The future of AI-powered sales with Vercel COO, Jeanne DeWitt
Timestamps are as accurate as they can be but may be slightly off. We encourage you to listen to the full context.
Podcast Summary
In this episode, Lenny sits down with Jeanne DeWitt Grosser, COO at Vercel and former go-to-market leader at Stripe, to explore what sets world-class go-to-market teams apart. (05:26) Grosser defines go-to-market as any function that touches customers or generates revenue, encompassing marketing, sales, customer success, and support. The conversation dives deep into the transformative role of AI in sales processes, with Grosser sharing how her team reduced their SDR function from 10 people to just 1 through AI agents. (19:55) They also discuss the rise of the "go-to-market engineer," a hybrid role that bridges technical expertise with sales process optimization. (10:52)
Speakers
Jeanne DeWitt Grosser
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.
Lenny Rachitsky
Host of Lenny's Podcast and author of Lenny's Newsletter, focused on product management, growth, and startup strategy.
Key Takeaways
AI Agents Can Dramatically Reduce Sales Overhead
Grosser demonstrated how AI can transform sales efficiency by building a lead qualification agent that reduced their SDR team from 10 people to 1 while maintaining the same conversion rates. (19:55) The agent was built by a single GTM engineer in 6 weeks, working only 25-30% of their time, and costs just $1,000 annually to run versus over $1 million in salaries. This freed up 9 SDRs to focus on higher-value outbound activities, showing how AI can elevate rather than replace human sales talent.
Think of Go-to-Market as a Product Experience
Rather than viewing sales as transactional interactions, successful companies design the entire customer journey like a product experience. (47:00) At Stripe, Grosser replaced traditional discovery calls with collaborative whiteboarding sessions where prospects would draw their payment architecture. This gave customers a valuable asset while allowing the sales team to understand their technical setup and competitive landscape, creating a consultative rather than interrogative experience.
The Go-to-Market Engineer is an Emerging Critical Role
The rise of the GTM engineer represents a new hybrid role that brings technical expertise to sales processes. (10:52) These professionals, often former sales engineers with development backgrounds, build AI agents and automate workflows that previously required multiple team members. They force companies to be more rigorous about documenting their sales processes early, as you can't automate what you can't clearly define.
Customer Segmentation Should Drive Company Strategy
Effective segmentation goes beyond simple size categories (SMB, Mid-Market, Enterprise) to include growth potential, business model, and product-specific attributes. (01:00:00) At Vercel, they segment by size, growth rate, traffic volume (using Google's CrUX data), and workload type (e-commerce vs. crypto vs. SaaS). This segmentation framework should be company-wide knowledge, not just a go-to-market tool, as it informs product development, marketing messaging, and sales strategy.
Build Sales Teams That Think Like Product Managers
The best sales organizations serve dual purposes: driving revenue and conducting R&D for the product team. (01:10:03) Grosser's litmus test is that if you put a salesperson in front of 10 engineers, it should take 10 minutes to figure out they're not a product manager. This requires deep product knowledge and the ability to translate customer feedback into actionable product insights rather than just feature requests.
Statistics & Facts
- Jeanne's team reduced their SDR function from 10 people to 1 person using AI agents, while maintaining flat lead-to-opportunity conversion rates. (19:55)
- The AI lead agent costs approximately $1,000 per year to run versus over $1 million in SDR salaries - a 90%+ cost reduction. (43:02)
- 80% of customers buy to avoid pain or reduce risk, as opposed to 20% who buy to increase upside. (58:38)
- Salespeople typically spend only 30-40% of their time actually talking to customers, with the majority spent on research, follow-up, and administrative tasks. (17:44)
