Jeanne DeWitt Grosser, the current Chief Operating Officer of Vercel and former Chief Business Officer at Stripe, is a prominent figure in the tech industry known for her expertise in scaling sales organizations, driving go-to-market strategies, and leading with a product-centric mindset. Through various interviews and talks, she has shared a wealth of knowledge for professionals in sales, leadership, and business strategy.
On Sales Philosophy and Strategy
A recurring theme in Grosser's advice is the fundamental role of sales in solving customer problems and the importance of a deep understanding of the product. She emphasizes that the best sales teams act as a vital link between the customer and the company's research and development.
Key Quotes and Learnings:
- Sales as Problem-Solving: "Sales is fundamentally about solving problems. People ultimately buy from you when they feel you're going to help them solve a legitimate problem that they have."[1]
- Sales as R&D: "The best salespeople and sales organizations are 50% revenue-generating and 50% R&D because they're out there talking to customers every day."[1]
- The Power of Product Knowledge: Grosser stresses the value of deeply knowing your products and customers, a lesson she learned early in her career. This expertise can lead to influential roles in discussions beyond one's immediate job description.
- Hope is Not a Strategy: Especially in sales, she advises being upfront to get a clear "yes" or "no" to move forward effectively.[2]
- Understanding the 'Why': Before building a sales playbook, it is crucial to understand the foundational elements of what makes the product and company successful.
- The Concentric Circle Idea: When expanding into the enterprise market, focus on companies that are "one concentric circle from where we had product market fit today," rather than pursuing entirely new and unrelated product areas.[2]
- Don't Sell When the Internet Can: For smaller companies and simple use cases, a salesperson isn't always necessary. A strong self-service engine can be more effective.[1]
On Leadership and Building Teams
Grosser’s leadership philosophy is rooted in the "platinum rule"—managing people as they need to be managed. She champions building diverse teams and fostering a culture that aligns with the broader company values.
Key Quotes and Learnings:
- The Platinum Rule of Management: "Manage others the way they need to be managed, not the way that you personally like to be managed."
- Hiring for Diversity of Background: "I'm a big fan of diversity of background... Each type of person is going to up everyone else's game."[3]
- Avoiding Common Pitfalls for New Sales Leaders: She warns new leaders against staying in an individual contributor mindset, failing to align with the product organization, and chasing any opportunity without a clear strategy.[3]
- Founders and the First Sales Hire: Grosser suggests that founders should initially lead the sales efforts to create a playbook before hiring a dedicated salesperson.
- Aligning Sales Culture with Company Culture: A sales leader should develop a team culture that resonates with the overall company culture to ensure cohesion and shared understanding.
On Go-to-Market Strategy and Product-Led Growth (PLG)
With extensive experience at product-led companies like Google, Stripe, and Vercel, Grosser offers nuanced perspectives on implementing and scaling PLG and enterprise sales motions.
Key Quotes and Learnings:
- Defining Product-Led Growth: She describes PLG as having two key components: a robust self-service engine for the lower end of the market and a bottoms-up sales approach where users adopt the product before a top-down executive decision is made.[1]
- Knowing When to Layer in Sales: A critical aspect of PLG is understanding the right moment to introduce a human sales touch for larger or more complex customers.[1]
- Go-to-Market as Experimentation: "Go-to-market strategy is very complicated, and in many cases, there are no obvious answers. If you want to do it well, there's a lot of experimentation."[1]
- Building an Operating Model from the Ground Up: Instead of just having a top-down revenue goal, she advocates for a granular, bottom-up model that outlines what needs to be true to hit that target, often referring to this as "funnel math."[4]
- Signals for Moving Upmarket: Two strong indicators that it's time to move upmarket are when your existing customer base is pulling you in that direction and when you start achieving meaningful, not just experimental, wins in the enterprise segment.[4]
- Pricing Evolution for Enterprise: Simple, consumption-based pricing that works well for SMBs often needs to be unbundled and made more modular to meet the enterprise need for predictability and the ability to buy solutions.[4]
On Building an AI-Native Business
At Vercel, Grosser is at the forefront of building an AI-native company. Her insights focus on the speed of innovation and the strategic advantages of integrating AI into the core business operations.
Key Quotes and Learnings:
- AI as a Foundational Design Choice: At Vercel, AI is not an add-on but a core part of the company's operational architecture.
- The Golden Age of Storytelling: In a world with a low barrier to entry for content creation, she believes courage in storytelling and having a distinct point of view is more important than ever to cut through the noise.
- Decision Velocity in AI-Native Companies: AI-native companies are able to ship new features and products at an incredibly fast pace, sometimes multiple times a day.
On Career and Personal Growth
Grosser's reflections on her own career path offer valuable lessons on continuous learning and the importance of building external networks.
Key Quotes and Learnings:
- Be Hypothesis-Driven: To continuously improve, she advises having a point of view on what is likely to happen. This allows for more effective learning and iteration when the actual outcome is observed.[2]
- The Value of an External Community: She encourages professionals to actively build their external network sooner in their careers to gain diverse perspectives and share knowledge.
- Don't Let Your Job Description Define Your Role: Proactively seeking to understand and solve problems across the business can lead to greater influence and impact.[5]
- Apply First Principles: While it's important to know best practices, one shouldn't blindly follow what worked in a different context. It's crucial to apply first principles to the specific situation.
While this list provides a comprehensive overview of Jeanne DeWitt Grosser's publicly shared wisdom, it is not exhaustive. Her insights continue to shape the strategies of high-growth technology companies and offer a valuable guide for leaders and aspiring professionals in the ever-evolving tech landscape.
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