Headquarters: Toronto, Remote- Canada

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 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 Growth team owns the Stripe product-led growth motion for self-serve customers, primarily startups and SMBs. We're responsible for acquiring, onboarding, and growing every business in the world on one or more Stripe products. The team works across the full user lifecycle (signup, onboarding, activation, expansion, and retention) and sits at the intersection of product, data science, engineering, design, marketing, and AI and ML. We're directly accountable for topline self-serve revenue.

What you'll do

The largest Stripe customers get a dedicated product specialist who understands their business, recommends the right products, and guides them through onboarding and expansion. This role exists to bring that same quality of guidance to every Stripe user, leveraging AI, at scale.

You'll define and build the experience that delivers personalized guidance leveraging AI across the full user journey, from first question through activation and expansion. Inbound users range from early-stage startups picking their first product to larger prospects who need a sales engagement. Your system must match each user to the right path and ensure no one falls through the cracks. Stripe has strong building blocks in this area (product recommendations, onboarding flows, merchant context, and outreach infrastructure), but no unified motion tying them together. Your role is to define the AI specialist motion, ship it, and own the revenue it generates.

You'll start with inbound prospects, then extend into onboarding, cross-sell, and outbound, building a system where each interaction makes Stripe smarter about what a business needs and when.

Responsibilities

• Define the AI specialist—what it knows, how it engages, where it draws the line, and when it hands off. Own the product vision, strategy, and roadmap.
• Launch and scale the inbound motion across chat, voice, and email for prospects and new users seeking help with products, pricing, and getting started. Drive rapid iteration on answer quality and resolution rates.
• Build the triage and qualification layer. The AI specialist must assess the user it is engaging with, understand the size and complexity of the opportunity, and route accordingly, guiding smaller users through their full journey while qualifying larger prospects and handing them to sales with rich context.
• Define escalation paths to the vendor support team and sales team. Ensure that handoffs are seamless, context is preserved, and no user interaction is left unresolved.
• Scale past the first interaction into onboarding and cross-sell, leveraging existing Stripe product recommendation, merchant context, onboarding systems, and outreach platform to help users activate products, discover new ones, and grow their usage of Stripe.
• Own the revenue this motion produces. Define success metrics and maintain accountability from conversion through expansion, including pipeline generated through AI-qualified leads.
• Partner with engineering, AI and ML, design, data science, marketing, sales, and support to execute at pace while maintaining the Stripe bar for quality and trust.

Who you are

We're looking for someone who meets the minimum requirements to be considered for the role. If you meet these requirements, you are encouraged to apply. The preferred qualifications are a bonus, not a requirement.

Minimum requirements

• 5+ years of product management experience, taking products from strategy through to shipped outcomes
• Experience building AI-powered, conversational, or agentic products. You understand what it takes to ship AI that works reliably for real users, not just in demos.
• A track record of owning revenue or business outcomes through product-led approaches
• Experience with hypothesis-driven product development and experimentation at scale
• Ability to work across existing systems and synthesize them into a coherent product strategy rather than defaulting to net-new builds
• Strong written and verbal communication, with the ability to drive alignment across a broad set of stakeholders
• An ownership mindset. You do what it takes to solve problems and ship.

Preferred qualifications

• Experience with growth problems (acquisition, activation, and onboarding) in B2B or B2B2C environments
• Hands-on familiarity with LLMs, conversational AI, or agentic architectures. You have shipped products on top of these technologies, not just evaluated them.
• Experience building across channels (chat, email, and voice) with an understanding of the tradeoffs between modalities
• Background in scaling high-touch human experiences (sales, support, and product specialists) through technology
• Comfortable in high-visibility roles with direct accountability for business outcomes

To apply: