Head of Startup Sales (Grower) - AMER

Who we are About Stripe Stripe is a financial infrastructure platform for businesses. Millions of companies - from the world’s largest enterprises to the most ambitious startups - use Stripe to accept payments, grow their revenue, and accelerate new business opportunities. Our mission is to increase the GDP of the internet, and we have a staggering amount of work ahead. That means you have an unprecedented opportunity to put the global economy within everyone's reach while doing the most important work of your career. About the team The AMER Startups Sales team is responsible for Stripe's fastest-growing customer segment, the companies that will become the platforms, networks, and enterprises of the future. You will be tackling the "founder's dilemma" at scale: how do we maintain the intimacy of a 1:1 relationship with thousands of companies, while building highly intelligent systems that scale? Startups represent a disproportionate share of Stripe's long-term value, and this team ensures those relationships deepen over time. What you’ll do As Head of Startup Sales (Grower), you will lead the organization responsible for growing and expanding Stripe's relationships with thousands of startup accounts post-activation. This is an expansion engine for the highly strategic Startups segment. Your teams will drive multi-product adoption, identify and act on growth signals, and build coverage models calibrated for the unique economics of high-growth startups. You will be a second-line leader managing frontline managers across multiple specialized sub-teams, each with distinct operating rhythms and coverage ratios. You'll partner cross-functionally with product specialists, solutions architects, customer success, and marketing to build the motions that turn early-stage activations into deep, multi-product platform relationships. This role reports to the Head of Startups. • Develop the long-term vision and operating model for Startup (Grower), building specialized sub-teams with distinct charters • Drive multi-product expansion across a large portfolio of accounts at varying stages of growth, from pre-PMF through rapid scale • Build and operationalize structured expansion cadences, ensuring every high-potential account has a product-attach strategy • Design coverage models that balance high-touch investment on the highest-growth accounts with signal-driven, AI-augmented coverage at scale • Partner with product specialist teams (billing, treasury, platform products) to build co-sell motions that compound revenue across the Stripe platform • Create the systems that detect breakout accounts accelerating within the portfolio, and ensure they receive the right coverage at the right moment • Make hiring decisions, refine ideal candidate profiles by sub-team, and build a team development engine that grows AEs from early-career through senior • Design comp and incentive structures that reward expansion and product depth • Own the forecasting and pipeline operating rhythm for a segment with unique leading and lagging indicators • Work cross-functionally across Product, Engineering, Marketing, and Operations to shape Stripe's startup experience and influence roadmap priorities based on what you hear from customers Who you are We are looking for a candidate with proven success scaling tech sales teams, strong analytical and relationship-building skills, and a genuine passion for the startup ecosystem. Minimum requirements • 10+ years of experience leading high-growth sales organizations, with 3+ years as a second-line manager, specifically building specialized sub-teams with distinct operating models. • Proven success driving multi-product platform growth through value-based selling, structured expansion funnels, cross-sell motions, and customer lifecycle design. • Strong systems thinker with quantitative skills to model portfolio economics, coverage ratios, and signal-driven investment decisions. • Ability to hire and develop high-performance AEs across various seniority levels while managing long-horizon economics and compounding returns. • Demonstrated success partnering cross-functionally with product, specialist overlays, and customer success teams in a complex platform environment. Preferred Qualifications • Experience with startups as customers, understanding the nature of high-growth companies and require purpose-built coverage • Prior experience at a high-growth technology or infrastructure company • Familiarity with payments, fintech, or financial infrastructure • Experience designing comp plans for expansion-focused teams • Track record of building or leveraging AI/automation to scale coverage beyond linear headcount growth Leadership Style You are a "player-coach" who can zoom into the details of a specific startup’s strategy while simultaneously zooming out to shape our long-term operating rhythm. You ensure the customer remains the north star of everything that we do and that our growth motions genuinely deliver value at every stage of the startup lifecycle.You thrive in high-velocity environments and can lead through influence in a matrixed organization. You will embody Stripe’s core operating principles in your day-to-day leadership: • User first: You will advocate for the startup founder’s experience, ensuring our growth motions and product expansions solve genuine business problems for our users. • Stay curious: You will constantly seek to understand the evolving startup landscape, experimenting to improve how we serve our fastest-growing segment. • Collaborate egolessly: You will work seamlessly across Stripe prioritizing the collective success of the Startups mission over individual or team-specific accolades.