Product Manager

Staff Product Manager

Toronto, Ontario, Canada .
full-time . September 22, 2026

At Chexy, we're building modern financial tools for Canadians starting with their largest expenses. We turned rent, mortgages, tuition, insurance and other big bills into opportunities to earn rewards, improve cash flow and get more from money they already have to spend.

We're the first platform in Canada that lets users pay nearly any bill using their credit card, while unlocking meaningful benefits like cashback, points and financial flexibility. With billions in payments moving through Chexy and a rapidly growing customer base, we're building a consumer fintech brand that can become part of how Canadians think about paying all of their bills. We're backed by world-class investors including Khosla Ventures, Crossbeam Venture Partners, Venrex, Antler, and Air Canada.

We're hiring a Staff Product Manager to own major product areas end to end. You'll work directly with the Head of Product and founders, find and shape the opportunities that move the business, and drive them from hypothesis to launch to scale. We're looking for a generalist: someone who operates at the intersection of strategy, data, and engineering, and is comfortable in ambiguity, because at this stage the problems rarely arrive well-defined.

• Strategic. You find opportunities others miss. You're a systems thinker: you can take a messy pile of use cases and distill them into one simple, elegant solution, then build the case for why it wins.
• Analytical. You're comfortable in the grey. You can take raw, messy data (qualitative or quantitative) and pull out the actual problem, the real insight, the requirement that matters. You write your own queries and change your mind when the numbers tell you to.
• AI-forward and adaptable. You use modern AI tools as a core part of how you work, stay current on how the practice of product management is changing, and adapt fast when better methods emerge.
• Technically strong. You're a real technical partner to engineering. You can talk architecture and tradeoffs, work hand-in-hand to turn a logical design into a real technical architecture, and you're hungry to learn what you don't know yet so you can make better calls.
• A strong executor. You get things done. You've owned a product (or a big chunk of one) and know how to lead complex, cross-functional projects without losing momentum. You have a bias to ship: the fastest way to know if something works is to put it in front of users, so you ship, learn, and iterate.
• Entrepreneurial. You've been a founder or early employee at a high-growth startup. Failed companies count; we care about the reps, not the outcome. You're scrappy and happy to wear different hats: building a business case one day, mapping a workflow the next, negotiating details with a vendor the day after.
• Product taste. Years of shipping products people actually love. You have a strong eye for design and know what good looks like in consumer products.

Across all of it: clear communication. You can take something complicated and make it simple, without losing what matters.

• Own strategy, roadmap, and outcomes for one or more core product areas
• Take 0-to-1 bets from problem discovery through launch, then scale what works
• Run structured experiments: define hypotheses, instrument metrics, make calls based on data
• Work daily with engineering and design in tight loops
• Navigate the realities of payments in Canada: banking partners, compliance, risk, and rewards economics
• Raise the bar on product craft across the team

• Staff-level scope with direct access to founders and customers
• A product people genuinely love
• Backed by Khosla Ventures and other world-class investors
• Competitive salary and equity, health benefits, and a team that moves fast