Chief Product Officer

Trolley; Toronto; Hybrid; CAD 210,000 - 320,000; Full time

Benefits offered by this job

Leadership bonus

ESOP Program

Extended healthcare benefits

4 weeks paid vacation

Remote work from anywhere (30 days)

Gym membership allowance

MacBook Pro provided

Job summary

The Chief Product Officer (CPO) at Trolley will define the product vision, shape the long-term strategy, and lead the evolution of our payments platform. You will own the product roadmap, align with executive leadership, and drive cross-functional execution across Product, Design, Engineering, and Success.

You will lead a world-class team to deliver enterprise-grade B2B SaaS capabilities, with a focus on AI-enabled features, security, compliance, and reliability, enabling seamless global payouts

Qualifications

• 10+ years of progressive product leadership experience.
• Experience as a Chief Product Officer, VP Product, SVP Product, VP Product Management or equivalent executive within fintech/payments/financial infrastructure.

Responsibilities

• Define long term product vision and strategy for the platform.
• Lead Product Management and Product Design teams.
• Partner with CTO to ensure product and technology strategy evolve together.
• Drive AI-powered capabilities and innovation across the product.

Skills

Strategic thinking

Executive communication

Stakeholder management

API platforms

Cross-functional leadership

AI product strategy

Job description

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. They will understand the complexity of building mission-critical financial products where customer experience, regulatory 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.

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.
• Balance innovation, customer requests, regulatory requirements, 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.

Shape AI-Powered Products

• Define Trolley's long term AI product strategy.
• Identify opportunities to embed AI throughout the customer journey.
• Prioritize AI capabilities that improve onboarding, fraud detection, compliance, reporting, customer support, operational efficiency, and user productivity.
• Partner closely with the CTO to bring AI-powered capabilities to market.
• Ensure AI features deliver measurable customer value while maintaining responsible and secure AI practices.

Lead Product Management & Design

• Build, develop, and lead world class Product Management and Product Design teams.
• Establish product operating rhythms, roadmap planning processes, and product governance.
• Create a culture centered on customer obsession, accountability, innovation, collaboration, and execution.
• Recruit, mentor, and develop exceptional product leaders.
• Define success metrics that measure product adoption, customer satisfaction, retention, expansion, and business impact.

Customer & Market Leadership

• Serve as the executive team voice of the customer.
• Build strong relationships with strategic customers, partners, and industry stakeholders.
• Maintain deep expertise across fintech, payments, embedded finance, financial infrastructure, and regulatory trends.
• Translate customer feedback, industry developments, and competitive insights into product strategy.
• Partner closely with Sales, Marketing, and Customer Success on pricing, packaging, positioning, product launches, and customer adoption.

Executive Leadership

• Serve as a trusted advisor to the CEO and Board on product strategy, customer needs, market opportunities, and competitive positioning.
• Partner closely with the CTO to ensure product strategy and technology strategy evolve together.
• Contribute to company-wide strategic planning and operational excellence.
• Represent Trolley with customers, partners, investors, analysts, and industry events.
• Help shape the future direction of the company as a member of the Executive Leadership Team.

What We’re Looking For

Required Experience

• 10+ years of progressive product leadership experience, including leading Product Management organizations.
• Experience as a Chief Product Officer, VP Product, SVP Product, VP Product Management or equivalent executive within a high growth fintech, payments, financial infrastructure, embedded finance, or banking technology company.
• Demonstrated experience building and scaling enterprise B2B products within the payments ecosystem is required.
• Deep understanding of payment processing, cross border payments, money movement, payment operations, financial APIs, and platform based software products.
• Proven experience defining product strategy and delivering products that drive measurable customer and business outcomes.
• Experience building products within highly regulated environments where compliance, security, privacy, and reliability are essential.
• Strong experience partnering with Engineering organizations to deliver complex, API first software platforms.
• Demonstrated success leading cross functional organizations through rapid growth and organizational change.
• Proven ability to recruit, develop, and retain high performing Product Management and Product Design teams.
• Exceptional strategic thinking, executive communication, and stakeholder management skills.

Preferred Experience

• Experience with payout infrastructure, payment orchestration, merchant services, or embedded finance.
• Experience building products involving tax reporting, KYC/KYB, fraud prevention, identity verification, treasury, or financial operations.
• Experience leading enterprise API platforms.
• Experience launching AI-powered customer-facing products.
• Experience scaling globally distributed product organizations.

What We Offer

• Join an amazing team of diverse people working together on a common mission.
• Competitive salary & annual Leadership bonus.
• ESOP Program: Meaningful equity and ownership that aligns your success with ours.
• Extended healthcare benefits from Day 1.
• 4 weeks paid vacation per year + public holidays (+1 extra vacation day per year of service).
• 30 days remote work from anywhere.
• Gym membership allowance.
• 1/2 day Fridays off during summer.
• Company-provided use of Apple MacBook Pro and Mac gear.