Jeanne DeWitt Grosser

COO, Vercel · 1 appearance on the record.

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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.

8statements → 5claims → 2claims resolved → 3.88/5average certainty → 1.38/5average debate potential → 1said about them ↓

1 supported 1 partly supported 0 contradicted 3 not checkable as stated how the 5 claims stand · each chip opens the sources

5 assertions · 3 insights · every statement was checked. The predictions and assertions are the 5 claims: statements the public record can support or contradict. 2 are resolved, and 3 name no date, number or outcome precise enough to check. Everything else (opinions, insights, what ifs, disclosures) can never be settled by the record, so it carries no assessment.

The record, in short

What the tape says about how Jeanne argues and how the claims held up. Everything they said, and everything said about them, is in the tabs below.

Their most notable supported claim

Assertion Supported

Stripe Won Amazon.com in Singapore as an Early Enterprise Client

“And then on the other side, we won Amazon's, Amazon.com in Singapore.”

Jeanne DeWitt Grosser Feb 12, 2025 ▶ 5:16 The Playbook for Going Upmarket with Stripe's CBO and Checkr's COO

What they said8 What others said1 Episodes1

Everything Jeanne DeWitt Grosser said on the Official SaaStr Podcast that made the record, most notable first. Filter by type, assessment or year in the ledger →

Insight

Grosser: Startups moving upmarket must secure core enterprise workloads over pilots

“If you go into enterprise, you wanted to get the whale, not the fin. A fin was like our little derogatory term to me, like, you didn't really get a legit workload at that company. So I think a lot of times people will get a side project, an experimental busine…”

Jeanne DeWitt Grosser Feb 12, 2025 ▶ 4:34 The Playbook for Going Upmarket with Stripe's CBO and Checkr's COO

Assertion Not checkable as stated

Stripe had zero sales engineers when Jeanne DeWitt Grosser joined

“When Stripe was selling into developers, believe it or not, when I showed up to run the sales team, we didn't have a single sales engineer or solution architect”

Jeanne DeWitt Grosser Feb 12, 2025 ▶ 12:39 The Playbook for Going Upmarket with Stripe's CBO and Checkr's COO

Insight

Grosser: Enterprises prefer predictable, modular pricing over standard pay-as-you-go models

“Enterprises like predictability. They also like a lot more modularity. They like more all-apart. And so we really had to do a lot to unbundle our pricing for enterprise, let them buy more sub-components, and in some cases, price fundamentally differently.”

Jeanne DeWitt Grosser Feb 12, 2025 ▶ 14:59 The Playbook for Going Upmarket with Stripe's CBO and Checkr's COO

Insight

Grosser: SaaS companies need 100-line bottom-up revenue models for 2025

“If you do not have a hundred line item bottoms up spreadsheet supporting your top down revenue model, I think you will be less effective in 2025 than you would be otherwise.”

Jeanne DeWitt Grosser Feb 12, 2025 ▶ 22:02 The Playbook for Going Upmarket with Stripe's CBO and Checkr's COO

Assertion Partly supported

Stripe's 2017 enterprise push was driven by Shopify, Lyft, and Squarespace

“So for Stripe in that first camp, this was back in 2017 that we started our foray into enterprise, and it was the Shopify's, the Lyft's, Squarespace's were all growing up, bringing in adult CFO's, contemplating IPOs, and so they had a bunch of demands.”

Jeanne DeWitt Grosser Feb 12, 2025 ▶ 4:59 The Playbook for Going Upmarket with Stripe's CBO and Checkr's COO

Assertion Supported

Stripe Won Amazon.com in Singapore as an Early Enterprise Client

“And then on the other side, we won Amazon's, Amazon.com in Singapore.”

Jeanne DeWitt Grosser Feb 12, 2025 ▶ 5:16 The Playbook for Going Upmarket with Stripe's CBO and Checkr's COO

Assertion Not checkable as stated

Grosser: Stripe's first-year enterprise deals were smaller and higher velocity than expected

“In Stripe's case, actually, it turned out that we were doing a lot more deals, but they were smaller and higher velocity in enterprise in year one.”

Jeanne DeWitt Grosser Feb 12, 2025 ▶ 19:43 The Playbook for Going Upmarket with Stripe's CBO and Checkr's COO

Assertion Not checkable as stated

Stripe's enterprise customers buy at least two products on average

“So our enterprise customers on average buy at least two products for Stripe.”

Jeanne DeWitt Grosser Feb 12, 2025 ▶ 20:59 The Playbook for Going Upmarket with Stripe's CBO and Checkr's COO

The other half of the tape: Jeanne DeWitt Grosser's own voice is left out of every number here. 1 statement on the record names them. every mention, with the transcript →

Statements about Jeanne DeWitt Grosser, by other people (1)

Assertion Not checkable as stated

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…”

Lindsey Scrase Feb 12, 2025 ▶ 1:53 The Playbook for Going Upmarket with Stripe's CBO and Checkr's COO

Appearances (1)

Episode	Date	Speaking time
The Playbook for Going Upmarket with Stripe's CBO and Checkr's COO	Feb 12, 2025	10m

Jeanne DeWitt Grosser

The record, in short

Their most notable supported claim

Statements about Jeanne DeWitt Grosser, by other people (1)

Appearances (1)

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