The future of AI-powered sales with Vercel COO, Jeanne DeWitt
Lenny's Podcast: Product | Career | Growth
10 HOURS AGO
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
10 HOURS AGO
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.
GTM strategy is increasingly central to competitive advantage, especially as AI transforms traditional sales functions. The rise of the go-to-market engineer enables automation of repetitive tasks like prospecting and follow-up, allowing human teams to focus on high-value engagement. Companies should hire GTM engineers around the time they have 10 salespeople to codify scalable processes. AI agents are now performing at levels comparable to human SDRs, reducing staffing needs and increasing efficiency. Viewing GTM as a product helps align sales with product development, while segmentation based on technical and behavioral data—not just company size—improves targeting. Sales success often hinges on addressing customer risk avoidance rather than promising upside. Finally, building a sales org that engineers respect requires deep product understanding, feedback integration, and collaboration across teams. Product-led growth has limits, and long-term scale typically demands a hybrid approach including sales.
06:15
06:15
GTM includes all customer-facing and revenue-generating functions
08:43
08:43
Go-to-market teams now act as consultants using AI to bring technology to life for customers
13:00
13:00
An AI agent is being built to replicate human sales workflows and generate fill-in-the-blank email templates.
14:21
14:21
AI will eliminate outbound prospecting
21:19
21:19
AI agent matches human performance in lead conversion with fewer touches
23:48
23:48
SDRs generate pipeline by talking to prospective customers, either inbound or outbound
26:04
26:04
Founders should bring in revenue operations earlier to enable scalable GTM processes
34:33
34:33
DealBot identifies inability to demonstrate value as the core reason for lost deals.
43:38
43:38
Experimental Run Rate Revenue (ERR) enables one-year AI trials before commitment
44:34
44:34
Vercel's sales engineers with CS degrees are building AI agents directly on the platform
46:37
46:37
Thinking about GTM as a product is a powerful framework for product builders.
50:33
50:33
Providing website performance insights to prospects creates immediate value regardless of sale.
58:16
58:16
About 80% of customers buy to avoid pain or reduce risk, not to increase upside.
1:03:39
1:03:39
High-traffic small companies are treated as enterprise due to workload and engagement.
1:09:31
1:09:31
Salespeople need product depth to earn credibility and drive market opportunities.
1:14:00
1:14:00
Most large companies end up with a sales team to sustain growth
1:16:47
1:16:47
Stripe ended its freemium strategy to improve pricing efficiency
1:19:24
1:19:24
Sales comp based on pay-for-performance can limit organizational flexibility