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  1. Lenny's Podcast: Product | Career | Growth
  2. The future of AI-powered sales with Vercel COO, Jeanne DeWitt
The future of AI-powered sales with Vercel COO, Jeanne DeWitt

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

Lenny's Podcast: Product | Career | Growth · Nov 30, 2025

Vercel COO Jean Grosser explains how the 'Go-To-Market Engineer' uses AI to 10x sales efficiency and why you should treat GTM as a product.

Vercel's 'Go-to-Market Engineer' Role Combines Sales and Code to Automate Outreach

This emerging role applies engineering and AI to GTM functions, building agents to automate tasks like lead qualification and personalized outreach. This dramatically increases efficiency, allowing one person, with an AI agent, to do the work of ten.

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

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

Lenny's Podcast: Product | Career | Growth·3 months ago

80% of Customers Buy to Reduce Risk, Not to Increase Upside

Startup founders often sell visionary upside, but the majority of customers—especially in enterprise—purchase products to avoid pain or reduce risk (e.g., missing revenue targets). GTM messaging should pivot from the "art of the possible" to risk mitigation to resonate more effectively with buyers.

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

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

Lenny's Podcast: Product | Career | Growth·3 months ago

Design Your Go-to-Market Motion Like a Product to Differentiate

As software commoditizes, the buying experience itself becomes a key differentiator. Map the entire customer journey, from awareness to renewal, and design unique, valuable interactions at each stage. This shifts the focus from transactional selling to creating a memorable, human-centric experience that drives purchasing decisions.

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

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

Lenny's Podcast: Product | Career | Growth·3 months ago

Replace Interrogative Discovery Calls with Collaborative Whiteboarding Sessions

Instead of a typical first sales call that quizzes a prospect, Stripe implemented collaborative whiteboarding sessions. By jointly mapping the prospect's technical architecture, the sales team gathered deep insights while the customer received a valuable asset (their own architecture diagram), establishing a value-add relationship from the start.

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

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

Lenny's Podcast: Product | Career | Growth·3 months ago

Elite Sales Reps Should Be Indistinguishable from Product Managers

Vercel COO Jean Grosser's litmus test for a great salesperson is that engineers shouldn't be able to tell they aren't a PM for at least 10 minutes. This requires deep product knowledge, enabling sales to act as an R&D function by translating customer feedback into valuable product signals.

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

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

Lenny's Podcast: Product | Career | Growth·3 months ago

The Best GTM Engineers Are Former Sales Engineers, Not Traditional SWEs

To build effective GTM automation, hire people who understand both the technology and the sales process. Vercel found success by transitioning its technical sales engineers—who were already former developers—into GTM Engineer roles. This ensures automated workflows are grounded in proven, real-world sales best practices.

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

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

Lenny's Podcast: Product | Career | Growth·3 months ago

Segment Customers by Growth Potential, Not Just Company Size

For consumption-based models, simple size-based segmentation (SMB, Enterprise) is insufficient. Stripe and Vercel use a two-axis model: company size (x-axis) and growth potential (y-axis). A small company growing at 200% YoY is more valuable and warrants more sales investment than a large, stagnant one.

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

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

Lenny's Podcast: Product | Career | Growth·3 months ago

Vercel's AI "DealBot" Uncovers the True Reasons for Lost Deals

Instead of relying on subjective feedback from account executives, Vercel uses an AI agent to analyze all communications (Gong transcripts, emails, Slack) for lost deals. The bot often uncovers the real reasons for losing (e.g., failure to contact the economic buyer) versus the stated reason (e.g., price).

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

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

Lenny's Podcast: Product | Career | Growth·3 months ago

Vercel's AI Lead Agent Does the Work of 9 SDRs for Just $1,000 Annually

By building a custom AI agent for inbound lead qualification, Vercel reduced its inbound SDR team from ten people to one. The agent, which cost only $1,000 per year to run, maintained conversion rates while decreasing response time and number of touches needed.

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

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

Lenny's Podcast: Product | Career | Growth·3 months ago