When PLG works and its limits

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.