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

Overview

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Highlights

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

Lenny's Podcast: Product | Career | Growth

10 HOURS AGO
Lenny's Podcast: Product | Career | Growth

Lenny's Podcast: Product | Career | Growth

10 HOURS AGO
OverviewShownoteHighlightsTranscriptChaptersPins

Shownote

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 organi...

Highlights

In this episode, Jeanne DeWitt Grosser, a seasoned GTM leader with experience at Stripe, Google, and Vercel, dives into the evolving landscape of go-to-market strategy in the age of AI. She explores how modern sales organizations are being redefined by technology, cross-functional collaboration, and new roles that bridge engineering and revenue teams.
06:15
GTM includes all customer-facing and revenue-generating functions
08:43
Go-to-market teams now act as consultants using AI to bring technology to life for customers
13:00
An AI agent is being built to replicate human sales workflows and generate fill-in-the-blank email templates.
14:21
AI will eliminate outbound prospecting
21:19
AI agent matches human performance in lead conversion with fewer touches
23:48
SDRs generate pipeline by talking to prospective customers, either inbound or outbound
26:04
Founders should bring in revenue operations earlier to enable scalable GTM processes
34:33
DealBot identifies inability to demonstrate value as the core reason for lost deals.
43:38
Experimental Run Rate Revenue (ERR) enables one-year AI trials before commitment
44:34
Vercel's sales engineers with CS degrees are building AI agents directly on the platform
46:37
Thinking about GTM as a product is a powerful framework for product builders.
50:33
Providing website performance insights to prospects creates immediate value regardless of sale.
58:16
About 80% of customers buy to avoid pain or reduce risk, not to increase upside.
1:03:39
High-traffic small companies are treated as enterprise due to workload and engagement.
1:09:31
Salespeople need product depth to earn credibility and drive market opportunities.
1:14:00
Most large companies end up with a sales team to sustain growth
1:16:47
Stripe ended its freemium strategy to improve pricing efficiency
1:19:24
Sales comp based on pay-for-performance can limit organizational flexibility

Chapters

Introduction to Jeanne DeWitt Grosser
00:00
Defining go-to-market
05:26
The evolution of go-to-market roles
08:43
The rise of the go-to-market engineer
11:23
Implementing AI in sales processes
14:21
Optimizing sales with AI agents
15:28
Defining sales roles: SDRs and AEs
23:47
When to hire a GTM engineer
26:04
Hiring and scaling sales teams
29:04
The ideal go-to-market engineer
30:50
The go-to-market tool stack
34:24
Advice on building a great sales bot
40:39
Vercel’s unfair advantage
44:34
Go-to-market as a product
46:37
Innovative sales tactics at Stripe
47:04
Effective go-to-market tactics
52:38
Segmentation strategies
1:00:37
Building a sales org that engineers love
1:09:31
Thoughts on PLG and pricing
1:14:00
Sales compensation and hiring
1:16:44
Lightning round and final thoughts
1:19:24

Transcript

Lenny Rachitsky: I've been getting so many asks for go-to-market help. Jeanne DeWitt Grosser: With AI, it's just intensified. Because you have 10 players pursuing the same market opportunity. And so your ability to actually bring the product to market, to...