Feb 12, 2025 · 22m · saastr
The Playbook for Going Upmarket with Stripe's CBO and Checkr's COO
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gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions
In this SaaStr presentation, Stripe Chief Business Officer Jeanne DeWitt Grosser and Checkr Chief Operating Officer Lindsay Scrase outline the strategic playbook for scaling B2B SaaS companies into the enterprise market. Drawing on lessons from Stripe and Checkr, they emphasize recognizing true market pull, establishing cross-functional alignment, and enforcing rigorous bottom-up unit economics.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. How this is scored →
Jason as informed peer 2.7 Guest teaching 1.2 Guest disagreement 0.2 Jason pushing back 0.0
speaking balance: gold is Jason, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 4:00 Dismissing board-mandated upmarket expansion
Jeanne dismisses the conventional approach of moving upmarket simply because a board member asked for a larger TAM, calling it an invalid signal.
Hardest push from Jason ▶ 7:13 Pushing past theoretical signals to actual executionJeanne pushes the discussion from recognizing signals to the reality that many companies fail and end up in the graveyard due to poor execution.
Biggest teaching moment ▶ 10:20 Discernment between deal blockers and nice-to-havesLindsay educates on how enterprise roadmap distortion occurs when teams fail to separate true deal blockers from customer nice-to-haves.
Jason holds their own ▶ 18:31 Bottom-up operating models over top-down targetsJeanne demonstrates deep operational command by explaining how a granular hundred-line bottom-up model provides the necessary diagnostic when enterprise metrics deviate.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Jason as informed peer | Guest teaching | Guest disagreement | Jason pushing back | Why |
|---|---|---|---|---|---|---|
| Welcome and Speaker Career Introductions | 2 | 0 | 0 | 0 | Lindsay and Jeanne open the session by introducing each other's career backgrounds across Google, Dialpad, Stripe, and Checkr. The tone is entirely collaborative and collegial with zero conflict. | |
| Identifying Valid Signals and Ideal Customer Profiles | 3 | 2 | 1 | 0 | Jeanne breaks down the critical distinction between real enterprise demand and false signals like an innovation lab pilot ('getting the whale, not the fin'). Lindsay builds on this with Checkr's experience with DoorDash and Lyft. | |
| Checkr's Upmarket Playbook: Focus, Dedication, and Discernment | 2 | 2 | 0 | 0 | Lindsay details Checkr's early missteps attempting to enter enterprise without dedicated engineering capacity, and explains the need for ruthless discernment between deal blockers and nice-to-haves. | |
| Stripe's Upmarket Strategy: Company Alignment and GTM Architecture | 3 | 2 | 0 | 0 | Jeanne explains how Stripe formed a dedicated lighthouse account list and paired respected engineers with sales calls, emphasizing that moving upmarket requires dedicated GTM architecture rather than standard sales hiring formulas. | |
| Adapting Pricing and Packaging for Enterprise Customers | 4 | 1 | 0 | 0 | Both speakers walk through the shift from growth-at-all-costs to efficient unit economics, detailing payback periods, bottoms-up spreadsheets, and unbundling modular pricing models for enterprise buyers. | |
| Key Takeaways and Concluding Remarks | 2 | 0 | 0 | 0 | The speakers wrap up with actionable takeaways focused on rigorous sales unit economics and granular bottoms-up operating models for planning. |
Statements from this episode (15)
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…”
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…”
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.”
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.”
DoorDash was Checkr's first customer, according to COO Lindsay Scrase
“At Checkr, our first customer was DoorDash.”
Checkr paused an early enterprise push due to product and engineering gaps
“Checkr years ago did this wrong. So there were all the signals Jean was mentioning there. Our customers are pulling us up a lot of demand and interests, even like closing some early, you know, more innovative enterprise logos. And the team at the time, before …”
Checkr COO: Never trade away enterprise logo rights
“Make sure your sales teams are not trading away logo rights. You have to get those logos to be able to have them as referenceable customers, and often it takes one big lighthouse logo in an industry, and then the dominoes start to fall, and you start to be abl…”
Google's G Suite product team resisted adding page numbers for years
“I remember, I don't know if you remember this, it took like an act of Congress to get Product to build page numbers into the G Suite portfolio. For years, no, we don't need page numbers. And we just think people don't use those anymore.”
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”
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.”
SaaS sales and marketing spend dropped from 55% in 2019 to 30%
“If you look at SaaS companies, the amount that they're spending on sales and marketing is a percentage of revenue. This was as high as over 50, 55% in 2019. The peak of spend, free money, investment, growth at all costs. That's down to 30% in 2024, just becaus…”
Scrase: Top-quartile SaaS firms have 3x shorter payback and 7x higher valuation
“Also, if you think about payback period, if you look at top quartile SaaS companies versus bottom quartile, top quartile have three X shorter payback period than the bottom quartile and seven X higher valuation.”
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.”