Chief Technology Officer

Role overview

Trolley is building a borderless payouts infrastructure for the internet economy. Its platform and API help businesses pay creators, on-demand workers, and suppliers around the world, while also automating payout operations, collecting tax and banking details, and reducing fraud and risk.

Used by hundreds of businesses including Canva, Soundcloud, and Envato, the company has processed millions of payments globally. As Trolley expands, it is investing heavily in AI to speed up product innovation, strengthen operations, and change how software is developed across the business.

The organization is hiring a Chief Technology Officer to lead the technology function and shape the role AI will play in Trolley’s future.

Location and reporting

This executive role is based in Toronto, Ontario or Montréal, Québec in a hybrid setup. It reports directly to the CEO and sits at the executive / C-suite level.

Key responsibilities

The CTO will guide the company’s technology direction, oversee engineering and information security, and work closely with leaders across Product, Operations, Finance, Compliance, and GTM to make sure technology choices support business goals.

• Set Trolley’s long-term technology vision and turn it into an actionable roadmap.
• Work with the CEO and executive team to align technology investments with growth plans and company strategy.
• Keep the platform scalable, dependable, secure, and ready for global expansion.
• Assess new technologies and identify opportunities to improve efficiency and create competitive advantage.
• Make architectural decisions that support product innovation and long-term business growth.
• Lead the company’s AI strategy across engineering and the wider organization.
• Promote AI-enabled development methods, including coding assistants, testing automation, QA automation, observability, and operational tooling.
• Set targets and measure gains in engineering productivity, software quality, and delivery speed through AI adoption.
• Find ways to apply AI to products, customer experiences, internal workflows, and decision-making.
• Build a culture of continuous learning and responsible use of AI.
• Serve as the executive sponsor for AI innovation.
• Grow and lead a high-performing engineering organization.
• Create a team culture grounded in accountability, ownership, collaboration, and technical excellence.
• Recruit, coach, and retain strong engineering leaders and technical talent.
• Put scalable engineering processes, operating cadences, and performance metrics in place.
• Ensure software delivery remains secure, reliable, and high quality.
• Oversee the information security function with the Head of InfoSec.
• Maintain strong privacy, security, and risk management practices across the company.
• Strengthen cybersecurity controls, incident response readiness, and business continuity planning.
• Work with Compliance and Risk teams to support customer needs, audits, certifications, and regulatory obligations.
• Encourage a security-first culture without slowing innovation.
• Advise the CEO and Board on technology, AI, cybersecurity, and innovation matters.
• Contribute to company-wide strategic planning and operational excellence.
• Represent Trolley with customers, partners, investors, and industry stakeholders when needed.
• Help shape the company’s future as a senior executive leader.

Experience and qualifications

The ideal candidate brings at least 10 years of increasing technology leadership experience, including leadership of large engineering organizations. Prior experience as a CTO, VP Technology, VP Engineering, SVP Engineering, or another equivalent senior technology role in a high-growth SaaS, fintech, payments, marketplace, or technology business is expected.

The role requires a strong history of putting AI-powered engineering practices into action and driving broad adoption across development teams, with clear gains in productivity, quality, and execution. Deep knowledge of modern software architecture, cloud infrastructure, distributed systems, and platform scaling is essential.

The successful candidate should also have experience leading technology groups through rapid growth and organizational change, managing information security programs and cybersecurity strategy, and building world-class technical teams.

Preferred background

• Previous experience in fintech, payments, financial infrastructure, or regulated software environments.
• Experience extending AI transformation beyond engineering teams.
• Familiarity with modern AI development tools, agentic workflows, automation platforms, and newer AI technologies.
• Experience scaling globally distributed platforms and engineering teams.

Compensation and benefits

• Competitive salary with an annual leadership bonus.
• ESOP participation with meaningful equity and ownership.
• Extended health coverage starting on day one.
• Four weeks of paid vacation each year, plus public holidays, and one additional vacation day for every year of service.
• Thirty days of remote work from anywhere.
• Gym membership allowance.
• Half-day Fridays during the summer.
• Company-provided Apple MacBook Pro and related Mac equipment.

Who this role suits

This opportunity is best suited to senior technology leaders who have scaled engineering organizations, modernized software delivery with AI, and helped guide security-conscious, high-growth product businesses.

Additional details

The role is part of a mission-driven company focused on enabling global payouts at scale. The executive will be expected to collaborate across departments and contribute to company-wide strategy, operational execution, and long-term innovation.