个选手里的第三名。

Lenny Rachitsky第三名也不错啊。

Jeanne DeWitt Grosser我大学里能坚持跳，就已经差不多是那段运动生涯的全部高光了。

但跳水是一项非常强调精确度的运动，也是一项极其重复的运动。更重要的是，它还有一个很“残酷”的特点：如果你某次失误，整个人平拍在水面上，游回池边的时候背上都已经开始起红印了，你依然会 100% 被要求立刻回到跳板上，把同一个动作再做一遍。
我觉得这里面有很多东西都能迁移到工作和销售里。
对我来说，我对“做到优秀”这件事有一种近乎执念的追求。而销售本身又是一门讲究可复制性的工作。你怎么把结果做得可预测？你对 forecasting 的准确度到底能做到多高？这些我都会非常在意。
另一方面，销售里你会不断被拒绝。所以我以前还听过一个销售教练说过一句话：`yeses are great, nos are great, maybes will kill you.`
也就是说，答应当然很好，明确拒绝其实也很好，最可怕的是模棱两可。
所以你得把“no 也是好东西”这件事真正内化，因为它给了你数据，而有了数据，你就能继续动作。

Lenny Rachitsky这是个特别鼓舞人的结尾。Jeanne，非常感谢你今天来。

Jeanne DeWitt Grosser谢谢你邀请我，Lenny。聊得很开心。

Lenny Rachitsky大家拜拜。

感谢收听。如果你觉得这期内容有价值，欢迎在 Apple Podcasts、Spotify 或你常用的播客应用里订阅，也欢迎打分或留下评论，这会帮助更多人发现这档节目。
你可以去 `lennyspodcast.com` 查看往期节目，或者了解更多播客信息。我们下期见。

Jeanne DeWitt Grosser所以这算是我在 sales comp 上一个有点逆风的看法：我一直在想，能不能既保留销售激励的上行空间，让人有动力冲结果，毕竟这是个非常量化的岗位；同时又保留足够的灵活性，让组织在必要时可以调整方向。

因为我觉得，现在很多公司做年度规划本来就已经很难了。
至于人才画像，我一直很看重“组合多样性”。
我非常相信，销售是一门技能，所以团队里一定要有真正有销售经验的人。但与此同时，我也觉得把一些非传统背景的人和他们搭在一起很有价值，尤其是咨询和投行背景。
这类人往往特别擅长销售里偏量化、偏分析的部分，也更容易切进那种 consultative selling 的状态，这和我们前面聊到的方向其实是一致的。
所以我经常会看到一种很有意思的互补：咨询 / 投行背景的人会突然意识到，“等等，原来销售真的是一门技能，而我原来并不具备。”然后他们就会去向那些有 account executive 背景的人学习。
反过来，那些 AE 也会从他们身上学到很多，比如：怎么理解一份 P&L？怎么和 CFO 对话？怎么把 TCO 分析讲得更有说服力？
所以当你把这些不同画像的人混在一起时，团队内部会形成一个更丰富的学习环境，大家会不断互相借力。

Lenny Rachitsky太棒了，我很喜欢这个策略。最后一个问题，在进入我们激动人心的 lightning round 之前，你还有什么想留给听众的吗？

Jeanne DeWitt Grosser天啊，我感觉我们已经聊得非常全了。

Lenny Rachitsky那很好，说明我们完成任务了。

Jeanne DeWitt Grosser对，这题还真把我问住了。

Lenny Rachitsky这就是目标。那接下来进入我们非常激动人心的 lightning round。我会很快，因为我知道你也要赶时间了。我只问两个问题。

Jeanne DeWitt Grosser好。

Lenny Rachitsky第一个问题，直接问你的人生格言。有没有一句你经常回头想起、在工作和生活里都觉得特别有用的话？

Jeanne DeWitt Grosser有的。我后来才发现，自己其实有几句话是经常挂在嘴边的。因为当你离开一家公司时，大家往往会告诉你，他们记住了你说过什么。

其中有一句我应该算是很有代表性的。小时候我妈妈总对我说：`When the going gets tough, the tough get going.` 大概就是，越是局面艰难，越要顶上去。
销售里你总会遇到某个季度节奏不对、离目标差一截的时候，所以这句话我其实挺常拿出来提醒自己。
还有一句我妈妈也常说：`Where there's a will, there's a way.` 只要你真想找到路，就总能找到路。
所以我一直觉得，即便当下前面的路还不够清楚，你依然可以选择继续往前，把路找出来。

Lenny Rachitsky我很喜欢。最后一个问题。我读到你大学时是个很有竞争心的跳水运动员。我很好奇，那段经历里有没有什么被你一路带到了今天，也帮助你取得现在这样的成绩？

Jeanne DeWitt Grosser首先我要说明一下，我在队里通常是三个选手里的第三名。

Lenny Rachitsky第三名也不差啊。

Jeanne DeWitt Grosser我能在大学继续跳下去，基本就已经是那段运动生涯的全部了。

但跳水是一项非常讲究精确度的运动，也是一项高度重复的运动。更重要的是，它还有一个特别残酷的地方：如果你某次整个人平拍在水面上，游回池边时背上已经开始起红印了，你依然会被要求立刻重新走上跳板，再把完全一样的动作做一遍。
我觉得这件事和工作、尤其是销售，非常像。
对我来说，我对“做到优秀”这件事一直有点执念。而销售本身又是一门讲究可复制性的工作。你怎样把结果做得更可预测？你的 forecasting 到底有多准？这些我都会特别在意。
另一方面，销售里你会收到很多个 no。
我以前还听一位销售教练说过一句话：`yeses are great, nos are great, maybes will kill you.`
也就是说，答应当然很好，明确拒绝其实也很好，最麻烦的是模棱两可。
所以你得真正习惯“no 也是一种好结果”这件事。因为它给了你数据，而有了数据，你就可以继续行动。

Lenny Rachitsky这真是一个特别鼓舞人、也很有力量的收尾。Jeanne，非常感谢你今天来。

Jeanne DeWitt Grosser谢谢邀请，Lenny。今天聊得很开心。

Lenny Rachitsky大家拜拜。

感谢你收听这期节目。如果你觉得这期内容有价值，欢迎在 Apple Podcasts、Spotify 或你常用的播客应用里订阅，也欢迎给我们评分或留下评论，这会帮助更多听众发现这档节目。
想看往期节目，或者了解更多信息，可以访问 `lennyspodcast.com`。我们下期见。