Head of AMER Startups (AI Sales)

The role

You will lead the organization responsible for acquiring, expanding, and partnering with high-growth AI startups across North America. You will manage frontline managers and partner cross-functionally to build GTM motions around AI-native monetization patterns.

What you will do

• Develop the overarching GTM vision, sub-team structure, and operating model for Stripe’s AI Startup organization across North America.
• Design coverage models optimized for non-linear, hyper-growth trajectories.
• Drive adoption of core Stripe financial infrastructure tailored to consumption and token-based pricing models.
• Create data-driven systems to identify early breakout AI companies.
• Partner with leading AI venture funds, incubators, AI compute providers, and cloud marketplaces.
• Recruit, hire, and develop top-tier frontline managers and Account Executives.
• Serve as the strategic voice of AI founders to Stripe’s Product and Engineering teams.
• Own pipeline health and revenue forecasting for the segment.

Required qualifications

• 10+ years of experience leading high-growth technology sales or GTM organizations
• 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
• Demonstrated ability to recruit, develop, and retain high-performing frontline leaders and Account Executives

Nice to have

• 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)
• High-growth developer-focused, infrastructure, or fintech platform sales leadership experience
• Experience designing incentive and compensation structures aligned with consumption and usage-driven revenue models
• Track record of leveraging AI and automated signal workflows internally

About the company

Stripe is a financial infrastructure platform for businesses. Its mission is to increase the GDP of the internet.