Principal Product Manager at PolicyMe

The insurance industry is a massive, trillion-dollar market that has remained largely unchanged by the digital revolution for far too long. At PolicyMe, we are on a mission to change that by making insurance simpler, more accessible, and truly customer-first. Since our launch in 2018, we have grown rapidly and already provided over $10 billion in coverage to families across Canada. We are a remote-first team of insurance experts and tech entrepreneurs who believe in building products that actually help people. If you are looking to join a fast-paced, collaborative environment alongside ambitious and humble colleagues, we would love to meet you.

The opportunity

We are looking for a Principal Product Manager to lead and scale our Life and Critical Illness business. In this pivotal role, you will have end-to-end ownership of the product vision, strategy, and execution for this vertical. You will report directly to our VP of Product and work cross-functionally to ensure our offerings continue to meet the evolving needs of Canadians. This is a chance to shape the future of a category that touches millions of lives.

A day in the life

• You will set a compelling long-term product vision for our Life and Critical Illness vertical, establishing clear OKRs and roadmaps that balance innovation with operational excellence.
• You will lead the full product lifecycle, from initial problem definition and discovery to solution design, launch, and iterative improvements.
• You will partner with our data and engineering teams to design experiments, analyze performance metrics, and translate those insights into actionable next steps for the business.

Who you are

You are a seasoned product leader with over 8 years of experience, ideally within high-growth startups or tech-forward companies. You have a proven track record of scaling digital products and possess the business acumen to connect product decisions to revenue and operational success. You are comfortable leading through ambiguity and can communicate effectively with everyone from engineers to executive stakeholders. You are data-driven, highly organized, and committed to fostering a diverse and inclusive team culture. Fluency in English is required for this role.

Why you'll love it here

We offer a remote-first culture that gives you the flexibility to work from anywhere, though you are always welcome to join us at our Toronto office. We are dedicated to your success and well-being, providing a comprehensive package that includes:

• A comprehensive medical and dental insurance plan with premiums paid in full by us.
• 20 days of paid time off.
• Significant investment in your professional development through learning budgets, AI tooling support, and regular performance feedback.
• Access to stock options based on performance.
• The opportunity to join a high-performing, low-ego team that meets in person twice a year for experiential socials.