Principal Product Manager (Remote)

Overview of the role:
We’re on a mission to modernize insurance - making it simpler, more accessible, and customer-first. The insurance industry is a $1T market that’s remained largely untouched by the digital revolution, and PolicyMe is here to change that. As a remote-first, Toronto-based startup with big ambitions, we’re looking for a product leader to help us build the future of insurance in Canada - and beyond.

We’re now seeking a Principal Product Manager to lead and scale our Health Insurance business. This product leadership role will have end-to-end ownership over the product vision, the strategy, and the execution of our health insurance product roadmap. This is a pivotal role, reporting to the VP of Product and working closely with multiple teams across the organization.

What you'll be doing:
• Define & Own the Product Vision:
• Evolve our product strategy to meet ambitious growth, retention, and customer impact goals that you will own.
• Set a compelling long-term product vision for our health insurance vertical, aligned with business priorities and grounded in customer insights.
• Champion a roadmap that balances innovation with operational excellence.
• Understand your product and customer context deeply - you are comfortable building strong domain knowledge and being an expert in your category, which you can then apply to the vision for your portfolio
• Establish OKRs that helps your team progress towards the long-term version
• Drive End-to-end Execution and Delivery:
• While you’ll shape the big picture, it’s not just delegating - you won’t hesitate to get your hands dirty; diving into product reviews, writing business cases, helping unblock teams, etc.
• Bring creative new ideas to solve complex problems that haven't been solved before in Canada
• Ensure we build the right things, the right way, at the right time - balancing short-term wins with long-term platform evolution.
• Lead the product team through the full product lifecycle: problem definition, discovery, solution design, scoping, execution, launch, and iteration
• Collaborate closely with Product Design to build best-in-class customer experiences
• Write clear, actionable product specs that connect business goals, customer needs, and technical constraints
• Partner closely with engineering management to ensure initiatives are well-scoped, appropriately sized, and resilient
• Coordinate go-to-market with Growth, CS, and Operations, ensuring launches are operationally ready and well-supported
• Measurement, Experimentation and Iteration:
• Define success metrics and measurement plans for each initiative, including impact on funnel conversion, loss ratios, LTV, and operational efficiency
• Design and run experiments (e.g. A/B tests) to validate hypotheses and derisk larger bets
• Partner with Data to build dashboards, analyze performance, and translate results into next steps - including when to pivot, double down, or sunset work

What we are looking for:
• 8+ years of extensive product management experience in similar roles
• Track record of success in growing D2C digital products and building best-in-class experiences. Nice to have experience in fintech or insurtech; but not required.
• Experience scaling products and product teams at high-growth companies (e.g., Series A-D startups or tech-forward incumbents).
• Proven ability to develop and communicate a product vision that inspires both internal teams and external stakeholders.
• Strong business acumen - you understand how product connects to revenue, operations, customer success, and compliance.
• Comfortable leading through ambiguity and structuring ambiguous problems into measurable outcomes.
• Data-driven decision-maker with fluency in OKRs, KPIs, funnels, and experimentation.
• Adept at prioritizing tradeoffs, managing competing needs, and maintaining velocity without sacrificing quality.
• High emotional intelligence with a collaborative, transparent leadership style.
• Strong communicator who can tailor messages to executives, engineers, marketers, and everyone in between.
• Committed to building a diverse, inclusive, and mission-driven team culture.

Why join us:
• Generous PTO - 20 vacation days
• A comprehensive benefits plan with premiums paid in full by PolicyMe
• Investment in your professional development, including an L&D budget, AI tooling budget, performance reviews twice a year and ongoing feedback to ensure you reach your highest potential
• An extremely high performing, low-ego, remote-first team that is truly disrupting an old industry
• Option to work from home or our Toronto-based office (bonus: we cover the costs to bring all our employees in-person twice a year for experiential socials!)
• Access to stock options based on performance

About PolicyMe:
At PolicyMe, we are Canada’s leading digital insurance solution, offering straightforward and affordable financial protection for families from coast to coast. Our product suite includes Life Insurance, Critical Illness Insurance, and Health & Dental Insurance, all tailored to Canadians' evolving needs. We also offer B2B2C solutions, partnering with organizations to provide seamless digital insurance options. Founded by a team of insurance experts and technology entrepreneurs, PolicyMe is committed to making insurance simpler and more accessible. Since our launch in 2018, we have grown exponentially, selling over $10 billion in insurance coverage to Canadians.

We are proud of the team we’ve built and are excited for those that are yet to join us. We operate with a remote-first culture, attracting top talent from across Canada. If you’re looking for a fast-paced, collaborative environment, working alongside incredibly ambitious yet humble humans, we may be the right place for you! To learn more, visit www.policyme.com.

Additional Notes:
- Job Vacancy: This role reflects growth in our team and expanded operational scope. We’re hiring to support increasing demand and continue delivering an exceptional customer experience.
- Commitment to Equal Opportunity: PolicyMe is an equal opportunity employer. We welcome applicants of all backgrounds and provide fair consideration regardless of race, colour, religion, sex, sexual orientation, gender identity, national origin, or disability.
- Accessibility Statement: We are committed to providing an accessible hiring experience. If you require accommodations during the application process, please indicate this in the “Additional Information” section of your application.

We thank all applicants for their interest, however, only those selected for an interview will be contacted.