This case study follows Jeanne DeWitt Grosser’s tenure at Stripe as she architected the company’s sales organization from the ground up during a period of exponential growth. As Stripe evolved from a developer-focused startup to a multibillion-dollar fintech powerhouse, DeWitt Grosser spearheaded the effort of building a sales function that would accelerate growth while preserving the company’s engineering-led culture. The case introduces the consumption-based billing business model and the unique challenges it poses for sales planning compared to other traditional SaaS models. Through the Stripe story, the case explores how the consumption-based billing model shaped critical decisions around the sales organization model, including the ideal AE profile, Hunt-and-Hold versus Hunt-and-Grow organization structure, compensation plans, and staffing decisions. Readers will get insights into Stripe’s strategic pivot to outbound sales, its thinking around ideal customer profiles (ICPs) as the company scaled upmarket, and the development of its first sales playbook. The case also examines DeWitt Grosser’s approach to sales capacity planning—balancing ambitious top-down growth ambitions and bottoms-up data—ultimately presenting her dilemma as she contemplates the next phase of Stripe’s sales organization to fuel continued growth.
