Job Title

Were on a mission to modernize insurancemaking it simpler, more accessible, and customerfirst. The insurance industry is a $1T market thats remained largely untouched by the digital revolution, and PolicyMe is here to change that. As a remotefirst, Torontobased startup with big ambitions, were looking for a product leader to help us build the future of insurance in Canadaand beyond. Were now seeking a Principal Product Manager to lead and scale our Health Insurance business. This product leadership role will have endtoend 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. Principal Product Manager Location Ontario Description What youll 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 longterm 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 deeplyyou 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 help your team progress toward the longterm vision. Drive EndtoEnd Execution and Delivery: While youll shape the big picture, its not just delegatingyou wont 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 havent been solved before in Canada. Ensure we build the right things, the right way, at the right timebalancing shortterm wins with longterm 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 bestinclass 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 wellscoped, appropriately sized, and resilient. Coordinate gotomarket with Growth, CS, and Operations, ensuring launches are operationally ready and wellsupported. 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 drisk larger bets. Partner with Data to build dashboards, analyze performance, and translate results into next stepsincluding when to pivot, double down, or sunset work. What were looking for 8+ years of extensive product management experience in similar roles. Track record of success in growing D2C digital products and building bestinclass experiences. Nice to have experience in fintech or insurtech; but not required. Experience scaling products and product teams at highgrowth companiese.g., Series AD startups or techforward incumbents. Proven ability to develop and communicate a product vision that inspires both internal teams and external stakeholders. Strong business acumenyou understand how product connects to revenue, operations, customer success, and compliance. Comfortable leading through ambiguity and structuring ambiguous problems into measurable outcomes. Datadriven decisionmaker 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 missiondriven team culture. Why join us Generous PTO20 vacation days. A comprehensive benefits plan with premiums paid in full by PolicyMe. Investment in your professional developmentincluding an L&D budget, AI tooling budget, performance reviews twice a year and ongoing feedback to ensure you reach your highest potential. An extremely highperforming, lowego, remotefirst team that is truly disrupting an old industry. Option to work from home or our Torontobased office (bonus: we cover the costs to bring all our employees inperson twice a year for experiential socials!). Access to stock options based on performance. About PolicyMe At PolicyMe, we are Canadas 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 $10billion in insurance coverage to Canadians. Additional Notes Job Vacancy: This role reflects growth in our team and expanded operational scope. Were hiring to support increasing demand and continue delivering an exceptional customer experience. Commitment to Equal Opportunity: PolicyMe is an equalopportunity 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. Job type Remote job Tags manager design technical support growth financial fintech leader strategy management lead operational health engineering digital nomad #J-18808-Ljbffr