Head of Legal

We are Trader, a Canadian leader in digital automotive solutions. Our flagship brands — AutoTrader.ca, AutoSync, Dealertrack Canada and CMS — help Canadians buy, sell, and finance vehicles with confidence. As part of AutoScout24 group, Europe’s largest online car marketplace, we’re shaping the future of automotive retail in Canada and beyond.

We are seeking a Head of Legal, Canada to lead and scale our Canadian legal function within a fast-growing marketplace and fintech business. This is a senior, hands-on role for a pragmatic legal leader who thrives close to the business, enjoys solving complex regulatory and commercial challenges, and can balance strategic oversight with day-to-day execution.

Reporting to the Global General Counsel, you will serve as the primary legal advisor for Canada, enabling business growth while proactively managing legal and regulatory risk.

What You'll Do

• Lead all legal matters for Canadian operations and align local execution with global legal strategy.
• Lead a team of two paralegals and a data privacy coordinator.
• Advise on marketplace, fintech, payments, consumer protection, privacy, and financial services regulations.
• Partner cross-functional to deliver practical, commercially focused legal guidance.
• Draft and negotiate key commercial agreements, including partnerships, vendors, and technology contracts.
• Oversee regulatory engagement, compliance frameworks, disputes, and external counsel management.
• Serving as a trusted advisor to senior leadership.

What You'll Need

• 3+ years of legal experience, including substantial experience in technology, marketplace, fintech, or financial services environments.
• Qualified to practice law in Canada and in good standing with a Canadian law society.
• Strong knowledge of Canadian consumer protection, payments, fintech, privacy, and regulatory frameworks.
• Proven ability to operate as both a strategic leader and hands-on advisor in fast-paced, high-growth environments.
• Commercially minded, solutions-oriented, and skilled at simplifying complex legal issues for senior stakeholders.
• Confident, collaborative leader with the ability to influence executive decision-making.

Join us on our journey as we bring together the best of Europe and North America to shape the future of automotive retail.

The base salary range for this position is CAD $175,000 – $225,000.

This range reflects the expected compensation at the time of posting. The final offer may vary and can be higher based on relevant skills, experience, location, and market conditions. Based on the role, the total rewards package may also include benefits, bonus, and other employee offerings.

Use of Artificial Intelligence in Hiring: We use artificial intelligence (“AI”) in our hiring process, including to screen, assess, or select applicants for this position. Vacancy Status: This job posting is for an existing vacancy.