Head of AMER Startups (AI Sales)

Stripe•San Francisco, CA

13d

About The Position

Stripe is hiring a leader for its AMER Startups AI Sales organization, which serves high-growth AI startups across North America, including foundation model builders, AI infrastructure platforms, agentic workflows, and AI-native SaaS companies. The role leads the organization responsible for acquiring, expanding, and partnering with these companies, and serves as both an expansion engine and a strategic acquisition channel. It is a second-line leadership position managing frontline managers across specialized Account Executive teams covering different stages of AI company growth. The role reports to the Head of AMER Startups. The leader will develop Stripe’s North American AI startup go-to-market strategy and operating model; create coverage approaches for companies with rapid, nonlinear growth; and drive adoption of Stripe financial infrastructure suited to usage- and token-based business models. The role also builds data-driven systems to detect emerging breakout companies, develops relationships across the AI startup ecosystem, recruits and develops sales leaders and Account Executives, and represents AI founders’ needs to Stripe Product and Engineering teams. It owns pipeline health and revenue forecasting for this fast-changing segment. The position calls for a player-coach who can engage with technical billing architecture while setting long-term strategy. The leader is expected to work effectively amid ambiguity and cross-functional complexity, advocate for AI founders, stay informed about evolving AI technologies and business models, and collaborate across Stripe in support of the broader Startups mission.

Requirements

10+ years of experience leading high-growth technology sales or go-to-market 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 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.

Nice To Haves

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, including 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 using AI and automated signal workflows internally to scale sales productivity and coverage beyond linear headcount growth.

Responsibilities

Develop the overarching go-to-market vision, sub-team structure, and operating model for Stripe’s AI Startup organization across North America.
Design coverage models for nonlinear, hyper-growth AI companies, balancing high-touch sales engineering for breakout AI labs with signal-driven, automated coverage for emerging AI developers.
Drive adoption of Stripe financial infrastructure, including Metered/Usage-Based Billing, Connect, Financial Connections, and Global Payouts, tailored to consumption- and token-based pricing models.
Create data-driven systems and signals to identify early breakout AI companies and deploy specialized resources to capture and retain market share.
Partner with AI venture funds, incubators, AI compute providers, and cloud marketplaces to position Stripe as the default financial stack for AI startups.
Recruit, hire, and develop frontline managers and Account Executives; define specialized AI sales profiles and foster deep domain expertise.
Represent AI founders’ needs to Stripe Product and Engineering teams and help shape roadmap priorities for billing scalability, usage metering, and AI agent payment capabilities.
Own pipeline health and revenue forecasting for the AI startup segment using leading metrics such as usage volumes, API calls, and compute commit signals.
Lead specialized Account Executive teams through frontline managers across different stages of AI company growth.
Collaborate across Product, Marketing, Risk, and Engineering, advocating for AI founders and supporting the broader Startups mission.