Head of AMER Startups (AI Sales)

Stripe•San Francisco, CA

13d

About The Position

Stripe is hiring a Head of AMER Startups (AI Sales) to lead the organization responsible for acquiring, expanding, and partnering with high-growth AI startups across North America. The role leads a dedicated sales organization serving AI companies, including foundation model builders, AI infrastructure platforms, agentic workflows, and AI-native SaaS applications. It is both an expansion engine and a strategic acquisition vector for this segment. This second-line leadership role manages frontline managers and specialized Account Executives covering AI companies at different stages, from early-stage AI labs to scaling infrastructure providers and enterprise-grade AI-native applications. The leader partners with Product, Solutions Architecture, Risk, and AI ecosystem partners to develop go-to-market motions for usage billing, multi-product adoption, and AI-native monetization. The role reports to the Head of AMER Startups. The position requires a player-coach who can engage with technical billing architectures while setting long-term strategy for the AMER market. The leader is expected to work effectively in fast-moving, ambiguous environments and influence cross-functional teams across Product, Marketing, Risk, and Engineering. They will advocate for AI founders, stay informed about emerging AI architectures and business models, and collaborate across Stripe in support of the Startups mission and broader AI ecosystem.

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-based, 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, including the ability 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.
Ability to engage with the technical architecture of a generative AI startup’s billing stack.
Ability to operate in rapid, dynamic environments, embrace ambiguity, and influence cross-functional teams.

Nice To Haves

Deep knowledge of the AI landscape, including LLMs, generative media, AI agent frameworks, and AI cloud infrastructure.
Active connections in 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 to scale sales productivity and coverage beyond linear headcount growth.

Responsibilities

Develop the 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 trajectories, combining 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, for consumption- and token-based pricing models.
Create data-driven systems and signals to identify early breakout AI companies and rapidly 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 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 segment using leading metrics such as usage volumes, API calls, and compute commitment signals.
Advocate for AI founders and ensure Stripe products address payment and monetization challenges faced by AI-native software.
Continuously study emerging AI architecture patterns, business models, and founder needs.
Collaborate across Stripe, prioritizing the Startups mission and the broader AI ecosystem.