Chief Product Officer (CPO) Location: Toronto, Ontario (Hybrid) or Montréal, Québec (Hybrid) Reports to: CEO Direct Reports: Product Management, Product Design Level: Executive / C-Suite About Us Trolley is the payouts platform for the internet economy. Our mission is to unlock the global economic opportunity of the internet by building a truly borderless payouts ecosystem. Through our platform and API, Trolley enables businesses to pay people anywhere in the world, supporting creators, on-demand workers, and suppliers at scale.

Companies rely on Trolley as mission-critical infrastructure to automate payouts, collect tax and banking information, and reduce fraud and risk, all in one place. Today, Trolley is the trusted payouts solution for hundreds of businesses, including Canva, SoundCloud, and Envato. We've processed millions of payments globally, helping creators, artists, and suppliers get paid quickly, securely, and with confidence.

As Trolley enters its next stage of growth, we are investing heavily in AI to accelerate product innovation, create exceptional customer experiences, and strengthen our leadership position in global payments infrastructure. We are seeking a Chief Product Officer (CPO) to define our product vision, shape our long-term strategy, and lead the evolution of our platform. The Opportunity The Chief Product Officer will be a key member of Trolley's Executive Leadership Team, responsible for defining and executing the company's product vision, strategy, and roadmap.

The successful candidate will bring deep experience building and scaling enterprise B2B SaaS products within fintech, payments, financial infrastructure, embedded finance, or banking technology.

Requirements

, security, and reliability are fundamental to success. Working closely with the CTO, the CPO will ensure Trolley continues to build products that solve meaningful customer problems, strengthen our competitive position, and accelerate sustainable growth. While the CTO is accountable for technology strategy, engineering execution, platform architecture, AI enablement, and Information Security, the CPO owns product vision, customer value, product strategy, and commercial success across the platform.

The CPO will lead Product Management and Product Design while partnering closely with Engineering, Customer Success, Sales, Marketing, Compliance, Finance, Operations, and Risk. A key priority for the successful candidate will be defining how AI creates differentiated customer value through intelligent automation, workflow optimization, and innovative product capabilities that help customers move money globally with greater speed, confidence, and efficiency.

, and technical investment to maximize long-term value. Partner with the CEO and Executive Leadership Team to shape company strategy. Lead Product Innovation Define product strategy across global payouts, tax, compliance, APIs, financial workflows, and future platform capabilities.

Build products that simplify complex global payment operations while maintaining the highest standards of security, compliance, and reliability. Drive product discovery through customer research, market analysis, competitive intelligence, and data. Champion continuous experimentation, customer validation, and iterative product development.

Ensure Trolley remains at the forefront of innovation within the global payments ecosystem.

What You'Ll Do

Define and Execute Product Strategy Define and execute Trolley's long term product vision and strategy. Own and prioritize the company wide product roadmap. Align product investments with company strategy, customer needs, and commercial priorities.

Identify opportunities to expand Trolley's platform, strengthen competitive differentiation, and enter adjacent markets.