Jobs at Trolley (Now Hiring) — 11 open

Chief Technology Officer (CTO)

Location: Toronto, Ontario (Hybrid) or Montréal, Québec (Hybrid) 

Reports to: CEO

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 will be heavily investing in AI to accelerate product innovation, improve operational efficiency, and transform how software is built across the company. We are seeking a Chief Technology Officer (CTO) to lead our technology organization and help define how AI shapes the future of Trolley.

The Opportunity

The CTO will be a key member of Trolley's executive leadership team, responsible for defining and executing the company's technology strategy while ensuring the scalability, security, reliability, and innovation of our platform.

A critical mandate for the successful candidate will be driving AI adoption across the engineering team and broader company. We are looking for a leader who has successfully implemented AI powered development practices, enabled organization wide adoption, and delivered measurable improvements in engineering productivity, software quality, and speed of execution.

The CTO will oversee Engineering and Information Security while partnering closely with Product, Operations, Finance, Compliance, and GTM leaders to align technology investments with company objectives.

What You’ll Do

Define and Execute Trolley's Technology Strategy

• Define and execute Trolley's long term technology vision and roadmap.
• Partner with the CEO and executive leadership team to align technology investments with company strategy and growth objectives.
• Ensure the platform remains scalable, secure, reliable, and capable of supporting Trolley's continued global expansion.
• Evaluate emerging technologies and identify opportunities to create competitive advantage and improve operational efficiency.
• Lead architectural decisions that support long term product innovation and business growth.

Lead AI Transformation Across the Organization

• Define and execute Trolley's AI strategy across Engineering and the broader organization.
• Drive adoption of AI powered software development practices, coding assistants, testing automation, QA automation, observability, and operational tooling.
• Establish measurable improvements in engineering productivity, software quality, and delivery velocity through AI.
• Identify opportunities to leverage AI within products, customer experiences, internal operations, and decision making processes.
• Build a culture of continuous learning and responsible AI adoption.
• Serve as Trolley's executive leader for AI innovation.

Lead and Scale Engineering

• Build, develop, and lead a high performing engineering team.
• Establish a culture of accountability, ownership, collaboration, and technical excellence.
• Recruit, mentor, and retain exceptional engineering leaders and talent.
• Implement scalable engineering processes, operating rhythms, and performance metrics.
• Ensure consistent delivery of secure, reliable, and high quality software.

Oversee Information Security

• Lead Trolley's Information Security strategy and function, with the Head of InfoSec.
• Ensure strong security, privacy, and risk management practices across the organization.
• Maintain robust cybersecurity controls, incident response capabilities, and business continuity planning.
• Partner with Compliance and Risk teams to support customer requirements, audits, certifications, and regulatory obligations.
• Foster a security first culture while enabling innovation and speed.

Executive Leadership

• Serve as a trusted advisor to the CEO and Board on technology, AI, cybersecurity, and innovation.
• Contribute to company wide strategic planning and operational excellence.
• Represent Trolley with customers, partners, investors, and industry stakeholders when appropriate. 
• 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 technology leadership experience, including experience leading large engineering organizations.
• Experience as a CTO, VP Technology, VP Engineering, SVP Engineering, or equivalent senior technology executive within a high-growth SaaS, fintech, payments, marketplace, or technology company.
• Demonstrated success implementing AI powered engineering practices and driving meaningful adoption across software development teams.
• Proven track record of delivering measurable productivity, quality, and execution improvements through AI enabled development.
• Deep understanding of modern software architecture, cloud infrastructure, distributed systems, and platform scalability.
• Experience leading technology organizations through periods of significant growth and organizational change.
• Experience overseeing Information Security programs and cybersecurity strategy.
• Strong track record of recruiting, developing, and retaining world-class technical talent.

Preferred Experience

• Experience in fintech, payments, financial infrastructure, or regulated software environments.
• Experience leading AI transformation initiatives beyond engineering teams.
• Familiarity with modern AI development tooling, agentic workflows, automation platforms, and emerging AI technologies.
• Experience scaling globally distributed platforms and engineering teams

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.

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