What world-class GTM looks like in 2026 | Jeanne DeWitt Grosser (Vercel, Stripe, Google)

Nov 30, 2025 1h 26m 18 insights Episode Page ↗
Jean Grosser, COO at Vercel and former CBO at Stripe, discusses building world-class go-to-market teams. She shares insights on leveraging AI for sales, treating GTM as a product, effective segmentation, and fostering strong collaboration between sales, product, and engineering.
Actionable Insights

1. Build Sales Org with Product Depth

Cultivate a sales organization where account executives possess incredible product depth, making them indistinguishable from product managers to engineers. This fosters credibility with product and engineering teams and enables sales to act as an R&D extension by translating customer feedback into valuable roadmap signal.

2. Treat Go-To-Market as a Product

Design the customer buying journey like a product, focusing on creating unique, human, and personalized experiences rather than transactional interactions. This differentiation becomes crucial when technical product differences narrow, driving buying decisions based on how customers feel about being sold to.

3. Leverage AI for Sales Automation

Utilize AI agents to automate rote sales tasks like research, follow-ups, and initial prospecting, aiming for salespeople to spend 70% of their time interacting with humans. This increases efficiency and allows sales teams to focus on deeper customer engagement.

4. Keep Human in AI Sales Loop

Implement AI agents for sales workflows with a ‘human in the loop’ approach, especially for critical tasks like lead qualification and crafting responses. Have humans review and send AI-generated outreach to ensure brand consistency and quality, while using agent feedback for continuous improvement.

5. Diagnose GTM Process with AI

Use AI agents to analyze Gong transcripts and other interactions to diagnose ‘bugs’ in your go-to-market process, such as poor objection handling or common sticking points. Run regular sprints to address these identified issues with new content, discovery guides, or demo changes.

6. Focus on Risk Reduction for Buyers

Understand that 80% of customers buy to avoid pain or reduce risk, rather than to increase upside. Frame your sales narrative around de-risking potential negative outcomes for enterprises and helping customers avoid not making revenue targets or being outdone by competitors.

7. Implement Collaborative Discovery Sessions

Replace traditional discovery calls with collaborative whiteboarding sessions where customers draw their architecture. This approach helps you learn about their stack and challenges, while providing customers with a valuable asset and a sense of partnership.

8. Add Value at Every Touchpoint

Strive to add value to customers at every touchpoint, even if they don’t buy immediately. Providing unique insights or helpful information builds trust and ensures that customers may return for future buying cycles.

9. Invest in Data for Unique Insights

Invest in data to uncover unique insights about a prospect’s current performance or suboptimal state. Share these data-driven insights immediately to pique interest, demonstrate value, and establish your company as a trusted, knowledgeable resource.

10. Create Well-Architected Guides

Beyond basic documentation, develop ‘well-architected guides’ or blueprints that outline best practices for implementing your product within specific customer setups. This is especially valuable for larger companies seeking detailed implementation guidance.

11. Practice Excellent Discovery Skills

Master the art of discovery by talking less than half the time in conversations, asking probing questions, and employing techniques like ‘five whys’ to go deep. Help customers arrive at conclusions on their own rather than immediately problem-solving.

12. Develop a Company-Wide Segmentation

Establish a clear segmentation framework that is understood across the entire company, not just go-to-market. This ensures product managers build with specific customer profiles in mind, aligning product and GTM strategies.

13. Use Data to Define Segmentation

Define your market segmentation by analyzing data to identify customer attributes that correlate with high revenue potential and repeated success. This helps you cluster winning customers and understand where your product resonates most effectively.

14. Build a General Manager Sales Org

Foster a sales organization that thinks like general managers, focused on building the business rather than just closing deals. This means understanding when to say no to feature requests and discerning market opportunities from mere objections.

15. Think About Pricing Like a Product

Approach pricing as a product, deeply understanding where customers derive value and where your company incurs costs. Align these factors smartly to avoid underpricing and ensure optimal revenue outcomes and customer experience.

16. Strategize Freemium Carefully

Do not default to a freemium strategy without a clear, intentional purpose. Evaluate if a free tier genuinely drives conversion or if the product’s integration effort means users are likely to stay regardless, potentially making a free trial unnecessary.

17. Diversify Sales Team Hiring

Build a diversified sales team by combining experienced salespeople with individuals from non-traditional backgrounds like consulting or banking. This mix fosters a richer learning environment where different skill sets (e.g., quantitative analysis, P&L understanding) are shared and developed.

18. Embrace ‘No’ as Data

Get comfortable with receiving ’no’ in sales, viewing it as valuable data rather than a setback. Use this information to understand why a deal was lost and inform future strategies or product improvements.