Head of AMER Startups (AI Sales)

Stripe; San Francisco (CA); On-site; USD 390,000 - 584,000; Full time

Benefits offered by this job

Equity

Sales bonuses

401(k) plan

Medical insurance

Wellness stipend

Job summary

Stripe is seeking a strategic Head of AMER Startups (AI Sales) to lead the dedicated AI startups team across North America. You will scale coverage, drive multi-product adoption, and shape monetization models around usage and tokens while partnering with product, risk, and ecosystem partners.

You will manage frontline managers and Account Executives, build go-to-market motions, and forecast pipeline for a volatile, high-growth segment.

Qualifications

• 10+ years leading high-growth tech sales or GTM organizations.
• 3+ years as a second-line manager leading multiple specialized sales sub-teams.
• Experience with usage-based, consumption, or complex SaaS billing models.
• Proven track record of driving multi-product platform adoption and cross-sell growth.
• Strong quantitative, analytical, and systems thinking skills to model portfolio economics.

Responsibilities

• Define GTM vision, sub-team structure, and operating model for Stripe’s AI Startup org in North America.
• Design coverage models optimized for high-growth trajectories with hybrid sales coverage.
• Drive adoption of Stripe core products (Metered/Usage-Based Billing, Connect, Financial Connections, Global Payouts) for AI pricing.
• Create data-driven breakout detection signals to identify fast-growing AI companies and allocate resources accordingly.
• Partner with AI venture funds, incubators, and cloud providers to position Stripe as the default financial stack for AI startups.
• Recruit, hire, and develop frontline leaders and Account Executives in the AI sales team.
• Shape roadmap priorities for billing engine scalability, usage metering, and AI payments capabilities.
• Own pipeline health and revenue forecasting for a volatile, high-growth segment.

Skills

Leadership experience

GTM strategy

Usage-based billing

Multi-product adoption

Data-driven decisions

Job description

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.

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).

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, new business models, and founder needs to keep Stripe ahead of market shifts.
• Collaborate Egolessly: You work seamlessly across Stripe, prioritizing the overarching success of the Startups mission and the broader AI ecosystem over individual or team-specific metrics.

In-office expectations

Office-assigned Stripes in most of our locations are currently expected to spend at least 50% of the time in a given month in their local office or with users. This expectation may vary depending on role, team and location. For example, Stripes in Stripe Delivery Center roles in Mexico City, Mexico, Bengaluru, India, and Dublin, Ireland work 100% from the office. Also, some teams have greater in-office attendance requirements, to appropriately support our users and workflows, which the hiring manager will discuss. This approach helps strike a balance between bringing people together for in-person collaboration and learning from each other, while supporting flexibility when possible.

Pay and benefits

The annual US base salary range for this role is $389,600 - $584,400. For sales roles, the range provided is the role’s On Target Earnings ("OTE") range, meaning that the range includes both the sales commissions/sales bonuses target and annual base salary for the role. This salary range may be inclusive of several career levels at Stripe and will be narrowed during the interview process based on a number of factors, including the candidate’s experience, qualifications, and location. Applicants interested in this role and who are not located in the US may request the annual salary range for their location during the interview process.

Additional benefits for this role may include: equity, company bonus or sales commissions/bonuses; 401(k) plan; medical, dental, and vision benefits; and wellness stipends.

We look forward to hearing from you.

At Stripe, we're looking for people with passion, grit, and integrity. You're encouraged to apply even if your experience doesn't precisely match the job description. Your skills and passion will stand out—and set you apart—especially if your career has taken some extraordinary twists and turns. At Stripe, we welcome diverse perspectives and people who think rigorously and aren't afraid to challenge assumptions. Join us.

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