Head of AMER Startups (AI Sales)

The shape of it

In the posting’s own words

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 it asks for · 5

• 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.

Also a plus

• 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.

What the job covers

• 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).

Tools and skills named

Words the posting leans on

• startups11×
• models9×
• sales8×
• specialized7×
• coverage6×
• product6×
• billing5×
• ecosystem5×
• infrastructure5×
• monetization5×
• experience4×
• founder4×
• leadership4×
• leading4×
• managers4×
• market4×

Counted from the posting after the mission statement and the legal notices are set aside. The ones near the top are the ones a screener is looking for.

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