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

Overview

This episode dives into the evolving landscape of go-to-market (GTM) strategies, particularly in the AI era. Jeanne DeWitt Grosser, COO of Vercel, shares insights on the rise of the go-to-market engineer, the importance of segmentation, and how to build sales organizations that align seamlessly with product and engineering teams. She also discusses the changing dynamics of pricing, sales compensation, and the balance between product-led growth (PLG) and sales-driven strategies.

Notable Quotes

- 80% of customers buy to avoid pain or reduce risk as opposed to increase upside. – Jeanne DeWitt Grosser, on understanding customer motivations.

- The litmus test I have always given my sales team is 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 DeWitt Grosser, on building a sales team that earns engineers' respect.

- Yeses are great, nos are great, maybes will kill you. – Jeanne DeWitt Grosser, on the importance of clarity in sales outcomes.

🚀 The Rise of the Go-to-Market Engineer

- GTM engineers are transforming sales by automating workflows and leveraging AI to optimize processes.

- At Vercel, GTM engineers shadow top-performing sales reps to replicate their workflows with AI agents, enabling one SDR to do the work of ten.

- AI tools like lead agents and deal bots are used to automate tasks such as lead qualification, outbound prospecting, and real-time sales insights.

- These innovations reduce costs significantly (e.g., replacing a $1M SDR team with a $1,000 AI agent) and improve efficiency.

📊 Mastering Segmentation

- Effective segmentation is critical for targeting the right customers and optimizing sales strategies.

- Companies should consider multiple dimensions, such as size, growth potential, and specific business models or workloads.

- For example, Stripe segmented customers by size (SMB, mid-market, enterprise), growth potential, and business model (B2B, B2C, marketplace).

- Vercel uses traffic data and workload type to prioritize high-value customers like OpenAI, which, despite being a mid-sized company, is treated as enterprise due to its high web traffic.

🤝 Building Sales Teams That Collaborate with Product and Engineering

- Sales teams should have deep product knowledge to gain credibility with engineers and provide valuable feedback to product teams.

- Jeanne emphasizes that sales teams should act as an extension of the product management team, discerning market signals and feeding insights into the roadmap.

- A diversified sales team, combining traditional sales experience with analytical backgrounds (e.g., consulting or banking), fosters a collaborative and innovative environment.

💡 Go-to-Market as a Product

- Jeanne advocates for treating the GTM process like a product, focusing on creating a seamless and valuable customer journey.

- Examples include offering whiteboarding sessions instead of traditional discovery calls and providing unique insights (e.g., benchmarking website performance) to add value at every touchpoint.

- The goal is to make the sales process feel like a personalized, human experience rather than a transactional interaction.

💸 Rethinking Pricing and Sales Compensation

- Pricing should align with customer value and company costs, and it should be treated as a product that evolves over time.

- Vercel recently unbundled its enterprise SKU to make features more accessible to startups, boosting its PLG funnel.

- Jeanne critiques rigid sales compensation plans, advocating for more flexibility to adapt to rapidly changing market conditions, such as the introduction of new products mid-year.