Jeanne DeWitt Grosser
COO, Vercel. On 4 shows, 4 appearances, plus 1 compilation re-air not counted. The Shows tab opens the full record on each.
executiveoperator@jdewitt29 ↗LinkedIn ↗vercel.com ↗
Jeanne DeWitt Grosser serves as the Chief Operating Officer at Vercel. Previously, she spent over seven years scaling commercial organizations at Stripe as Head of Americas Revenue & Growth and Chief Business Officer, following sales leadership roles at Google and Dialpad.
4shows
4appearances
98statements
7resolved
5supported
0contradicted
71%fully supported
4said about them ↓ Everything Jeanne DeWitt Grosser said on any show that made the record, most notable first. Each card names its show and opens the statement there.
Vercel replaced a $1M SDR team with a $1,000 AI agent
“That lead agent, which runs full stack on Purcell, will cost us about a thousand dollars to run for the entire year. 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 perspecti…”
Grosser: The 17 hyper-specialized GTM roles are going to collapse
“So we've gone through a period of like hyper specialization and go to market you know, depending on how you count them, there are, you know, I think somebody quoted like 17 different, ah, roles within go to market these days. And I hypothesize that a lot of th…”
Grosser: Pure product-led growth stops working beyond Series B
“So at Stripe, as an example, product-led growth, sort of like the online self-search channel was awesome for, let's call it a series A, series B company. The minute you get past that, it doesn't work anymore. You're not like, if you build it, they will come. P…”
Grosser: Great founder brand marketing alone cannot build a predictable revenue engine
“A lot of founders, Guillermo's a good example, John and Patrick were examples of this well, are like excellent brand marketers, but that does not a predictable revenue engine make on its own.”
Grosser: Vercel deployed AI lead qualification agents matching human SDR performance
“I launched a GTM engineering team in the first six weeks on the job at Vercel. So basically, we took Three sales engineers were like, congrats, you're now founding members of our GTM Eng team, where we're gonna go bring agents to bear across everything in GTM.…”
Grosser: Stripe executives donated headcount across P&Ls to self-solve budgets
“Stripe got much, much, much more rigorous about the budget is the budget, like, the, we've got headcount OpEx, and, like, that will be the number that we have collectively as a company. And across the course of the year, opportunities would emerge that you wou…”
Grosser: John Collison said cross-functional colleagues she doubts are "dead to her"
“He said, within your own organization, you do a great job of being both demanding and supportive. Cross-functionally, when you don't think somebody's good at their job, they're dead to you.”
Grosser: AI agents could double salespeople's customer-facing time to 70%
“And I think we're getting to a point where With layering in agents, ideally, we finally get salespeople to a point where they're actually spending 70% of their time interacting with humans, and we can get the research, the follow-up, the things that are a litt…”
Vercel: AI lead agent matched human conversion rate with fewer touches
“What we were able to do is Hold that lead to opportunity conversion rate flat so the agent is as good as our humans were, but it's actually condensed the number of touches it takes to convert Because it's so much quicker at responding relative to leads inevita…”
Grosser: Average SDRs Are Capable of Starting Directly in Closing Roles
“But I think the average SDR Could have gone straight into outbound or straight into an S&P closing role. And so basically what we're just doing is shifting folks into something that uses more of their full capacity right out of the gates, rather than sort of t…”
AI analysis revealed Vercel's biggest lost deal wasn't actually about price
“So the biggest loss that quarter, according to the account executive, was lost on price. And when you ran the agent over every Slack interaction, every email, every gone call, it said, actually you lost because you never really got in touch with the economic b…”
Grosser: Company context makes bespoke internal AI agents superior to vendor software
“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.”
Grosser: The sales experience becomes the primary differentiator when software commoditizes
“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.”
DeWitt Grosser: Annual sales comp plans make organizations less flexible
“I struggle with sales comp because you know, 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.”
Grosser: Great sales reps can run effective calls without deep product knowledge
“A savvy salesperson can talk to somebody actually knowing very little about the product they're selling because what great salespeople do is ask good questions. And so if you can teach folks what questions to ask out of the gates, they actually can run calls p…”
Grosser: Product managers pitch effectively because they own the product vision
“Products should be pretty darn good at pitching as well. It has a stronger point of view often on the vision because it's in their head.”
Grosser: Modern sales compensation structures are outdated 20-year-old relics
“I just think a lot of it is still a relic of how sales worked 20 years ago, and I think there's, like, a huge opportunity to be more innovative in the metrics, in the integration of cash and equity.”
Grosser: Stripe's internal tooling and systems haven't scaled with sales headcount
“Honestly, like, we're hyper growth, and I think our, the underlying tool systems operations haven't scaled as quickly as we've Scaled salespeople. Data, rigor, velocity, those all hold us back.”
Grosser: Transitioning to second-line manager is one of leadership's biggest leaps
“I think actually one of the biggest leaps in leadership to make is going from a frontline manager to a second line manager. So there, you gotta learn to delegate and get comfortable with that, but you're gonna, you know, seven direct reports on average, like, …”
Grosser: Direct reports should independently mirror the executive's decisions 90% of the time
“If I've done a good job of helping you understand my mental model, then nine times out of 10, you should be able to ask Ask yourself that question and come up with the answer I would have come up with had I been there alongside you.”
Grosser: Early enterprise wins lead product to blame sales and sales to blame gaps
“If you work in product and engineering, that suggests in your mind, well, if one enterprise brought it, surely all of them can, right? And so this must be a go-to-market problem of, like, you're not doing a good enough job of bringing forth the value of our pr…”
Grosser: COO role is whatever crucial functions founders choose not to manage
“I often think COO is sort of like the set of functions that a founder knows are incredibly important and doesn't personally want to manage at this particular moment in time.”
Grosser: Laying out real problems in first interview tests candidate motivation
“Mostly telling you these are the problems that, this is the reason I'm hiring your role. I have the following issues that you will need to come and resolve. And I find that by putting those things out on the table in the first meeting, basically, you get a sen…”
Grosser: Strong executive candidates teach interviewers new mental models early on
“Typically, I have learned something. I have learned multiple things. Yes. You know, often, Early, like, you know, that second meeting, they already are giving me a mental model I didn't have. They're talking to me either about a thing they did where I can imme…”
The other half of the tape: Jeanne DeWitt Grosser's own voice is left out of every number here. Other people bring the name up 3 times in 1 episode across the shows. 1 statement on the record names them. every mention, with the transcript →
Who brings them up most Lenny Rachitsky 3
Statements about Jeanne DeWitt Grosser, by other people (1)
Stripe had 10 salespeople when Jeanne DeWitt Grosser joined in 2016
“There were, what, 10? 10 salespeople when she joined. She scaled it to hundreds and hundreds of sellers, built out many functions from scratch, including SDRs, customer success, solutions engineering, architects, and now Jean is the chief business officer at S…”
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Lenny's Podcast 3
One line per show, most statements first. The link opens Jeanne's full record on that show: the calibration, argument clarity, speaking style and every statement made there.
| Show | Role there | Eps | Statements | Record | |
|---|---|---|---|---|---|
| LENNY'S PODCASTLEDGER | COO, Vercel | 1 | 38 | 100% 1/1 | full record on Lenny's Podcast → |
 20VCLEDGER | COO, Vercel | 1 +1 | 32 | 0% 0/1 | full record on 20VC → |
 IN DEPTHLEDGER | COO, Vercel | 1 | 20 | 100% 3/3 | full record on In Depth → |
 SAASTRLEDGER | COO, Vercel | 1 | 8 | 50% 1/2 | full record on the Official SaaStr Podcast → |