Lenny’s Podcast: Product | Career | Growth

Episode: The Future of AI-Powered Sales with Vercel COO, Jeanne DeWitt
Date: November 30, 2025
Host: Lenny Rachitsky
Guest: Jeanne DeWitt Grosser, COO at Vercel

Episode Overview

This episode dives deep into the rapidly shifting world of AI-powered sales and go-to-market (GTM) strategy with Jeanne DeWitt Grosser, COO at Vercel and former Chief Product Officer at Stripe. Jeanne shares her experiences building world-class GTM teams, the emergence and impact of AI and the new "GTM engineer" role, actionable sales tactics, insights into segmentation, pricing, and what it takes to build sales organizations that partner effectively with engineering and product teams.

Jeanne offers concrete frameworks, stories from Stripe and Vercel, and a future-facing look at how AI is transforming every stage of the customer journey—from lead qualification to deal closing. This episode is an expert's guide for anyone building, leading, or evolving a modern sales organization.

Key Discussion Points & Insights

1. The Evolving Definition of Go-to-Market

Timestamps: [05:50]–[08:44]

• Traditional vs. Modern View:
  GTM used to be just marketing and sales at the “tip of the spear.” Jeanne defines it more holistically: “Any function that touches the customer or makes a dollar—marketing, sales, technical sales roles (SEs, platform architects), customer success, support, partnerships.”
• Integration Across Functions:
  "Those functions often have this Venn diagram strategy... what you're going to want to see more in this particular moment is that that become a really integrated life cycle."
• Role Specialization to Collapse:
  The 17+ hyper-specialized GTM roles will “start to collapse”—necessitating a return to orchestrating the full customer lifecycle as a cohesive journey.

2. The Emergence of the Go-to-Market Engineer

Timestamps: [11:23]–[22:32]

• Definition and Context:
  GTM Engineers blend sales process expertise, data, engineering, and now AI:
  “My GTM engineer is helping me build an agent... encode that using Vercel workflows in code that's both deterministic and less so.” ([13:33])
• From Manual to AI-Driven Outbound:
  Jeanne’s early Stripe story: building a “company universe” database to Mad Libs outbound emails, which failed without AI, but “now... works” with AI/agents at Vercel ([14:21])
• Impact:
  Automating lead qualification—inbound SDR’s work—allowed Vercel to reduce from 10 SDRs to 1 with AI agent and keep conversion rates flat while reducing time & touches ([20:37])
• SDR/AE Explained:
  Simple breakdown: “SDR is pipeline generation... Account executives are closers.” ([24:01])
• Reallocation of Human Talent:
  With AI handling rote tasks, salespeople spend “70% of their time interacting with humans,” moving up the value chain ([18:18], [20:31])
• On Whether AI Will Replace SDRs:
  “No one graduated from college to become an SDR... what we’re doing is shifting folks into something that uses more of their full capacity” ([22:32])

3. Tools and Internal AI Agents

Timestamps: [34:33]–[43:10]

• Agent-Driven Sales Intelligence:
  Vercel uses agents to analyze Gong transcripts, Slack, and emails for deal/loss insights (“Lost Bot,” “Deal Bot”), surfacing issues like missing economic buyers or objection handling ([34:33])
• Cultural & Cost Impact:
  “That deal bot... was like two days. He had it 40 hours later.”
  “Lead agent which runs full stack on Vercel will cost us about $1,000 to run for the entire year. I got that [SDR] down from ten people to one... 90+% reduction in total cost.” ([42:31])
• Build vs. Buy:
  “It’s not that hard to build these agents and they aren’t that expensive... the alpha is essentially in building your own stuff” ([43:10])
• Platform Recommendations:
  Most GTM engineers were sales engineers with coding ability: “We’re just building from the ground up here... Vercel platform is making it that easy to use our framework...” ([44:51])

4. Treating Go-to-Market as a Product

Timestamps: [46:37]–[52:30]

• Mindset Shift:
  “The experience that you have of being sold to will increasingly actually differentiate a company and drive buying decisions if products are only different at the margin.” ([46:56])
• Designing Experiences:
  Stripe’s whiteboarding as first call; customer walks away with architecture diagram and insight.
  “You need to go through from the first time you become aware the company exists to that five-year, heavily retained... customer, a set of experiences.” ([46:56])
• Add Value at Every Touchpoint:
  “Adding value at any touch point, regardless of whether or not that customer bought... Those you lose, return years later.” ([50:43])

5. Tactical Go-to-Market Advice

Timestamps: [52:38]–[57:55]

• Unique Insights Win:
  Use data to benchmark prospects vs. peers and reveal “suboptimal” choices.
• “Listen More, Talk Less” ([55:43]):
  “Excellent salespeople typically talk well under half the time in a conversation.”
• Shift from Pain to Competitive Advantage:
  “Rather than focusing on the pain... focus on how you will be better than your competitors... show the alpha you can achieve if you use [your product].” ([57:55])
• Risk Aversion Drives Buying:
  “80% of customers buy to avoid pain or reduce risk as opposed to increase upside.” ([58:27])

6. Segmentation Masterclass

Timestamps: [60:44]–[69:31]

• Frameworks:
  Move beyond “SMB / Mid-market / Enterprise”—add axes like growth potential, business model, traffic (for Vercel), and workload type.
• How to Start:
  “I sat down with our head of data science, said ‘what drives revenue? What attributes tell you this is a $100K vs. $1M customer?’” ([65:31])
• Keep It Simple:
  “Three attributes is something you can reason about.” ([68:19])
• Segmentation Is Org-Wide, Not Just Sales:
  “A lot of times folks think segmentation is a go to market thing. I really think it's a company thing.” ([68:19])

7. Building Sales Orgs That Engineers Love

Timestamps: [69:31]–[74:00]

• Sales Org Disguised as Product:
  “If you are an account executive in my org... it should take [engineers] ten minutes to figure out you aren’t a product manager.” ([69:59])
• Sales as R&D:
  “The best go to market orgs are equal parts revenue-driving and R&D... translating all that feedback into the roadmap.” ([69:59])
• Partnering, Not Just Requesting:
  “Company strategy is product strategy meets go to market strategy... constantly trying to figure out, how do I make more money more efficiently?” ([73:00])

8. Product-Led Growth (PLG) & Pricing

Timestamps: [74:00]–[79:24]

• PLG Still Relevant, But...
  “It does typically have a ceiling... People are generally not going to give a million dollars via a self-serve flow.”
  “Where companies hit walls is when they don’t add the sales portion of it soon enough.” ([74:27])
• Strategic Pricing:
  “Think about pricing like a product... sometimes you’re grossly undercharging... or defaulting to freemium without a strategy.” ([76:52])

9. Sales Comp & Hiring**

Timestamps: [79:41]–[82:22]

• Hot Take:
  “Sales comp... makes your organization less flexible because you basically have to decide 12 months in advance... what you value.” ([79:41])
• Hiring Philosophy:
  Blend traditional sales talent with consulting/banking backgrounds for analytical depth and consultative skills ([79:41])

Notable Quotes & Memorable Moments

• On Customer Buying Motives:
  "80% of customers buy to avoid pain or reduce risk as opposed to increase upside."
  — Jeanne, [58:27]

• On Go-to-Market Experience:
  "The experience that you have of being sold to will increasingly actually differentiate a company and drive buying decisions if products are only different at the margin."
  — Jeanne, [46:56]

• On AI & SDR Efficiency:
  “We had 10 SDRs doing this inbound workflow and now we just have one that is effectively QAing the agent. The other nine we deployed on outbound.”
  — Jeanne, [20:31]

• On AI Lead Agent Cost:
  “That lead agent... will cost us about $1,000 to run for the entire year. I got that down from ten [SDRs] to one.”
  — Jeanne, [42:31]

• On Building Human-Like Sales Orgs:
  "If you are an account executive in my org, and I put you in front of 10 engineers at our company, it should take them 10 minutes to figure out you aren't a product manager."
  — Jeanne, [69:59]

• On the Role of AI in Internal Productivity:
  “You may find that it’s meaningfully easier than you think, and you get returns pretty quickly.”
  — Jeanne, [43:10]

• On Personal Philosophy (Lightning Round):
  “When the going gets tough, the tough get going... there's always a way.”
  — Jeanne, [82:54]

Recommended Episode Timestamps

| Segment & Topic | Timestamp | |-------------------------------------------|------------------| | Go-to-Market Defined | [05:50]–[08:44] | | GTM Engineer & AI in Sales | [11:23]–[22:32] | | Tools & Agents — Internal AI Use Cases | [34:33]–[43:10] | | Go-to-Market as a Product | [46:37]–[52:30] | | Tactical Sales Advice | [52:38]–[57:55] | | Segmentation Frameworks | [60:44]–[69:31] | | Building Engineering-Friendly Sales Orgs | [69:31]–[74:00] | | PLG Realities & Pricing Strategy | [74:00]–[79:24] | | Sales Comp & Hiring Philosophy | [79:41]–[82:22] | | Lightning Round — Life Philosophy | [82:45] onward |

Final Reflections

Jeanne DeWitt Grosser’s frameworks and stories offer a blueprint for building not just a modern sales team, but an integrated, AI-empowered GTM engine that partners with product, leverages data and AI, and delivers highly differentiated customer experiences. Listeners will leave with both actionable tactics and inspiration to reimagine how they think about go-to-market—from first outbound email to a decade-long customer journey.

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