Head of AMER Startups (AI Sales)

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 start their business, 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 team is responsible for Stripe's fastest-growing and highest-potential customer segment. Within this organization, the AI Sales team focuses specifically on the breakthrough ecosystem of AI - spanning foundation model builders, AI infrastructure platforms, agentic workflows, and AI-native SaaS applications. AI startups represent an unprecedented paradigm shift: they achieve hyper-growth at velocities previously unseen in software, operate complex token- or consumption-based monetization models, and face unique infrastructure and scaling demands from day one. You will tackle the challenge of building dedicated coverage, specialized technical go-to-market motions, and intelligent automation systems to support thousands of AI companies as they scale from seed stage to market dominance. What you’ll do As Head of AMER Startups (AI Sales), you will lead the dedicated organization responsible for acquiring, expanding, and partnering with high-growth AI startups across North America. This role acts as both an expansion engine and a strategic acquisition vector for the most transformational segment in tech. You will be a second-line leader managing frontline managers across specialized Account Executives who grow distinct AI stages (e.g., early-stage AI labs, scaling AI infra, and enterprise-grade AI native apps). You will partner cross-functionally with product managers, solutions architects, risk specialists, and AI ecosystem venture partners to build GTM motions around usage billing, multi-product platform adoption, and AI-native monetization patterns. This role reports to the Head of AMER Startups. Responsibilities • Vision & Strategy: Develop the overarching GTM vision, sub-team structure, and operating model for Stripe’s AI Startup organization across North America. • Specialized AI Coverage: Design coverage models optimized for non-linear, hyper-growth trajectories—balancing high-touch high-velocity sales engineering for breakout AI labs with signal-driven, automated coverage for emerging AI developers. • Monetization & Product Attach: Drive adoption of core Stripe financial infrastructure—including Metered/Usage-Based Billing, Connect, Financial Connections, and Global Payouts—tailored specifically to consumption and token-based pricing models. • Breakout Detection Systems: Create data-driven systems and signals to identify early breakout AI companies (e.g., sudden compute expansion, API usage spikes) and rapidly deploy specialized resources to capture and retain market share. • Ecosystem Leadership: Partner closely with leading AI venture funds, incubators, AI compute providers, and cloud marketplaces to position Stripe as the default financial stack for AI startups. • Team Building & Management: Recruit, hire, and develop top-tier frontline managers and Account Executives, defining specialized AI sales profiles and fostering an environment of deep domain expertise. • Product Feedback Loop: Serve as the strategic voice of AI founders to Stripe’s Product and Engineering teams, shaping roadmap priorities for billing engine scalability, usage metering, and AI agent payment capabilities. • Forecasting & Operations: Own pipeline health and revenue forecasting for a volatile, hyper-growth segment using specialized leading metrics (usage volumes, API calls, compute commit signals). Who you are Minimum requirements • 10+ years of experience leading high-growth technology sales or GTM organizations, with 3+ years as a second-line manager leading multiple specialized sales sub-teams. • Demonstrated experience with usage-based, consumption, or complex SaaS billing and monetization models. • Proven track record of driving multi-product platform adoption and cross-sell growth in fast-moving technology environments. • Strong quantitative, analytical, and systems thinking skills to model portfolio economics, coverage ratios, and signal-driven investment decisions. • Demonstrated ability to recruit, develop, and retain high-performing frontline leaders and Account Executives. Preferred qualifications • Deep domain knowledge of the AI landscape, including LLMs, generative media, AI agent frameworks, and AI cloud infrastructure. • Active connections within the startup and venture capital ecosystem (AI founders, investors, and startup communities). • Prior sales leadership experience at a high-growth developer-focused, infrastructure, or fintech platform. • Experience designing incentive and compensation structures aligned with consumption and usage-driven revenue models. • Track record of leveraging AI and automated signal workflows internally to scale sales productivity and coverage beyond linear headcount growth. Leadership Style You are a "player-coach" who can dive deep into the technical architecture of a generative AI startup's billing stack while stepping back to execute long-term strategic plans for the overall AMER market. You thrive in rapid, dynamic environments, embrace ambiguity, and lead through cross-functional influence across Product, Marketing, Risk, and Engineering. You will embody Stripe’s core operating principles in your day-to-day leadership: • • User First: You advocate relentlessly for the AI founder, ensuring our products solve the unique payment and monetization friction points of AI-native software. • Stay Curious: You continuously study emerging AI architecture patterns, n