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

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

Lovable—Build apps by simply chatting with AI

Stripe—Helping companies of all sizes grow revenue

Where to find Jeanne DeWitt Grosser:

• X: https://x.com/jdewitt29

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

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 [email protected].

Lenny may be an investor in the companies discussed.


My biggest takeaways from this conversation:

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