Trolley

Chief Technology Officer

Montreal, Quebec · Exec

Sponsorship not specifiedDetected 1 day ago

Distributed SystemsCloud PlatformsCybersecurityIncident ResponseCanvaTest AutomationLeadershipCollaboration

About the role

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.

Partner with the CEO and executive leadership team to align technology investments with company strategy and growth objectives.
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
Drive adoption of AI powered software development practices, coding assistants, testing automation, QA automation, observability, and operational tooling.
Lead and Scale Engineering
Build, develop, and lead a high performing engineering team.
Implement scalable engineering processes, operating rhythms, and performance metrics.
Lead Trolley's Information Security strategy and function, with the Head of InfoSec.
Maintain robust cybersecurity controls, incident response capabilities, and business continuity planning.

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.
Proven track record of delivering measurable productivity, quality, and execution improvements through AI enabled development.
Experience leading technology organizations through periods of significant growth and organizational change.
Experience overseeing Information Security programs and cybersecurity strategy.
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

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).
Gym membership allowance.
Define and execute Trolley's long term technology vision and roadmap.
Build a culture of continuous learning and responsible AI adoption.

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 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.
The Opportunity
Define and Execute Trolley's Technology Strategy

This listing is sourced directly from Trolley's careers page and normalized into a canonical job model.