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 Policy Me 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.

• 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.

• 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.

• Generous PTO - 20 vacation days.
• A comprehensive benefits plan with premiums…