Lenny's Podcast: Product | Career | Growth

chevron_right

The future of AI-powered sales with Vercel COO, Jeanne DeWitt

whatshot 688 snips

Nov 30, 2025

Guest

Jeanne DeWitt Grosser

Jeanne DeWitt Grosser, COO of Vercel and former leader at Stripe and Google, shares insights into the evolving landscape of go-to-market strategies in the AI era. She discusses the emergence of GTM engineers and their role in automating sales workflows. The conversation touches on customer behavior, emphasizing that buyers often seek to minimize risks. Jeanne also advises on the importance of aligning sales with product development, and how segmentation can guide effective outreach while fostering collaboration across teams.

01:26:02

forum

Ask episode

web_stories

AI Snips

view_agenda

Chapters

menu_book

Books

auto_awesome

Transcript

info_circle

Episode notes

00:00 / 00:00

GTM Is Now A Strategic Differentiator

AI has intensified go-to-market importance because many players chase the same opportunity.
Differentiation in GTM now determines who wins when product differences narrow.

00:00 / 00:00

Project Rosalind: Mapping Every Company

At Stripe Jeanne built Project Rosalind: a company-universe to personalize outreach.
It failed in 2017 but the idea resurfaces now because AI makes it feasible.

00:00 / 00:00

Shadow Top Sellers Before Building Agents

Shadow your top performers to codify human workflows before automating them.
Then translate those workflows into agents that replicate the best human actions.

Get the Snipd Podcast app to discover more snips from this episode

Defining go-to-market and scope

05:29 • 2min

chevron_right

How GTM roles have evolved recently

07:54 • 4min

chevron_right

The rise and role of the GTM engineer

11:28 • 3min

chevron_right

What GTM engineers automate first

14:22 • 4min

chevron_right

Agents boosting SDR productivity

18:18 • 4min

chevron_right

Will AI replace SDRs?

21:57 • 2min

chevron_right

SDR vs AE roles explained

24:02 • 2min

chevron_right

When to hire a GTM engineer

26:18 • 3min

chevron_right

Hiring your first salesperson timing

29:05 • 2min

chevron_right

Ideal GTM engineer profile

30:57 • 2min

chevron_right

Building agents on Vercel's platform

32:42 • 2min

chevron_right

Using Gong and DealBot to surface insights

34:34 • 4min

chevron_right

Agent-driven go-to-market iteration

39:00 • 2min

chevron_right

Build vs buy for internal agents

40:46 • 2min

chevron_right

Agent platforms and procurement challenges

43:10 • 2min

chevron_right

Vercel tooling advantage for GTM Eng

44:50 • 2min

chevron_right

Go-to-market as a product experience

46:45 • 4min

chevron_right

Tactics: deliver value at every touchpoint

50:44 • 2min

chevron_right

Sales discovery and listening skills

52:45 • 3min

chevron_right

Using unique insights to win attention

55:57 • 2min

chevron_right

Framing sales as risk-reduction

57:55 • 3min

chevron_right

Segmentation primer and framework

01:00:45 • 4min

chevron_right

Practical segmentation and company alignment

01:05:04 • 4min

chevron_right

Making sales a partner to product

01:09:32 • 4min

chevron_right

When PLG works and its limits

01:14:01 • 3min

chevron_right

Pricing as a product decision

01:16:53 • 3min

chevron_right

Sales comp and hiring hot takes

01:19:29 • 3min

chevron_right

Final thoughts and leadership lessons

• Mentioned in 25 episodes

Obviously Awesome

How to Nail Product Positioning so Customers Get It, Buy It, Love It

April Dunford

In 'Obviously Awesome,' April Dunford provides a practical, step-by-step guide on product positioning. Drawing from her extensive experience in tech marketing, Dunford explains how to identify a product's 'secret sauce' and sell it to the right audience. The book covers key topics such as the five components of effective positioning, how to connect an audience to the product's value, choosing the best market, and leveraging market trends. It is punctuated with witty anecdotes and compelling case studies, making it both entertaining and illuminating for entrepreneurs, marketers, and salespeople.

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/

—

Transcript: https://www.lennysnewsletter.com/p/what-the-best-gtm-teams-do-differently

—

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:

• X: https://x.com/jdewitt29

• LinkedIn: https://www.linkedin.com/in/jeannedewitt

—

Where to find Lenny:

• Newsletter: https://www.lennysnewsletter.com

• X: https://twitter.com/lennysan

• 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

• 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

—

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.

To hear more, visit www.lennysnewsletter.com

Home Top podcasts Popular guests Top books