YouSaid · the spoken record

Jeanne DeWitt Grosser

lines on the record: 88
first: 2025-11-30
most recent: 2025-11-30
sittings or episodes: 1
sources: podcast

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“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, you know, for me, I just have an obsession with excellence and within sales, sales is about replicability. How do you drive predictable outcomes? You know, 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, like you get a lot of no's in sales. And so, you know, another phrase that a sales guru said to me once or in a training was yeses are great, no's are great, maybe's they'll kill you. And so how do you get really comfortable that no is a great thing? Gave you data, and now you can go do something with it.”
2025-11-30 · Lenny's Podcast · What world-class GTM looks like in 2026 | Jeanne DeWitt Grosser (Vercel, Stripe, Google) · IDENTIFIED FROM THE TRANSCRIPT · source
“Well, I mean, first of all, I should say I was generally coming in third place out of three on my team. I managed to do it in college, but that was the extent of that career. So I do think, so diving as 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, like welts are forbidding on it.”
2025-11-30 · Lenny's Podcast · What world-class GTM looks like in 2026 | Jeanne DeWitt Grosser (Vercel, Stripe, Google) · IDENTIFIED FROM THE TRANSCRIPT · source
“I do. I actually have found that I'm known for saying a handful of things 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, you know, there's, 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, you know, I think you can always choose to find a path forward even when that's not super clear”
2025-11-30 · Lenny's Podcast · What world-class GTM looks like in 2026 | Jeanne DeWitt Grosser (Vercel, Stripe, Google) · IDENTIFIED FROM THE TRANSCRIPT · source
“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? You know, 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.”
2025-11-30 · Lenny's Podcast · What world-class GTM looks like in 2026 | Jeanne DeWitt Grosser (Vercel, Stripe, Google) · IDENTIFIED FROM THE TRANSCRIPT · source
“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 what 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 non-traditional backgrounds, in particular consulting.”
2025-11-30 · Lenny's Podcast · What world-class GTM looks like in 2026 | Jeanne DeWitt Grosser (Vercel, Stripe, Google) · IDENTIFIED FROM THE TRANSCRIPT · source
“I struggle with Sales Comp because it's all about pay for performance, which I'm obviously a fan of, but it is, 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 Versailles, 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, you know, when you have.”
2025-11-30 · Lenny's Podcast · What world-class GTM looks like in 2026 | Jeanne DeWitt Grosser (Vercel, Stripe, Google) · IDENTIFIED FROM THE TRANSCRIPT · source
“And actually, about half of the folks on Enterprise Skew were startups, which suggests that there's stuff in 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, you know, so now that's like 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, you know, getting all of these knobs really tuned is a key to both a great customer experience and optimal revenue outcomes.”
2025-11-30 · Lenny's Podcast · What world-class GTM looks like in 2026 | Jeanne DeWitt Grosser (Vercel, Stripe, Google) · IDENTIFIED FROM THE TRANSCRIPT · source
“What you do. And then we sort of looked at it and we're like, you know, 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 the free trial to zero downside. So, you know, that's another one. At Russell, we've been going through that transition where a consumption-based business model ultimately, but for 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 SKU. And if you looked at the enterprise SKU, it's called Enterprise for a Reason. It's meant to be sold to an enterprise.”
2025-11-30 · Lenny's Podcast · What world-class GTM looks like in 2026 | Jeanne DeWitt Grosser (Vercel, Stripe, Google) · IDENTIFIED FROM THE TRANSCRIPT · source
“Yeah. So I got a 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 because 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. Like a good example at Strape, we launched Stripe Billing years ago. It had a freemium strategy because that's.”
2025-11-30 · Lenny's Podcast · What world-class GTM looks like in 2026 | Jeanne DeWitt Grosser (Vercel, Stripe, Google) · IDENTIFIED FROM THE TRANSCRIPT · source
“Yeah, I would agree, there are probably some good examples of large vertical SaaS platforms that are SMB, but even they wind up with like a velocity sales team. So yeah, I don't know that I can think of like a hundred billion dollar company that's PLG only. Yeah, like you just feel”
2025-11-30 · Lenny's Podcast · What world-class GTM looks like in 2026 | Jeanne DeWitt Grosser (Vercel, Stripe, Google) · IDENTIFIED FROM THE TRANSCRIPT · source
“VI self serve flow. So at some point, if you want to sustain growth rates, 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.”
2025-11-30 · Lenny's Podcast · What world-class GTM looks like in 2026 | Jeanne DeWitt Grosser (Vercel, Stripe, Google) · IDENTIFIED FROM THE TRANSCRIPT · source
“I think a lot PLG 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? Like they are very clearly going after Global 2000 or something close to that. So 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 oversell's growth. It was a big driver of stripes growth. The thing that folks get wrong is it does typically have a ceiling. So people are generally not going to go give you a million dollars.”
2025-11-30 · Lenny's Podcast · What world-class GTM looks like in 2026 | Jeanne DeWitt Grosser (Vercel, Stripe, Google) · IDENTIFIED FROM THE TRANSCRIPT · source
“Know ultimately Company strategy is basically product strategy meets go to market strategy, right? And so I spend, I 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 you 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.”
2025-11-30 · Lenny's Podcast · What world-class GTM looks like in 2026 | Jeanne DeWitt Grosser (Vercel, Stripe, Google) · IDENTIFIED FROM THE TRANSCRIPT · source
“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 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 knew that nobody's doing. So, you know, I think that takes looking for a profile that both has sales skills, but also is going to think with that product mindset.”
2025-11-30 · Lenny's Podcast · What world-class GTM looks like in 2026 | Jeanne DeWitt Grosser (Vercel, Stripe, Google) · IDENTIFIED FROM THE TRANSCRIPT · source
“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 roadmap, 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.”
2025-11-30 · Lenny's Podcast · What world-class GTM looks like in 2026 | Jeanne DeWitt Grosser (Vercel, Stripe, Google) · IDENTIFIED FROM THE TRANSCRIPT · source
“The 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 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% sales team,”
2025-11-30 · Lenny's Podcast · What world-class GTM looks like in 2026 | Jeanne DeWitt Grosser (Vercel, Stripe, Google) · IDENTIFIED FROM THE TRANSCRIPT · source
“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 motions that we have in play?”
2025-11-30 · Lenny's Podcast · What world-class GTM looks like in 2026 | Jeanne DeWitt Grosser (Vercel, Stripe, Google) · IDENTIFIED FROM THE TRANSCRIPT · source
“Yeah, I think beyond three, you know, that's getting pretty detailed, and reasonably speaking, you're not going to cut you have five sellers. So what are you 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 join Versailles, I actually deliver and every new hires first week, one of our company values is KYC or your customer. And I deliver the KYC section.”
2025-11-30 · Lenny's Podcast · What world-class GTM looks like in 2026 | Jeanne DeWitt Grosser (Vercel, Stripe, Google) · IDENTIFIED FROM THE TRANSCRIPT · source
“Most of those companies built that SaaS offering before Vercel existed. And so migrating 2 million lines of code to Vercell, that's a big lift, right? So it helped us really understand where are we winning, where are we not? And now, as an example, like within SaaS companies and enterprise, we're actually seeing a lot of interest in the AI cloud because 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.”
2025-11-30 · Lenny's Podcast · What world-class GTM looks like in 2026 | Jeanne DeWitt Grosser (Vercel, Stripe, Google) · IDENTIFIED FROM THE TRANSCRIPT · source
“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 Racell is correlated with your traffic and then workload type was super important as well. So, you know, and for Rosell, when we did that, it was really interesting because, you know, we saw, wow, like we have a lot of penetration and e-com, not that surprising, actually, given that we, you know, drive highly performant sites and e-com having a super fast performance site really matters. But, you know, 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 have thought, okay, front-end cloud, very developer-oriented, of course software companies would be on us.”
2025-11-30 · Lenny's Podcast · What world-class GTM looks like in 2026 | Jeanne DeWitt Grosser (Vercel, Stripe, Google) · IDENTIFIED FROM THE TRANSCRIPT · source
“Probably something to be said for the XOY. Like, I do 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 like when I came to Brussels, new product market offering for me, it's a new market, right? 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 Abby who leads data science here. And, you know, said, okay, what drives revenue? So what are the things that you can look at ex ante about a customer to know this person's likely to pay us $100,000 versus a million? That's probably going to be part of a segmentation framework. And then similarly, okay, where can we, what attributes would we?”
2025-11-30 · Lenny's Podcast · What world-class GTM looks like in 2026 | Jeanne DeWitt Grosser (Vercel, Stripe, Google) · IDENTIFIED FROM THE TRANSCRIPT · source
“Open AI, 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, you know, lean in with a much more in-depth sales process. And then the other thing we layer on is workload type. So if you are an e-commerce company, that's going to be a very different sale. We're going to have to, 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 nets on AWS. And so again, that helps us start to then have a really different.”
2025-11-30 · Lenny's Podcast · What world-class GTM looks like in 2026 | Jeanne DeWitt Grosser (Vercel, Stripe, Google) · IDENTIFIED FROM THE TRANSCRIPT · source
“So basically, if you're a small company but you have super high traffic, that's going to be more complex. Vercel's going to make more money. And so we want to promote you. So great example of this would be OpenAI.”
2025-11-30 · Lenny's Podcast · What world-class GTM looks like in 2026 | Jeanne DeWitt Grosser (Vercel, Stripe, Google) · IDENTIFIED FROM THE TRANSCRIPT · source
“You know, 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 like the platform or the marketplace, you were going to buy or connect product. So it helped us basically then craft a more targeted and replicable sales. Roselle, sort of similar deal. 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 site gets a million X the amount that gene site does.”
2025-11-30 · Lenny's Podcast · What world-class GTM looks like in 2026 | Jeanne DeWitt Grosser (Vercel, Stripe, Google) · IDENTIFIED FROM THE TRANSCRIPT · source
“So small, medium, large. Y axis 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? EG a platform or B2B2 marketplace. And why is that relevant? Well, if you're B2B, you are going to need business payments, right? Credit card was useful for a PLG function or PLG sale, but you were going to need ACH wires, et cetera. And you probably had a recurring business. So you were going to want stripe billing.”
2025-11-30 · Lenny's Podcast · What world-class GTM looks like in 2026 | Jeanne DeWitt Grosser (Vercel, Stripe, Google) · IDENTIFIED FROM THE TRANSCRIPT · source
“Yeah, so 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 Brussel 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, you know, a small team and large. It's complex. It's a committee, et cetera. So the buying process does change across SMB midmarket enterprise. But if you stop there, you are likely missing, okay, 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-axis was size.”
2025-11-30 · Lenny's Podcast · What world-class GTM looks like in 2026 | Jeanne DeWitt Grosser (Vercel, Stripe, Google) · IDENTIFIED FROM THE TRANSCRIPT · source
“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 de-risk that.”
2025-11-30 · Lenny's Podcast · What world-class GTM looks like in 2026 | Jeanne DeWitt Grosser (Vercel, Stripe, Google) · IDENTIFIED FROM THE TRANSCRIPT · source
“Yeah, I was told this stat, it's round number, so I can't imagine it's entirely accurate. But, you know, 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, you know, everything we're going to enable in the future. It's very exciting. Everyone's visionaries, right? 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 having”
2025-11-30 · Lenny's Podcast · What world-class GTM looks like in 2026 | Jeanne DeWitt Grosser (Vercel, Stripe, Google) · IDENTIFIED FROM THE TRANSCRIPT · source
“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 Russell, 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 Vercell 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 when 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's the time I want to go investigate that aspect.”
2025-11-30 · Lenny's Podcast · What world-class GTM looks like in 2026 | Jeanne DeWitt Grosser (Vercel, Stripe, Google) · IDENTIFIED FROM THE TRANSCRIPT · source
“So with Russell, 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 that we then, 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.”
2025-11-30 · Lenny's Podcast · What world-class GTM looks like in 2026 | Jeanne DeWitt Grosser (Vercel, Stripe, Google) · IDENTIFIED FROM THE TRANSCRIPT · source
“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 whys, 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, right? So learned to be great at that, I think differentiates people.”
2025-11-30 · Lenny's Podcast · What world-class GTM looks like in 2026 | Jeanne DeWitt Grosser (Vercel, Stripe, Google) · IDENTIFIED FROM THE TRANSCRIPT · source
“And sell a marketplace and say, Oh, yeah, we've got docs. Go check them out. They didn't like that, right? 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. It's just the value of really good discovery. I often find founders are so in, you know, 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.”
2025-11-30 · Lenny's Podcast · What world-class GTM looks like in 2026 | Jeanne DeWitt Grosser (Vercel, Stripe, Google) · IDENTIFIED FROM THE TRANSCRIPT · source
“I mean, one, I would sort of say. Think the other thing this is straightforward but often not done enough is like a lot of good companies invest in docs you know good thing to do and but they stop there and particularly if you're 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 in with their particular setup a great example of this this is from Stripe was you know Stripe was excellent at marketplaces most you know 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”
2025-11-30 · Lenny's Podcast · What world-class GTM looks like in 2026 | Jeanne DeWitt Grosser (Vercel, Stripe, Google) · IDENTIFIED FROM THE TRANSCRIPT · source
“SEO impacts AEO, and everybody's thinking about AEO right now. And so, you know, 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, you know, 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.”
2025-11-30 · Lenny's Podcast · What world-class GTM looks like in 2026 | Jeanne DeWitt Grosser (Vercel, Stripe, Google) · IDENTIFIED FROM THE TRANSCRIPT · source
“Yeah, another principle we really developed this at SHREPE, and I brought it to Versailles, 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. You know, 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 we're doing at Vercel is great data on the internet that helps people understand the performance of their website and how fast your website is actually impacts SEO and”
2025-11-30 · Lenny's Podcast · What world-class GTM looks like in 2026 | Jeanne DeWitt Grosser (Vercel, Stripe, Google) · IDENTIFIED FROM THE TRANSCRIPT · source
“Because in many cases, they'd never drawn their architecture diagrams. So they left that meeting with an asset and a sense of like, wow, this is a really collaborative person who's like deeply interested in helping me like, you know, 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 you know we try to go map those out and figure out how do you you know bring the product to bear make it really human and and hopefully that creates a customer for life”
2025-11-30 · Lenny's Podcast · What world-class GTM looks like in 2026 | Jeanne DeWitt Grosser (Vercel, Stripe, Google) · IDENTIFIED FROM THE TRANSCRIPT · source
“Companies sales sort of the first call after you're qualified. You know, 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 uncover pain, 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, displaced where value lied. But the customer also learned a lot themselves.”
2025-11-30 · Lenny's Podcast · What world-class GTM looks like in 2026 | Jeanne DeWitt Grosser (Vercel, Stripe, Google) · IDENTIFIED FROM THE TRANSCRIPT · source
“And so, you know, when that happens, when technical differentiation kind of narrows, what are other things that will differentiate you? And, you know, sort of thinking outside of tech, like 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”
2025-11-30 · Lenny's Podcast · What world-class GTM looks like in 2026 | Jeanne DeWitt Grosser (Vercel, Stripe, Google) · IDENTIFIED FROM THE TRANSCRIPT · source
“Yeah, 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 cut up and even longer before Hotmail and others did, right? So that was the level of like 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 have been able to do previously. And so I kind of felt like, huh, like software's starting to commoditize a little bit.”
2025-11-30 · Lenny's Podcast · What world-class GTM looks like in 2026 | Jeanne DeWitt Grosser (Vercel, Stripe, Google) · IDENTIFIED FROM THE TRANSCRIPT · source
“Yes, it is fun to like. 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 Burcell builds Vercelle with Brussel. 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.”
2025-11-30 · Lenny's Podcast · What world-class GTM looks like in 2026 | Jeanne DeWitt Grosser (Vercel, Stripe, Google) · IDENTIFIED FROM THE TRANSCRIPT · source
“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 engine team at Versal can build these agents so easily is because the Versal platform is making it that easy to use our framework to find infrastructure and get that agent onto into production very rapidly.”
2025-11-30 · Lenny's Podcast · What world-class GTM looks like in 2026 | Jeanne DeWitt Grosser (Vercel, Stripe, Google) · IDENTIFIED FROM THE TRANSCRIPT · source
“So 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 Vercel. So you get the AI gateway that lets you call different models. You have a sandbox if you're running on trusted 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 because 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 kind of workflow builders that are somewhere between fully WYSIWYG, almost like drag and drop and a little bit more code.”
2025-11-30 · Lenny's Podcast · What world-class GTM looks like in 2026 | Jeanne DeWitt Grosser (Vercel, Stripe, Google) · IDENTIFIED FROM THE TRANSCRIPT · source
“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.”
2025-11-30 · Lenny's Podcast · What world-class GTM looks like in 2026 | Jeanne DeWitt Grosser (Vercel, Stripe, Google) · IDENTIFIED FROM THE TRANSCRIPT · source
“I 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 sort of because everyone's 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, you know, 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 because most things are getting.”
2025-11-30 · Lenny's Podcast · What world-class GTM looks like in 2026 | Jeanne DeWitt Grosser (Vercel, Stripe, Google) · IDENTIFIED FROM THE TRANSCRIPT · source
“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.”
2025-11-30 · Lenny's Podcast · What world-class GTM looks like in 2026 | Jeanne DeWitt Grosser (Vercel, Stripe, Google) · IDENTIFIED FROM THE TRANSCRIPT · source
“So, 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 $1,000. So that's like a, you know, 90 plus percent reduction in total cost there. And, you know, there are a lot, 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, you know, 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.”
2025-11-30 · Lenny's Podcast · What world-class GTM looks like in 2026 | Jeanne DeWitt Grosser (Vercel, Stripe, Google) · IDENTIFIED FROM THE TRANSCRIPT · source
“Yes. So actually, that's the second half of my answer that I forgot to forgot. That's perfect. Which is sort of like build 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, you know, I mentioned with the lead agent that was a six-week process with one human, a third of his time, that deal bought the lost bot version was like two days. Like basically we riffed on it. He had it 40 hours later. You know, now we're continuing to refine it for the other things I mentioned. And what's also interesting about them is they, you know, for better or worse, for sale, but that lead agent, which runs full stack on Vercelle, will cost us about $1,000 to run for the entire year.”
2025-11-30 · Lenny's Podcast · What world-class GTM looks like in 2026 | Jeanne DeWitt Grosser (Vercel, Stripe, Google) · IDENTIFIED FROM THE TRANSCRIPT · source
“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.”
2025-11-30 · Lenny's Podcast · What world-class GTM looks like in 2026 | Jeanne DeWitt Grosser (Vercel, Stripe, Google) · IDENTIFIED FROM THE TRANSCRIPT · source
“It is. We had a really interesting one of the things we're doing at Russell. So 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.”
2025-11-30 · Lenny's Podcast · What world-class GTM looks like in 2026 | Jeanne DeWitt Grosser (Vercel, Stripe, Google) · IDENTIFIED FROM THE TRANSCRIPT · source
“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 will now run sprints, which is like, those are just bugs. They're bugs near your go-to-market process. So you should not have them. And, you know, 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 org.”
2025-11-30 · Lenny's Podcast · What world-class GTM looks like in 2026 | Jeanne DeWitt Grosser (Vercel, Stripe, Google) · IDENTIFIED FROM THE TRANSCRIPT · source