Principal Product Manager
Job Description
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 portfolioEstablish OKRs that helps your team progress towards the long-term versionDrive 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 CanadaEnsure 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 iterationCollaborate closely with Product Design to build best-in-class customer experiencesWrite clear, actionable product specs that connect business goals, customer needs, and technical constraintsPartner closely with engineering management to ensure initiatives are well-scoped, appropriately sized, and resilientCoordinate go-to-market with Growth, CS, and Operations, ensuring launches are operationally ready and well-supportedMeasurement, Experimentation and Iteration:Define success metrics and measurement plans for each initiative, including impact on funnel conversion, loss ratios, LTV, and operational efficiencyDesign and run experiments (e.g. A/B tests) to validate hypotheses and derisk larger betsPartner with Data to build dashboards, analyze performance, and translate results into next steps - including when to pivot, double down, or sunset workWhat we are looking for
8+ years of extensive product management experience in similar rolesTrack 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 daysA comprehensive benefits plan with premiums paid in full by PolicyMeInvestment 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 potentialAn extremely high performing, low-ego, remote-first team that is truly disrupting an old industryOption 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