Assertion Supported AI assessment confidence: 95% certainty 4/5 debate potential 1/5

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

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

Stripe CBO Jeanne DeWitt Grosser discusses early enterprise validation signals at Stripe.

0:00 / 0:05exact quote · 5.1s
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“And then on the other side, we won Amazon's, Amazon.com in Singapore.”

quote is from the automated transcript, cleaned for reading: filler sounds and stutters are removed, nothing is rephrased. names can be misheard (the analysis reads context, assessments check outside sources). how →

More from Jeanne DeWitt Grosser

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
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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
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Jeanne DeWitt Grosser Feb 12, 2025 ▶ 14:59 The Playbook for Going Upmarket with Stripe's CBO and Checkr's COO
Insight
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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 Not checkable as stated
Grosser: Stripe's first-year enterprise deals were smaller and higher velocity than expected
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Jeanne DeWitt Grosser Feb 12, 2025 ▶ 19:43 The Playbook for Going Upmarket with Stripe's CBO and Checkr's COO
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