Chief of staff Jobs in Toronto, ON

Are you ready to be a big part of something big?

At Trader Interactive, we make buying and selling a great experience. We’re a group of go-getters who decided they didn’t want to settle for the status quo. We come together as one team to build value and drive innovation across our industries - but we have fun while we do it and make sure our people are always our #1 priority.

When it comes to your career, we want to provide big opportunities to help you make a big impact. But for this to be possible, we strive to feel small. Small enough to quickly change tack, small enough to learn from different teams and small enough to connect authentically with leadership.

What We Offer

• An inclusive and supportive work environment where you can move your career forward and will have the chance to do work that has real, significant impact on the world.

• The opportunity to be a part of a global group of digital marketplace businesses (CAR Group) located across Australia, Brazil, Chile and South Korea - collectively we have around 2,500 team members worldwide, and our CAR Group Tour means you might just find yourself working in one of those businesses sometime soon.

• Plenty of flexible leave options and employee benefits including up to 31 days of paid time off in your first year, continuing education with access to LinkedIn Learning, a full benefits package including medical, dental & vision, 401K with company match, and wellness program.

What You’ll Do

Trader Interactive powers some of the leading digital marketplaces in North America across RV, marine, powersports, and commercial equipment. As a fast-growing technology company delivering consistent double-digit growth, our platforms serve millions of users and play a critical role in connecting buyers and sellers across our markets.

Following years of growth and acquisition, we are investing in a full platform transformation to simplify our architecture, accelerate engineering velocity, and unlock the next generation of marketplace capabilities, including AI-driven experiences.This role is central to that transformation.

As CTO, you will lead the modernization of our technology ecosystem and build a high-performing global engineering organization capable of delivering scalable, reliable, and data-driven platforms that power our next phase of growth.

Technology Strategy and Platform Transformation

• Define and execute the long-term technology strategy across all marketplace platforms.

• Lead platform simplification and modernization across frontend, backend, and data architecture.

• Reduce technical debt and eliminate legacy systems created through acquisition.

• Align with broader CAR Group architecture and shared services where appropriate.

Engineering Execution and Delivery

• Improve engineering velocity, delivery predictability, and execution discipline.

• Establish modern development practices, including AI-assisted tooling.

• Drive consistency across frameworks, platforms, and teams.

Platform Reliability, Performance, and Scale

• Ensure high availability, performance, and scalability of consumer-facing platforms.

• Implement best-in-class observability, monitoring, and incident response.

• Maintain systems where uptime and performance directly impact revenue.

Data and AI Enablement

• Build a unified, high-integrity data platform powering search, analytics, and customer insight.

• Enable AI-driven capabilities across search, pricing, recommendations, and lead optimization.

• Treat data as a core product asset.

Security and Trust

• Lead cybersecurity and platform protection in partnership with CAR Group.

• Ensure protection of customer data, marketplace integrity, and platform availability.

Leadership

• Lead a global engineering organization across multiple regions.

• Build a culture of accountability, operational excellence, and high performance.

• Partner closely with the CEO, Chief Product Officer, and executive team.

What We’re Looking For

Experience

• 15+ years in technology leadership, including senior engineering leadership roles.

• Experience scaling consumer-facing digital platforms with millions of users.

• Proven track record leading large, global engineering organizations.

• Experience driving platform modernization and reducing technical complexity.

• History of improving engineering velocity and delivery outcomes.

Technical Expertise

• Distributed systems and cloud-native architecture (AWS).

• Modern web and application stacks (e.g., Node.js, PHP, React, Vue).

• Data platforms and search technologies (e.g., Elasticsearch, NoSQL, relational databases).

• DevOps and site reliability practices.

• Experience with AI-enabled development and product capabilities.

Leadership

• Strong operator with a bias for execution and outcomes.

• Ability to simplify complex systems and organizations.

• Strategic thinker with hands-on leadership capability.

• Builder of high-performing, accountable teams.

So come and join our team - because every role is a big role in our plans to go big.

TI proudly supports a diverse workforce, and we encourage candidates from underrepresented groups to apply. Trader Interactive is an equal opportunity