What world-class GTM looks like in 2026 | Jeanne DeWitt Grosser (Vercel, Stripe, Google)
Jeanne DeWitt Grosser built world-class GTM teams at Stripe, Google, and, most recently, Vercel, where she serves as COO and oversees marketing, sales, customer success, revenue operations, and field engineering. She transformed Stripe’s early sales organization from the ground up and advises founders on GTM strategy.
We discuss:
1. Why GTM is becoming more strategically important in the AI era
2. The rise of the GTM engineer
3. A primer on segmentation
4. How to build a sales org that engineers and product teams respect
5. The changing calculus of build vs. buy for go-to-market tools in the AI era
6. Why most customers buy to avoid pain rather than to gain upside
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Brought to you by:
Datadog—Now home to Eppo, the leading experimentation and feature flagging platform: https://www.datadoghq.com/lenny
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Stripe—Helping companies of all sizes grow revenue: https://stripe.com/
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Transcript: https://www.lennysnewsletter.com/p/what-the-best-gtm-teams-do-differently
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My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/179503137/my-biggest-takeaways-from-this-conversation
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Where to find Jeanne DeWitt Grosser:
• X: https://x.com/jdewitt29
• LinkedIn: https://www.linkedin.com/in/jeannedewitt
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Where to find Lenny:
• Newsletter: https://www.lennysnewsletter.com
• X: https://twitter.com/lennysan
• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/
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In this episode, we cover:
(00:00) Introduction to Jeanne DeWitt Grosser
(05:26) Defining go-to-market
(08:43) The evolution of go-to-market roles
(11:23) The rise of the go-to-market engineer
(14:21) Implementing AI in sales processes
(15:28) Optimizing sales with AI agents
(23:47) Defining sales roles: SDRs and AEs
(26:04) When to hire a GTM engineer
(29:04) Hiring and scaling sales teams
(30:50) The ideal go-to-market engineer
(34:24) The go-to-market tool stack
(40:39) Advice on building a great sales bot
(44:34) Vercel’s unfair advantage
(46:37) Go-to-market as a product
(47:04) Innovative sales tactics at Stripe
(52:38) Effective go-to-market tactics
(01:00:37) Segmentation strategies
(01:09:31) Building a sales org that engineers love
(01:14:00) Thoughts on PLG and pricing
(01:16:44) Sales compensation and hiring
(01:19:24) Lightning round and final thoughts
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Referenced:
• Vercel: https://vercel.com
• Stripe: https://stripe.com
• Rosalind Franklin: https://en.wikipedia.org/wiki/Rosalind_Franklin
• Ben Salzman on LinkedIn: https://www.linkedin.com/in/bensalzman
• SDK: https://ai-sdk.dev/docs/introduction
• Gong: https://www.gong.io
• Lyft: https://www.lyft.com
• Instacart: https://www.instacart.com
• DoorDash: https://www.instacart.com
• “Sell the alpha, not the feature”: The enterprise sales playbook for $1M to $10M ARR | Jen Abel: https://www.lennysnewsletter.com/p/the-enterprise-sales-playbook-1m-to-10m-arr
• A step-by-step guide to crafting a sales pitch that wins | April Dunford (author of Obviously Awesome and Sales Pitch): https://www.lennysnewsletter.com/p/a-step-by-step-guide-to-crafting
• Kate Jensen on LinkedIn: https://www.linkedin.com/in/kateearle
• Lessons from scaling Stripe | Claire Hughes Johnson (former COO of Stripe): https://www.lennysnewsletter.com/p/lessons-from-scaling-stripe-tactics
• Atlassian: atlassian.com
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Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.
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Lenny may be an investor in the companies discussed.
To hear more, visit www.lennysnewsletter.com
SaaStr 785: The Playbook for Going Upmarket with Stripe's CBO, Jeanne Dewitt Grosser, and Checkr's COO, Lindsey Scrase
SaaStr 785: The Playbook for Going Upmarket with Stripe's CBO, Jeanne Dewitt Grosser, and Checkr's COO, Lindsey Scrase
Want to know when to move upmarket and how to actually pull it off? Jeanne Dewitt Grosser, Chief Business Officer at Stripe, and Lindsey Scrase, COO at Checkr, have done it multiple times at companies like Google Cloud, Stripe, and Checkr.
They came to SaaStr Annual to share what they've learned about making the move to go more enterprise actually work. They dive into their professional histories, strategies for startups when targeting and pivoting to enterprise markets, and the signals to watch for before making the leap. Learn from their experiences, including the importance of an aligned company push, the evolution of pricing, and tips for managing unit economics efficiently.
Don't miss their actionable advice on understanding unit economics and building a solid operating model to enhance your business success.
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Hey everybody - thanks to the 10,000 of you who came out to SaaStr Annual. We had a blast and big news -- we'll be back in MAY of 2025. That's right, the SaaStr Annual will be a bit earlier next year, May 13-15 2025. We'll still be back in the same venue, in the SF bay area at the 40+ acre sprawling san mateo county events center. Grab your tickets at saastrannual.com with code JASON50 for an extra discount on our very best pricing.
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20 Sales: The Stripe Sales Playbook; Who Should Create It, When Should it Be Done, Where Do Many Go Wrong | How To Identify 10x Sales Hires and How To Structure the Hiring Process in Sales with Jeanne DeWitt Grosser, Head of Americas Revenue & Growth @ St
Jeanne DeWitt Grosser is Head of Americas Revenue & Growth @ Stripe. In this role, Jeanne is responsible for all sales functions across the region including Sales Development, AEs, Solutions Architects, and many more. Jeanne also continues to spearhead Stripe's Enterprise strategy. Prior to this role, Jeanne was Stripe's Head of North America Sales where she built out Stripe's Acquisition Sales teams. Pre-Stripe, Jeanne was CRO @ Dialpad and also spent many years at Google in numerous different roles including most recently as Director of GSuite SMB & Mid-Market Sales, North America and LATAM.
In Today's Episode with Jeanne DeWitt Grosser You Will Learn:
1.) Entry into Sales:
How did Jeanne make her way into her first sales job in tech?
What did Jeanne learn from her many years at Google about how sales should interact with engineering?
In hindsight, what would Jeanne have done differently/improved from her time with Dialpad?
How did the role with Stripe come about?
2.) The Playbook:
Does the founder need to be the one to create the sales playbook?
When is the right time to bring in the first sales hire? Should they be a sales leader or rep?
How does both the playbook and the type of sales hire change when hiring for a product-led-growth motion vs a traditional enterprise motion?
What are the single biggest mistakes founders make when hiring their first in sales?
3.) The Hiring Process:
How should founders structure the hiring process for their first sales hires?
What did Dialpad do in the sales hiring process that worked well? How has Jeanne taken that to her hiring process at Stripe?
What should be achieved or learned in each consecutive interview?
How can founders use sales case studies most effectively? How can founders know if sales candidates truly have a strong grasp of the product?
What are early signs of a 10x sales hire? What are red flags to look out for in the process?
4.) Sales Onboarding:
What does the ideal onboarding process look like for new sales hires?
What tasks and duties should all sales hires perform in the first 60 days?
What are early signs that a new hire is not performing to the right standard?
How does the first few months differ for sales reps when comparing a product-led-growth company to an enterprise company?
What should sales leaders do to ensure that new hires engage with product and customer success efficiently?