GTM 175: Why Most Go-To-Market Motions Collapse at Scale

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Why do so many go-to-market motions fall apart right when a company starts to scale?

In this episode of the GTMnow Podcast, Sophie Buonassisi sits down with Jeanne DeWitt Grosser, former GTM leader at Google and Stripe and now COO at Vercel, to unpack why GTM fragility is one of the most underdiagnosed risks in startups and scaling companies.

This is a deep, operator-level conversation about what actually breaks in sales, why AI won’t magically fix it, and how the best teams treat go-to-market like a product that must be designed, tested, and iterated.

If you are a founder, operator, or investor navigating growth, this episode will give you clearer mental models for building GTM that actually holds up under pressure.

Discussed in this episode

Why most GTM motions fail at scale, even with strong products
What it really means to treat go-to-market like a product
How AI changes execution without changing fundamentals
The rise of the forward deployed engineer
Why “lost on price” is usually a lie
What great sales reps still do better than anyone in the AI era
How to think about joining companies “early” without getting timing wrong

Listen if GTM feels fragile, unpredictable, or overly dependent on heroes.

Episode highlights

00:00 – Introduction

01:00 – “Yes is great. No is great. Maybe will kill you.”

02:00 – Why go-to-market should be treated like a product

04:45 – Designing the experience of being sold to

06:30 – Using AI to debug GTM process failures

09:00 – Why “lost on price” usually isn’t about price

12:00 – What go-to-market engineering actually is

16:00 – The rise of the forward deployed engineer

20:45 – AI, agents, and what still needs human judgment

25:45 – What great sales reps do differently in the AI era

29:30 – Why GTM roles are becoming more consultative

33:30 – Will there be an AI reckoning?

38:00 – What “joining early” really means

42:00 – Career lessons from Google, Stripe, and Vercel

44:00 – Closing thoughts

Key takeaways

1. Go-to-market should be treated like a product.
Product teams prototype, storyboard, and obsess over user experience. Most GTM teams do none of that. But being sold to is an experience. If you don’t design it intentionally, you’re still creating one, just accidentally.

2. Sales motions fail because they’re rarely choreographed.
The strongest GTM teams think in sequences. What experience tees up the next one? When should a whiteboard replace a deck? When does ROI come in? This is product thinking applied to human systems.

3. AI only helps after you decide what “good” looks like.
Agents are most effective in deterministic environments. If you can’t articulate your best practices, AI will only scale inconsistency. Clarity first, automation second.

4. Most “lost on price” deals aren’t actually about price.
When Jeanne dug into losses, the real issues were things like missing the economic buyer or failing to quantify ROI. Those are process bugs, not rep failures. Treating GTM like a product lets you debug those bugs systematically.

5. The forward deployed engineer exists because buyers are overwhelmed.
Customers often know something needs to change but don’t know what to solve first. The people who win bring structure, frameworks, and pattern recognition into ambiguity. That consulting-oriented motion is becoming core, not optional.

6. Great sales reps aren’t going away in the AI era.
If anything, trust and navigation matter more when decisions feel riskier. The best reps understand an organization’s decision-making better than the organization itself. AI may compress workflows, but judgment remains human.

7. “Early” is about trajectory (not headcount).
Jeanne joined Google, Stripe, and Vercel later than most people think. What mattered wasn’t what number she was joining the company, but rather about the company’s growth trajectory. If you’re worried you’re too late, is it ever too late if the ceiling for growth is high enough?

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GTM 175 Episode Transcript

Sophie Buonassisi: Jean, welcome to GTM now.

00:00:18:07 – 00:00:19:10

Jeanne DeWitt Grosser: Thank you for having me.

00:00:19:14 – 00:00:41:12

Sophie Buonassisi:

Absolutely. It’s a pleasure to be here. Great to be in the new office. Congratulations on the state. It’s it’s fantastic. And I appreciate it. Yeah. Yeah. And we’ll dive into the details. But before we dive into the details, let you just take a bit of a zoomed out view because you’ve now run a market of some incredible companies like Google and had you scaled stripe for nearly a decade.

00:00:41:12 – 00:00:51:02

Sophie Buonassisi:

And now obviously, if you could give operators and founders listing just one piece of go to market advice, what would it be?

00:00:51:04 – 00:01:11:20

Jeanne DeWitt Grosser:

Oh. It’s tough to narrow down to what I will use. One that I literally said, about an hour ago, which is, yes. Is are great. No’s are great. Maybe they’ll kill you. I think, salespeople earlier in their career, founders sometimes, don’t want to get to that clarity because you are afraid you will get it.

00:01:11:20 – 00:01:29:17

Jeanne DeWitt Grosser:

No, but the no no is actually, like the best thing you can possibly get, because either it will enable you to not waste your time anymore or figure out how you would go concretely overcome that. So I always encourage people to try to get to that level of clarity.

00:01:29:19 – 00:01:31:13

Sophie Buonassisi:

Efficiency. It sounds like there was a data.

00:01:31:15 – 00:01:34:01

Jeanne DeWitt Grosser:

Leviathan and talking to me. Yeah.

00:01:34:01 – 00:01:54:05

Sophie Buonassisi:

Exactly. And the fortunate part is we’re going to dive into a lot more piece of advice. We don’t have to keep it at one. But it’s really interesting to hear, especially someone with your incredible experience from multiple different businesses, what that one piece is because it comes from a common thread across all. So super interesting. Now something I’ve heard you say is go to market should be treated as a product.

00:01:54:05 – 00:02:06:12

Sophie Buonassisi:

Yep. And in this age of AI, that’s incredibly important. And but it’s also changing. Curious what does that mean? What does trading go to market like a product mean? In the age of AI?

00:02:06:14 – 00:02:33:02

Jeanne DeWitt Grosser:

So I started seeing this at at stripe. And, but I think it is that much more important during the age of AI and the, the point of it really is that when you are building a product, you are extremely thoughtful about the experience that you were trying to create for the person using that, you know, you prototype 5 or 10 different variants of the same screen.

00:02:33:04 – 00:03:00:12

Jeanne DeWitt Grosser:

You think about whether it should have ten additional pixels here or not. You know, you, wireframe all of the different ways in which, folks are going to work their way through that product. And, I didn’t feel that many companies did that from a, sales perspective. But I would argue, just like you’re trying to create an experience in utilizing your product, you’re trying to create an experience and being sold to you.

00:03:00:12 – 00:03:22:08

Jeanne DeWitt Grosser:

Just have it with humans who, you know, for better or for worse or slightly, harder to control than software. Yeah. So so the idea was, that you’re creating something choreographed and you’re actually thinking about how do you do an experience that tease up the next experience that you want to have with that person or other people?

00:03:22:10 – 00:03:53:07

Jeanne DeWitt Grosser:

And that you could actually storyboard that the way you would storyboard experiences in a product and then figure out, do you bring that to life via, a pitch deck, a demo, a whiteboarding session, and on say, you know, etc., etc. where I think that that becomes that much more relevant in the AI era is when you bring agents to bear agents, at least right now, in my view, are most successful when they’re doing something somewhat deterministic.

00:03:53:09 – 00:04:13:00

Jeanne DeWitt Grosser:

And so in order to get an agent to do parts of your go to market, you actually have to have a point of view on what excellence looks like. And then an agent often can replicate that, in certain scenarios. So, so putting the energy into what is best practice, you know, what is the outcome that you want?

00:04:13:00 – 00:04:18:20

Jeanne DeWitt Grosser:

How would you get there? TS you up for that? And being able to bring AI to bear on that.

00:04:18:22 – 00:04:38:05

Sophie Buonassisi:

That completely makes sense. And you’re speaking the same language that we love and preach to. I think what we see all the time, and it’s always been slide number two of our deck at GTM fund is first time founders focus on product, second time founders focus on distribution. And that’s a huge price to market. Yeah. It’s like how how do you create that roadmap.

00:04:38:05 – 00:04:48:17

Sophie Buonassisi:

And then how do you iterate upon it? I’m curious because that’s one area that we see a lot of roadblocks on. Okay. You make an initial roadmap. What does the iteration process look like if you treat it like a product?

00:04:48:20 – 00:04:52:00

Jeanne DeWitt Grosser:

This is where I’ve been actually most geeking out.

00:04:52:00 – 00:04:52:12

Sophie Buonassisi:

On using.

00:04:52:12 – 00:05:10:19

Jeanne DeWitt Grosser:

So challenges that you have and go to market are one actually adherence to the process. So if you took the time to be like here are the stages a deal goes through in this stage, you should be talking to these people. You should be doing these activities, achieving these exact criteria. Likelihood that everybody actually does that is not ultimately that high.

00:05:10:21 – 00:05:33:19

Jeanne DeWitt Grosser:

And, and then how do you get signal noise on where you really need to iterate, on aspects of your, your sales process? Typically, you know, you try to draw those things out and forecast calls, deal reviews, and then having your product marketers go and talk to your best sellers, shadow of them, etc.. But now actually, there’s a lot you can do to systematically get those insights.

00:05:33:21 – 00:05:59:13

Jeanne DeWitt Grosser:

So examples of that are we use gong very heavily. Now that much more, because we are building agents that actually then track, all of those conversations and we’re not quite here yet, but we think we will get to a point where we can determine the degree to which people are actually adhering to what we think is best practice.

00:05:59:15 – 00:06:23:09

Jeanne DeWitt Grosser:

And being able to see actually when people hear, do they perform better? Because if, if they don’t, probably our best practice is not, in fact, not but then also more rapidly get insights. So a great example of this is every sales organization you do, you know, a loss loss deal review some cadence.

00:06:23:11 – 00:06:42:04

Jeanne DeWitt Grosser:

And typically you’re reliant on a single field, maybe a field tree within Salesforce, which requires that reps actually use it. It requires that they pick the thing from the pick list that maps to the thing you wanted them to pick, so on and so forth. And that they actually totally understand why they didn’t fact lose that deal.

00:06:42:07 – 00:07:09:07

Jeanne DeWitt Grosser:

Right. So one of the first agents we built was, a lost bot, which would basically go read every email, read every slack interaction. We’re very heavy slack users with customers, listen to every gong call and be able to say, here’s why I think you really lost. When we used we train the agent to use a meet and pick rubric, sort of use some of the the aspects of our sales process under, underpinning that.

00:07:09:09 – 00:07:31:07

Jeanne DeWitt Grosser:

And so that helps you then figure out as an example, you know, we had lost, on price, on one deal, but when you ran the agent across all those interactions, it actually said you didn’t talk to an economic buyer, and you did not do a great job of providing a well quantified TCO analysis. And those are on me as a leader that’s actually not on the rep.

00:07:31:09 – 00:07:58:04

Jeanne DeWitt Grosser:

So we realized that was actually a gap in our sales process, was where we equipping people to go and access an economic buyer or, you know, a developer oriented company. You got to actually teach people how to do executive selling. And then, you know, did we have an easy to execute ROI, TCO type template? So that was that was sort of a bug there that, you know, we can then use to more rapidly close those gaps in our process.

00:07:58:06 – 00:08:09:00

Sophie Buonassisi:

Make sense. Super interesting use case to. Yeah. And how does it differ from stripe now traversal on how you treat your go to market like a product and iterate upon it. Are they different or similar?

00:08:09:01 – 00:08:30:02

Jeanne DeWitt Grosser:

There’s a lot of similarities that I carried across. Like we were very focused on being experiential at, at stripe. And so and thinking about, hey, people want an experience of being sold to, you’re helping. One of the things that’s been true of a lot of the things I’ve sold is, I like to sell things that are mission critical.

00:08:30:04 – 00:08:56:17

Jeanne DeWitt Grosser:

So taking people’s money, right, mission critical, you know, providing the underlying infrastructure that gets our product onto the internet, mission critical. Yeah. And so those are high risk decisions. And so at stripe, again, very experiential complex product. Also same things here at Vercel. The big difference, at Vercel is actually how we use the product to sell the product.

00:08:56:19 – 00:09:22:17

Jeanne DeWitt Grosser:

So v0 is our vibe coding application. And you know, we now frequently, you know, our, our ROI pricing tool is actually now a V0 that people will go and, you know, revive code, customize it to that particular, customer. Or we have a deck, that actually is in V0 rather than Google Slides.

00:09:22:17 – 00:09:40:04

Jeanne DeWitt Grosser:

But again, you can go do or actually a lot of what we’re doing right now is, hey, we’ll go build an agent together. So we’ll do a workshop. And by the end of it, you will have built an agent that emulates, say, some of the things I might talk about, you know, in our conversation today.

00:09:40:05 – 00:09:54:08

Jeanne DeWitt Grosser:

So it’s more just kind of, vercel is a motto of vercel builds for Sal with for Sal, which is basically. Yeah, like it’s the ultimate dog fooding company. And we try to do the exact same thing, with and go to market.

00:09:54:13 – 00:10:14:16

Sophie Buonassisi:

Very, very cool. And you mentioned for your roadmap and how you, how you actually document your go to market. You mentioned a couple of things. You mentioned whiteboarding slides. Where have you is there a specific format that you think resonates best for leaders or works best, or you’d recommend for anyone looking to create greater documentation?

00:10:14:18 – 00:10:39:04

Jeanne DeWitt Grosser:

Well, I don’t know that I have like a singular format, although I will say that I also think documentation is, more important than ever. As folks think about EO, you know, and actually feeding an agent, you know, a, context. So I stripe definitely taught me hard core documentation, and I feel like I’m carry that forward.

00:10:39:04 – 00:11:03:21

Jeanne DeWitt Grosser:

And now it’s not just you do it because it’s the company’s culture. It’s more you do it actually, because it will produce better AI results. So for for the other ones, to me it’s more what is the most efficient and effective way to get someone to the moment? So I’ll, I’ll, I’ll give you an early stripe example on that.

00:11:03:23 – 00:11:28:04

Jeanne DeWitt Grosser:

We when you would start selling when sold up market for the first time, people basically would tell you that they were not in pain. And we’re like, I know that you are, because I’ve sort of seen, you know, similar customers. So one of the things that we did there was we figured out that doing a whiteboarding session where you would get them to help you draw their architecture on a.

00:11:28:04 – 00:11:28:20

Sophie Buonassisi:

Whiteboard.

00:11:29:01 – 00:11:50:07

Jeanne DeWitt Grosser:

Was actually a great way to get someone to an moment. And behind the scenes, we called it this Frankenstein tech stack, where you had 12 things under the hood to do. What could be done? Soup to nuts with stripe. And so we were trying to use that as a way to get an moment of like, oh wow, you would like, get rid of that vendor, get rid of that vendor.

00:11:50:09 – 00:11:57:10

Jeanne DeWitt Grosser:

You know, reduce costs over here, increase performance over there. And that was way more effective than me taking you through 25 slides.

00:11:57:11 – 00:12:19:00

Sophie Buonassisi:

Yeah, that totally makes sense. It sounds like whatever is going to be most effective for both working with customers and iterating as a as a team, executive leadership team internally. Yeah. Very cool. Yeah. And one of the things that you’ve kind of pioneered under the go to market strategy is go to market engineering. Yeah, we’re going to start at stripe before it became a little bit more popularized, which it is now.

00:12:19:00 – 00:12:30:08

Sophie Buonassisi:

And correct me if I’m wrong, but I believe you actually hired for that role first at Vercel within maybe your first six weeks. Yeah. Of joining. Why are you so bullish on go to market engineering?

00:12:30:10 – 00:12:54:14

Jeanne DeWitt Grosser:

I’ve always felt that go to market was under like I didn’t have actually the technology it needed. I have been for a while, sort of like bearish on a decent amount of the GTM tech stack. Yeah. Like people would always come to me, you know, VCs, angel investors. I’m like, okay, you work in GTM, obviously you would want to invest in this thing.

00:12:54:15 – 00:13:15:02

Jeanne DeWitt Grosser:

And, it’s sort of driven me crazy the bulk of my career because I find the GTM or the. Yeah, GTM stack to kind of be this Venn diagram of, like, you’ve got to buy ten things, each of them provide ten things, four of which overlap with the ten things the next thing provides. And then then you like stitch them together and it it’s it’s not great.

00:13:15:04 – 00:13:47:20

Jeanne DeWitt Grosser:

But you never had a real the cost of building your own software was too high. So the closest you ever got to that was like a Salesforce admin. You know, and, now you get to this age and basically the marginal cost of producing software is going close to zero, with the ability to vibe code, to have platforms like for sales at cloud that just make that development and getting that agent or those pixels onto the internet, even if that’s your internal intranet.

00:13:47:22 – 00:14:04:12

Jeanne DeWitt Grosser:

Super easy. And so for me, it was, that’s actually one of the things I talked about with gear before I joined the company was I want to build a really different go to market. And so I’m going to want to do things that other people don’t find, like, will you be excited about that? What?

00:14:04:12 – 00:14:20:03

Jeanne DeWitt Grosser:

She was, and so coming in, I wanted to be just customer zero of everything. And I felt like we could make the go to market or meaningfully more efficient and effective and again, build this, go to market like a product,

00:14:20:05 – 00:14:31:11

Sophie Buonassisi:

Super interesting. What do you think are the biggest differentiators from that conversation? You have a demo. What are the biggest things that you’re doing different and go to market then? Yeah, we.

00:14:31:13 – 00:14:51:09

Jeanne DeWitt Grosser:

I mean, I’ll answer this two ways. So one is the ability to be customer zero is really compelling. So we saw sort of the the business for Vercel up until this point was being this front end cloud. So a lot of folks host their marketing site on Vercel. Well, we have a working site for Vercel. Right.

00:14:51:11 – 00:15:10:19

Jeanne DeWitt Grosser:

So how do we try to build that into something world class in a way that then makes the product, that much better? Like, I would argue our design team is one of the more demanding customers of Vercel, and in doing so, we build something better for everybody else. Same thing with the go to market engineering team.

00:15:10:21 – 00:15:33:14

Jeanne DeWitt Grosser:

You know, we were the earliest adopter of the AI cloud. And so, AI gateway, is is one of those products that helps you connect to multiple models. You know, we started using that workflows. We released a couple months ago. This lets you build more complex agent orchestration. Similarly, will point out all the rough edges before anybody else, gets to it.

00:15:33:16 – 00:16:02:14

Jeanne DeWitt Grosser:

So, so one, I think it’s kept GTM and EPD connectivity really tight because we’re an active contributor of feedback into the product. To it results in us getting to know the product and the art of the possible of what it can do that much better, which makes us more effective at bringing it to market. And then three, because Vercel intends to be 99th percentile in our own internal use of AI.

00:16:02:16 – 00:16:10:09

Jeanne DeWitt Grosser:

You know, we’re sort of pushing where is every possible place that you can think of adding an agent, you know, to the process.

00:16:10:11 – 00:16:21:22

Sophie Buonassisi:

Yeah. Incredible. Incredible. That makes sense. And how are you leveraging go to market engineering in Vercel? Like, are there any tactical examples you can share of how you deployed that role?

00:16:22:00 – 00:16:53:02

Jeanne DeWitt Grosser:

Yeah. So I’ll probably bucket in a couple of ways. So way one is building agents. Yeah. So with that, what we’ve been doing is to basically start with the most deterministic roles and effectively have a go to market engineer, shadow your best person, work with managers, work with others. Where you need to make the process more legible is what we call it, like codify really what that best practices.

00:16:53:04 – 00:17:18:17

Jeanne DeWitt Grosser:

So, we started with an inbound inbound qualification, which is one of the more straightforward things to do, and built an agent around that. We’ve then turned that into what we call internally a playbook platform, which is now starting to get into outbound, where what it’s doing is basically running plays. But again, if if the play itself is, kind of like you can make them relatively micro.

00:17:18:17 – 00:17:42:00

Jeanne DeWitt Grosser:

So that’s not trying to boil an outbound motion, but much more. If a company has these technical and thermographic attributes, then run this type of play. Here’s the content. Here is how you customize it. And ostensibly, we can get to a point where we’re running 100 of these simultaneously and just feeding new companies that fit those attributes. So that’s another one.

00:17:42:02 – 00:18:01:19

Jeanne DeWitt Grosser:

Third area was around install base. So when you’re trying to do renewals or expand customers, you’ve got a lot of your own internal data to bear that helps you understand what else they could buy, how they could get a lot more value. So we’ve been able to condense a lot of the prep work around that.

00:18:01:21 – 00:18:31:20

Jeanne DeWitt Grosser:

So that’s sort of the, the, the first bucket where, can you either augment or replace certain types of, work done by humans with an agent? Then, the second area that that we have is, is more on sort of vibe coding, but then production izing that. So, you know, every single account executive, sales engineer, sales development, rap, in my work is using B0 on a daily basis.

00:18:31:22 – 00:18:52:20

Jeanne DeWitt Grosser:

Which is great, that we do hackathon GTM hackathons where they’re coming up with stuff. Yeah. Versal. Every single Friday at 8 a.m., does, company wide, demo day. And, that’s not just the engineers who contribute that the, you know, we’ll have the GTM teams show up, finance shows up, legal shows up, with each of the things they’re doing within their function.

00:18:52:20 – 00:19:10:08

Jeanne DeWitt Grosser:

But, anyway, so second bucket is sort of unleash the creativity of your org. There are a lot of folks within my organization who are not GTM engineers, like, they don’t have computer science degrees, you know, advanced code coding skills, but they come up with some really good stuff.

00:19:10:11 – 00:19:11:16

Sophie Buonassisi:

Yeah.

00:19:11:18 – 00:19:26:06

Jeanne DeWitt Grosser:

And so then you just, harness that creativity and we’ll take the best of the best and then hand that over to go to market engineering, to really productize that, so, I think it was two weeks ago. We had some.

00:19:26:06 – 00:19:26:21

Sophie Buonassisi:

Really.

00:19:26:21 – 00:19:48:05

Jeanne DeWitt Grosser:

Really good. How do you, basically make a more dynamic, website based quote instead of like, here’s your PDF of, like, you know, your plain text, here are the SKUs you’re buying and how much they cost. This is much more, interactive. You can play with it. You can understand associated ROI, all that type of stuff. So is killer.

00:19:48:07 – 00:20:25:13

Jeanne DeWitt Grosser:

Well, I had a couple rough edges. We’ll hand that over to GTM and to make that truly beautiful. And then we’ll go and we’ll now enable 100 people to use that and use it similarly. And then we actually tracks within GTM engineering. We run it like you would run a product. So we’ll actually look at, okay, what are, you know, may use or, you know, daily use, are people actually using the thing that we said, so, so that’s, that’s sort of the second bucket, and then the third bucket is in line with kind of what I, was talking about previously, which is more like insights.

00:20:25:14 – 00:20:54:01

Jeanne DeWitt Grosser:

So I talked about the last spot. Another amazing thing we built, this was a collaboration with our, our data science team is, we have an agent called D0. Okay. So it’s like a little riff on V0, for data, but, so you can go and query it pretty complex. Questions that you would typically send to a GTM analyst, and use that to get insights about plays we might run.

00:20:54:01 – 00:21:08:06

Jeanne DeWitt Grosser:

You know, what else we might do? So that’s one example. I talked about. Yeah. How we get lost, lost insights, how we, improve our sales process. But that’s sort of the insights bucket.

00:21:08:07 – 00:21:14:15

Sophie Buonassisi:

That’s fascinating. Where do you think that GTM engineering and that kind of iterative function is going.

00:21:14:17 – 00:21:42:15

Jeanne DeWitt Grosser:

Yeah I mean I think a lot about this I haven’t come to a conclusion yet. There’s a world where it is sort of the future of Rub ops, because it does dovetail very closely with your systems and tools team and your data, and operational teams. So right now, how we’ve delineated it is basically your sort of traditional systems team that would sit in rev ops is all about third party software.

00:21:42:17 – 00:22:18:03

Jeanne DeWitt Grosser:

And go to market engineering is much more about first party software. That that we’re building on, on sales cloud. And then right now you’ve sort of got the analytical portion of rev ops contributing. Plus we have a pretty heavy investment for so on on the data science front, but it’s rarely the case that anything that we’re building and go to market engineering isn’t relying on a very well architected data where data lake with the like super thoughtful semantic layer etc..

00:22:18:03 – 00:22:27:21

Jeanne DeWitt Grosser:

And so there’s a lot of stuff that like, I think our GTM team and our agents can do, because actually all the building blocks were there to put them together into an agent.

00:22:27:23 – 00:22:52:04

Sophie Buonassisi:

So you’ve got incredible alignment around the entire team beyond go to market through these kind of demo days, like you mentioned, just overall culture. How do you actually foster that kind of alignment? Because what I’ve heard from multiple different sources is, you know, you are incredible at creating and cultivating alignment between different functions like go to market like product, but you’re doing that like at a macro scale, but you’re also doing that at a micro scale.

00:22:52:05 – 00:22:53:09

Sophie Buonassisi:

So yeah, like.

00:22:53:11 – 00:23:14:17

Jeanne DeWitt Grosser:

Yeah, I, I mean a couple of ways I think like one, I’m just deeply in the weeds on this stuff. Like I geek out on it. So I mean, drew, who runs go to market engineering for me like that for guys getting pinged like, you know, with the frequency that G pings, our product work. Yeah. So, so, so I think that’s like, one is like, you got to live the transformation.

00:23:14:17 – 00:23:34:21

Jeanne DeWitt Grosser:

You want to see and understand the realities of bringing that to life. To those like, I think we tried within go to market to make it highly inclusive and exciting, which is, you know, my view is most of us do a lot of work every day that we didn’t actually want to do. And potentially you aren’t going to have to do it anymore.

00:23:34:23 – 00:24:07:01

Jeanne DeWitt Grosser:

So I think that’s that’s sort of one the framing of like the goal here is actually just to move us all up. Like Maslow’s hierarchy of needs to be more self-actualized. And that again, anyone can participate in this because great ideas are going to come from anywhere. In, in the AI era. And then lastly is just figuring out, you know, that that linkage across the company of customer zero, you know, be demanding, give feedback.

00:24:07:03 – 00:24:33:09

Jeanne DeWitt Grosser:

But I also think, like our engineering team loves it when they’re getting to see the technology that they’ve built showcased. Right. So, like a great example of this was my entire career getting structured feedback associated with revenue into product engineering has been hard. You know, you always try, you get a staggering get, you know, what’s what’s going to help with retention, more revenue, etc..

00:24:33:09 – 00:25:03:07

Jeanne DeWitt Grosser:

Like, I’ve never I’ve tried to build that process numerous times. I’ve never felt I did it perfectly. We built, a GTM feedback app here that sort of takes it out of Salesforce, therefore gives us a ton more flexibility, but it integrates really deeply with Salesforce, with slack, and we now use it as the basis of running, our, EPD, GTM fusion meeting, which is basically where we meet to discuss places where we’re blocked on roadmap items for specific deals.

00:25:03:08 – 00:25:04:19

Sophie Buonassisi:

What’s the frequency of that meeting.

00:25:04:19 – 00:25:26:05

Jeanne DeWitt Grosser:

That that is weekly. We had it, about 90 minutes ago. So, so basically all of our EPD leads and go to market leads and we’ll go through, you know, here’s, here’s where winning, here’s where we’re losing. Here are the top largest open deals, where we’re blocked on some functionality piece of roadmap that we would need to choose to, pull forward.

00:25:26:07 – 00:25:35:22

Jeanne DeWitt Grosser:

Plus, also reviewing the more consolidated GTM feedback of, okay, 30 people have all said, you know, we need to do x, y, z.

00:25:36:00 – 00:25:52:12

Sophie Buonassisi:

I love it. I love it now. Incredible. Appreciate the detail. And then from a function perspective, we talked and spent a lot of time on go to market engineering now left to flip over more to sales. Yes, I’ve heard you express some really interesting views in terms of how a sales role should actually be kind of broken down.

00:25:52:12 – 00:26:13:06

Sophie Buonassisi:

And your Maslow’s hierarchy of needs is fantastic. I feel like we’re all just striving to go to market actualization now, but, what does that sales process look like? Like where are the the best sales reps that you’re seeing, that you’re deploying these go to market engineers to spending their time? And what does that look like as we move forward and genetically.

00:26:13:08 – 00:26:26:09

Jeanne DeWitt Grosser:

So I think that the best sales reps part of that job is not changing at all. And if anything becomes more important, which is best? Sales reps build relationship reps that are high trust and they navigate organizations.

00:26:26:13 – 00:26:27:02

Sophie Buonassisi:

Yeah.

00:26:27:04 – 00:26:51:10

Jeanne DeWitt Grosser:

Where I have really seen sales come to life is when actually a sales rep knows more about an organization than the organization does itself. I remember I won’t I won’t use the name of the company, but this is at stripe, where, it was a large global company. So they had somewhat distributed decision making. And, I was down in Mexico talking to the, you know, leader.

00:26:51:11 – 00:27:14:03

Jeanne DeWitt Grosser:

And in that region, we also had a big footprint with them in the US. And they were both like, we we actually knew how that process was going to get run to make a decision. And, different leaders, because of their newness didn’t. But anyway, that that type of scenario comes up, pretty frequently. So I don’t think that changes at all.

00:27:14:05 – 00:27:35:19

Jeanne DeWitt Grosser:

If anything, I think it becomes much more important because decisions feel riskier right now when it’s not obvious whether you’ve picked the thing that’s going to exist three years from now. And be a market leader, or you’re going to go get 100 people using a thing that fizzles out, and now you got to go change them to something else nine months later.

00:27:35:21 – 00:28:02:23

Jeanne DeWitt Grosser:

So I think that part really stays. I think right now we’re a little bit in like blank check AI mode. Yeah. So our are like, quantifying, cause skills, maybe getting a little lax. But that is going to change for sure when folks are kind of like, okay, now, but at this with this type of AI, etc., etc. for this many months, am I actually getting the ROI I was looking for?

00:28:03:01 – 00:28:54:13

Jeanne DeWitt Grosser:

So I think the salespeople and the companies who get, crisp, fast are at identifying the true value they’re creating or more likely to, go from IRR to IRR, which we can get into. And then I do think you see a lot more of this rise of the forward deployed engineer, which is a lot more around both art of the art of the possible and best practices, where I do think there’s value in that more consulting oriented problem solver, a persona right now, because, a lot of times companies are now showing up knowing I should solve some problems, but I’m not sure which one to solve first.

00:28:54:13 – 00:29:11:21

Jeanne DeWitt Grosser:

How to solve that, how to make a decision about that. And so I actually do think the folks that can bring structure and frameworks to bear, as well as have pattern recognition to be able to bring best practice before it’s potentially codified, are more likely to get deals done quickly.

00:29:11:22 – 00:29:22:12

Sophie Buonassisi:

That makes sense. That makes sense. And for deployed engineers that do, one of the most in-demand roles that we’re hearing from our side on the venture, ones from startups all the way through to more mature companies to.

00:29:22:17 – 00:29:46:16

Jeanne DeWitt Grosser:

Yeah, I mean, when you look at it, it’s sort of like rebranded professional services that we now aren’t consistently charging for and are pulling forward in the sales cycle. But it I mean, it goes to like a lot of companies add in professional services pretty darn late. Right. Like that typically was like a pretty mature go to market motion when you’re doing massive transformation in large companies.

00:29:46:18 – 00:29:55:02

Jeanne DeWitt Grosser:

And the reality is that it’s just more necessary, at this point, again, when folks don’t know what the answer is.

00:29:55:04 – 00:30:18:22

Sophie Buonassisi:

And you mentioned IRR and R and IRR for anyone unfamiliar is experimental. Right, right. Randy. Yeah. Little bit of a jumble there. Yeah. But how are you thinking about that as you are leading an AI infrastructure company. And we know that a lot of people are in these experimental stages. Yep. How are you thinking about your revenue from that perspective?

00:30:19:02 – 00:30:43:19

Jeanne DeWitt Grosser:

Yeah. This is one of the we actually were talking about this yesterday. We had, executive offsite and were, you know, talking about, FY 27 strategy. We started in February. And this is one of those things where I find myself having to remind myself to be very first principled, because I’ve, you know, got this, you know, extensive operating background.

00:30:43:19 – 00:31:09:16

Jeanne DeWitt Grosser:

And you, you know, you learn all the right metrics and LTV. And how do you, you know, think about leading indicators and all the things you want to do to build an investable model. Basically. And now you’re in this moment where you’re having to discern how much of that is still highly relevant. And like at some point the other shoe will drop in some capacity on this current, like, aggressive, AI growth.

00:31:09:21 – 00:31:52:16

Jeanne DeWitt Grosser:

So how much of that rigor is actually like, useful? And if I apply it, I will find myself ahead of the curve at that later date. Versus how much of that might be making one to conservative. And, you know, we should go back into like, the hypergrowth mode. Probably the answer is somewhere in between. And so I just, I sort of find, like, I think it is neither wise to, like, throw the baby out with the bathwater nor to, to, kind of ignore the fact that at the end of the day, like, panels are going to have to make sense.

00:31:52:18 – 00:32:03:02

Jeanne DeWitt Grosser:

And so, like, you just need to have a point of view on the glide path towards a rational PNL, and, you know, when I figure out exactly what that should look like.

00:32:03:02 – 00:32:09:20

Sophie Buonassisi:

Happy to tell you. Well, as I sit down here again. Yeah. Do you think that we’ll have a reckoning, a big reckoning?

00:32:09:22 – 00:32:36:15

Jeanne DeWitt Grosser:

I think we will have some version of one. Mostly because a lot of the market is hyper fragmented. And so you cannot support as many players in the same space as I think we have. Or I’ve hypothesized, that that’s true. You could also argue that, like, AI is going to make markets so much larger that where markets typically might have sustained three players, they actually can have five.

00:32:36:17 – 00:32:58:08

Jeanne DeWitt Grosser:

I’m not sure I totally buy that. So I think you have a lot of companies right now that are somewhere between a feature and a product. At some point they will have to become actual companies. That is one of the sort of, this old, article at this point. But, I think it was McKinsey, a long time ago.

00:32:58:08 – 00:33:16:00

Jeanne DeWitt Grosser:

Had this, like, grow fast or die slow, thing, which I don’t know that that’s the right framing today, but the net of it was okay, a bunch of companies could not figure out how to go from act one, to act two, which is sort of, you know, getting into a new product line, a new segment or a new geo.

00:33:16:02 – 00:33:32:10

Jeanne DeWitt Grosser:

You’re seeing some of these AI companies do some of those things from the outset. But anyway, I have a hard time believing that, there’s not some level of consolidation. But I’m not sure I have a strong hypothesis about how that plays out.

00:33:32:12 – 00:33:45:12

Sophie Buonassisi:

Time will tell. Yes. Well, I’d say to see how you adjust, especially being at the helm of, of a cutting edge AI company. Now you are at Vercel. Yeah. As of, you know, coming up on, coming up on

00:33:45:14 – 00:33:47:20

Jeanne DeWitt Grosser:

What am I getting towards almost at over nine months.

00:33:47:23 – 00:34:16:02

Sophie Buonassisi:

Yeah, yeah. Crazy time flies. But you also spent essentially a decade at Google, a decade at, stripe. Yeah, I think a decade at stripe. You you’re very intentional about how you pick your company, understanding and how you write and go to market, essentially everything that you do. Yeah. Picking the right company to dedicate your career and life to building is one of the most challenging things, especially now with so many different companies.

00:34:16:04 – 00:34:21:11

Sophie Buonassisi:

Yeah, and an abundance of selection. How do you pick your companies?

00:34:21:13 – 00:34:25:04

Jeanne DeWitt Grosser:

Yeah, I, I would say I got lucky on Google.

00:34:25:06 – 00:34:26:14

Sophie Buonassisi:

Yeah.

00:34:26:16 – 00:35:04:04

Jeanne DeWitt Grosser:

And, after I left. So when I left, I think I had clarity on why I was leaving. What I did not think to do at the time was get clarity on why I stayed, and that I then after I left, got that and I boiled it down to three things. And those were basically one, it had extremely well articulated values that were sort of naturally, fundamentally aligned with my own and truly used as decision making frameworks to was extremely large market with natural adjacencies.

00:35:04:06 – 00:35:39:11

Jeanne DeWitt Grosser:

And then three was I mean, Google hired PhD engineers. So they, they were on the inventor side of the software engineering spectrum, which, I was a point when I was, interviewing, leading them straight away, I sort of felt like, the, the average, like, software engineering was starting to commoditize, so, so that that those were the things I look for that led me to stripe, and they then ended up being the things I looked for in coming to Vercel.

00:35:39:13 – 00:36:07:00

Jeanne DeWitt Grosser:

So, similarly, super strong values like, you can’t get through a meeting without saying, they’re deeply embedded and onboarding in how we evaluate candidates, how we do performance reviews every single. We had our company all hands this morning. They are the framework for the agenda for the all hands. It’s just truly pervasive. And then, large market with horizontal margin market with natural adjacencies.

00:36:07:01 – 00:36:34:15

Jeanne DeWitt Grosser:

This is actually, I think some one of the hardest ones to get right, because founders are exceptional at pitching you on. You know why they’re playing and like $1 quadrillion market. But I started to for me realize that, I wanted to look for large horizontal platforms, that those tended to be more large market and to have natural adjacencies.

00:36:34:15 – 00:37:02:01

Jeanne DeWitt Grosser:

So stripe started with credit cards pretty early, got into fraud, got into subscription building. Versus sort of same thing started with front end applications, got into and, and security was getting into AI when I was starting to have conversations. And so I could already see where, it was not going to have a hard time figuring out act two and then resell, probably that much more than, than many companies.

00:37:02:03 – 00:37:44:04

Jeanne DeWitt Grosser:

I spoke to really does employ inventors, right? Like you’ve got this extremely strong open source software, foundation for the company. We frequently acquire founders, and we, we look for, failed founders, active founders, etc., in our interview process as well. So I sort of felt in this, this era in particular where like literally cloud code is now writing at all, I want that and I want to work with the engineers that are going to invent the things that the models are then going to incorporate that, you know, a billion future developers will go use.

00:37:44:06 – 00:38:06:14

Sophie Buonassisi:

Yeah, definitely. I mean make sense. And you, you you spent I mean decades at both companies and you joined early. Yeah. I’m curious for your perspective for anyone looking at early stage companies or maybe thinking that a company that they’re joining might be a little bit too late. Yeah. Curious your perspective there. Yeah.

00:38:06:14 – 00:38:34:17

Jeanne DeWitt Grosser:

This really I it’s changed for me. So I have always in having gotten lucky to work at Google and that was truly a generational company. I, I realized like I only want to work at 99.9 percentile companies in my career. Because I think the problems they solve or more interesting, the people they attract, are, more compelling to work with.

00:38:34:19 – 00:39:10:23

Jeanne DeWitt Grosser:

And, so I joined Google, 2000 employees, which would sound super late. That was in 2004 when I left. And 14, I had been there longer than 99 point something percent of the current employee base stripe. Similarly, I joined 400 employees, multi-billion dollar valuation, and most people have been like, that’s late. Again, when I left nine years later, I’d been there longer than 99.6% of the current employees.

00:39:11:01 – 00:39:33:17

Jeanne DeWitt Grosser:

And so I joined at, something just shy of 600. So actually later than and stripe was, and I, I sure hope I wind up being here longer than 99 point whatever percent of employees or maybe actually, I’d make the argument. The goal would be to be more like 99, 98, because you’d love it if a lot of those early employees stick around, alongside you.

00:39:33:21 – 00:39:42:04

Sophie Buonassisi:

True, true, definitely. You can help cultivate that culture. Bring them there. Well, we’ll sit down at that point in time. Perfect. Yeah. I rewind and hindsight.

00:39:42:05 – 00:40:00:21

Jeanne DeWitt Grosser:

Yeah, we have a joke, actually, at Vercel that we only want to employ 1024, employees. So that might make it hard to get to 99th percentile, because we figure out how to bend the, the curve on, on, you know, a productivity in line with sort of the what’s what you’re seeing more broadly in the AI market right now.

00:40:00:21 – 00:40:17:10

Sophie Buonassisi:

So we can count agents, I guess, for the purposes that’s probably actually going to happen. Yeah. There you go. Yeah, I love it. Well, this has been fantastic. Dean I have a couple last questions for you. Awesome. I’m curious, where do you get your learning back? Are there any books that have been particularly impactful in your career?

00:40:17:12 – 00:40:40:16

Jeanne DeWitt Grosser:

I, I so one that really stuck with me, early days was was crossing the chasm. I’ve like reference that numerous times actually. I interned in business school at Cisco, which at the time was like preeminent enterprise software company. I went there specifically to try to learn, okay, how to how does enterprise get done? And they had I think it is Jeffrey Moore.

00:40:40:16 – 00:41:07:06

Jeanne DeWitt Grosser:

That’s the offer. Like he was actually like an in-house advisor. And they had like a whole Crossing the Chasm methodology. It was really interesting. I think this will be interesting because like, if you look at the technology adoption lifecycle curve, I don’t imagine that that’s the shape of it in the AI era, actually. You know, I read predictable revenues, sort of all the sales books from kind of the Salesforce era of selling, I would say.

00:41:07:06 – 00:41:08:07

Sophie Buonassisi:

Yeah.

00:41:08:09 – 00:41:19:23

Jeanne DeWitt Grosser:

And then more recently, it’s been, you know, I, I want to build something that would be worth writing a book about. So, I mean, also having kids means I read a little.

00:41:19:23 – 00:41:21:18

Sophie Buonassisi:

Less.

00:41:21:20 – 00:41:23:00

Jeanne DeWitt Grosser:

But, no.

00:41:23:00 – 00:41:24:17

Sophie Buonassisi:

I don’t have to be business books we can go beyond.

00:41:24:18 – 00:41:37:00

Jeanne DeWitt Grosser:

Yeah. But, I also just more being, like, part of different operator and hero communities. I think it’s, you know, been interesting to actually just, like, actively debate things and get multiple perspectives at once.

00:41:37:02 – 00:41:53:16

Sophie Buonassisi:

Well, especially now with AI too, when everybody suddenly level set to the same stage of learning. Yeah. For, for arguably one of the first times in humanity. Yeah. Totally. Very cool. And are there any kind of words you live by or kind of words of inspiration. Quote to inspiration for you?

00:41:53:21 – 00:42:12:21

Jeanne DeWitt Grosser:

Oh man. I have a bunch that I have a working with Gene doc that everybody gets when they start. And a number of them are from my mom. And I didn’t realize, like, how often I said them until I left Google. And actually, people wrote me notes and a lot of them referenced that there.

00:42:12:21 – 00:42:30:16

Jeanne DeWitt Grosser:

And then I realize I’m a pretty good one. I mean, I’ll make sure I keep saying it. So, one of the things my mom always said, it was when the going gets tough, the tough get going. So that’s a big one for me. I just sort of choose to always be the optimist and lean in on things.

00:42:30:16 – 00:42:49:23

Jeanne DeWitt Grosser:

And I think it’s particularly relevant. And sales, where there’s no such thing as being a sales leader and not having a quarter where you were behind, where you lost a deal, you know, any of those scenarios. So I think being able to frame things to the positive and feel motivated by that, you know, has always, worked for me.

00:42:50:01 – 00:43:01:23

Jeanne DeWitt Grosser:

And then, stripe, I got known for when I left to go to market. Org folks actually wrote a bunch of Gene isms on a wine bottle for me.

00:43:02:01 – 00:43:03:13

Sophie Buonassisi:

And.

00:43:03:15 – 00:43:15:14

Jeanne DeWitt Grosser:

And one of them, which I didn’t realize I said this much was, I’m pretty sure that deal is not going close on a Saturday. Which is basically a Salesforce hygiene comment, which I think I’ve said more than once ever sell as well.

00:43:15:14 – 00:43:26:09

Sophie Buonassisi:

Yeah. We’re we’re by. Yes. Yeah, sure. A lot of organizations could benefit from that. Yes. Very cool. Super helpful. And where can people find you follow along your journey?

00:43:26:11 – 00:43:38:04

Jeanne DeWitt Grosser:

Mostly on LinkedIn. So, I’m, I would say still my maiden name, so just do it. But I’m pretty sure you can also just do search.

00:43:38:06 – 00:43:47:15

Sophie Buonassisi:

Yeah. Perfect. Well, appreciate the time. Has been fantastic. Really enjoyed the conversation. Yeah. And I look forward to sitting down once we get to that 1024 employee. Absolutely.

00:43:47:15 – 00:43:50:04

Jeanne DeWitt Grosser:

Yes. Well, thanks a lot for having me. A lot of a lot of fun.

00:43:50:08 – 00:44:03:09

Sophie Buonassisi:

You bet. Awesome. Good stuff. Yeah. Is there anything? I just want to be cognizant of your time here. I know we’re one minute over. Yep. Is there anything that we didn’t cover that you’d like to cover? I know we didn’t dive into enterprise. That’s fine, but.

00:44:03:09 – 00:44:03:17

Jeanne DeWitt Grosser:

Yeah.

00:44:03:19 – 00:44:05:09

Sophie Buonassisi:

Oh, good. Warehouse. Great.

00:44:05:09 – 00:44:06:04

Jeanne DeWitt Grosser:

Supernatural.

00:44:06:07 – 00:44:16:09

Sophie Buonassisi:

Yeah. So. Yeah. Look. Fantastic. Yeah. Appreciate it, appreciate it. You really, really wonderful. And, I mean, we’ll get in touch with all the details. Yeah. But overall let me know if ever week. Yeah.

00:44:16:11 – 00:44:19:18

Jeanne DeWitt Grosser:

Awesome. Hope it hopefully that was like gears man who was talking in the background.

00:44:19:18 – 00:44:23:15

Sophie Buonassisi:

At what point hopefully can fix that one in post. Again.

00:44:23:17 – 00:44:24:13

Jeanne DeWitt Grosser:

Yeah okay.

00:44:24:14 – 00:44:25:23

Sophie Buonassisi:

Cool.

00:44:26:01 – 00:44:27:10

Jeanne DeWitt Grosser:

Awesome. Well thanks a lot.

00:44:27:10 – 00:44:30:10

Sophie Buonassisi:

Really appreciate it. Yes. The holidays with the fam. Yeah. You too.

00:44:30:10 – 00:44:32:21

Jeanne DeWitt Grosser:

And likewise, thanks for setting everything up. I’m sure it’ll be excellent.

00:44:33:00 – 00:44:33:15

Sophie Buonassisi:

Yeah.

00:44:33:17 – 00:44:38:02

Jeanne DeWitt Grosser:

And I will leave you with Marie to make sure everybody gets out. And I got to run to my next meeting.

00:44:38:02 – 00:44:41:02

Sophie Buonassisi:

Yes. Good luck on it. All right. See you. We’re in good hands with Marie.

00:44:41:02 – 00:44:42:19

Jeanne DeWitt Grosser:

Yes. She is amazing.

00:44:42:19 – 00:44:47:00

Sophie Buonassisi:

Yeah.

00:44:47:02 – 00:44:48:01

Sophie Buonassisi:

Thank you.

00:44:48:03 – 00:44:51:22

Jeanne DeWitt Grosser:

Okay. Okay. Perfect.

00:44:51:23 – 00:44:57:10

Sophie Buonassisi:

That was wonderful. Yeah. I appreciate your help setting. That’s getting us. Oh, yeah. All good.

Sophie Buonassisi

Sophie Buonassisi is the SVP of Marketing at media company GTMnow and its venture firm, GTMfund. She oversees all aspects of media, marketing, and community engagement. Sophie leads the GTMnow editorial team, producing content exploring the behind the scenes on the go-to-market strategies responsible for companies’ growth. GTMnow highlights the strategies, along with the stories from the top 1% of GTM executives, VCs, and founders behind the strategies and companies.