What World-Class GTM Looks Like in 2026
•November 30, 2025
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Why It Matters
As AI intensifies market saturation, companies that embed GTM engineers and AI‑driven, product‑style GTM processes will secure faster, risk‑focused customer acquisition and sustain growth in an increasingly competitive landscape.
Summary
The video explores what a world‑class go‑to‑market (GTM) organization will look like in 2026, emphasizing how AI has amplified competition and made differentiation a strategic imperative. Host Lenny Rachitsky brings on Jean Grosser, former Stripe chief product officer and current COO of Vercel, to dissect the evolving GTM landscape and the emerging roles that enable companies to win at scale.
Grosser reframes GTM as any function that touches a customer or moves a dollar, encompassing marketing, sales, sales engineering, customer success, support, and partnerships. She argues that the traditional siloed approach is giving way to an integrated lifecycle, with hyper‑specialized roles collapsing into broader, product‑like processes. Central to this shift is the rise of the GTM engineer—a technically skilled professional who builds data‑driven, AI‑augmented workflows that automate outreach, personalize messaging, and accelerate the sales cycle.
Key examples illustrate the transformation. Grosser recounts Stripe’s 2017 “Project Rosalind,” a massive company‑universe database that attempted to generate fill‑in‑the‑blank outreach emails; the effort faltered without AI but is now being revived at Vercel with modern AI tools, delivering ten‑fold speed gains. She also cites the insight that “80% of customers buy to avoid pain,” prompting GTM teams to focus on risk mitigation rather than aspirational messaging, and shares a litmus test: an account executive should be indistinguishable from a product manager to a group of engineers within ten minutes.
The implications are clear: firms that treat GTM as a product, embed technical sales talent, and leverage AI‑powered GTM engineers will outpace competitors, especially in crowded AI markets. Start‑ups can achieve rapid go‑to‑market execution without hiring costly senior talent, while enterprises can reduce churn and accelerate revenue by delivering differentiated, risk‑focused buying experiences.
Original Description
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
Brought to you by:
Datadog—Now home to Eppo, the leading experimentation and feature flagging platform: https://www.datadoghq.com/lenny
Lovable—Build apps by simply chatting with AI: https://lovable.dev/
Stripe—Helping companies of all sizes grow revenue: https://stripe.com/
My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/179503137/my-biggest-takeaways-from-this-conversation
Where to find Jeanne DeWitt Grosser:
• LinkedIn: https://www.linkedin.com/in/jeannedewitt
Where to find Lenny:
• Newsletter: https://www.lennysnewsletter.com
• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/
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
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
• 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
_Production and marketing by https://penname.co/._
_For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com._
Lenny may be an investor in the companies discussed.
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