Principal Product Manager, Accounts & Automation

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 are now seeking a Principal Product Manager to join our Accounts & Automation team within our product organization. This role will own several areas of scope, including: • Defining the strategy and roadmap to make us the go-to provider for all of our customers’ personal insurance needs, including the platform-wide programs and features that drive multi-product adoption • Building trust digitally across the products we offer, so customers feel similar levels of confidence and reassurance as they would get when they speak with one our licensed advisors • Evolving our accounts product and internal tools to streamline operations and deliver a seamless customer experience end to end. This is a highly strategic and hands-on leadership role that blends product vision, analytical thinking, structured execution, and cross-functional leadership. You will be responsible for shaping long-term product direction while also driving day-to-day execution across multiple complex initiatives. Reporting to the VP of Product, you will work closely with leaders across Engineering, Design, Growth, Operations, Customer Success, and Data to build products that create exceptional customer outcomes and drive meaningful business impact. What you’ll be doing Define & Own the Product Vision • Evolve our product strategy to improve customer delight, retention, referral growth, operational efficiency, and cross-product adoption. • Develop a compelling long-term vision for how to make insurance simple for Canadians, from how customers discover new products of ours to how they manage it post-sale. • Build and champion a roadmap that balances innovation, operational excellence, and long-term scalability. • Develop a deep understanding of customer and operational pain points, using those insights to shape strategy and prioritization. • Establish clear OKRs and success metrics that align teams around measurable business and customer outcomes. Solve Ambiguous Problems • Take open-ended, unstructured problems and break them down into clear opportunities, strategic priorities, and executable plans. • Bring creative, first-principles thinking to solve complex challenges that have not been solved before in the Canadian insurance market. • Balance customer needs, technical constraints, operational realities, and business priorities when making product decisions. • Lead through ambiguity and create clarity for teams and stakeholders across the organization. Drive End-to-end Execution and Delivery • Lead the product team through the full product lifecycle: problem definition, discovery, solution design, scoping, execution, launch, and iteration. • While you’ll shape the strategic direction, you’re also highly execution-oriented and willing to dive into the details when needed. • Ensure we build the right things, the right way, at the right time by balancing short-term wins with long-term platform investments. • Collaborate closely with Product Design and Engineering to build best-in-class customer and internal product experiences. • Write clear, actionable product specifications that connect business goals, customer needs, operational requirements, and technical constraints. • Coordinate closely with Growth, Customer Success, Operations, and other stakeholders to ensure launches are operationally ready and well-supported. • Drive alignment across teams and act as the connective tissue between stakeholders with competing priorities. Measurement, Experimentation and Iteration • Define success metrics and measurement frameworks for all major initiatives, including customer engagement, funnel conversion, retention, operational efficiency, and long-term customer value. • Design and run experiments to validate hypotheses, de-risk larger investments, and accelerate learning. • Partner closely with Data to build dashboards, analyze product performance, and translate insights into actionable next steps – including when to pivot, double down, or sunset initiatives. • Use data, customer insights, and business context to continuously refine strategy and prioritization. What we are looking for • 8+ years of product management experience, including experience owning and scaling customer-facing digital products in high-growth environments. • Strong track record of leading complex cross-functional initiatives and delivering measurable business and customer outcomes. • Experience building both customer-facing D2C products and operational/internal tooling products. • Experience building prototypes with AI. • Experience scaling products and product practices within high-growth startups or fast-moving technology organizations. • Proven ability to define and communicate a compelling product vision that aligns teams and stakeholders around long-term outcomes. • Strong business acumen with a deep understanding of how product decisions impact revenue, operations, customer success, retention, and compliance. • Exceptional ability to structure ambiguous problems and turn them into clear, actionable plans. • Strong operational discipline with the ability to manage competing priorities, maintain momentum, and consistently close loops with stakeholders. • Excellent collaboration and stakeholder management skills with high emotional intelligence and a transparent leadership style. • Strong documentation and communication skills – able to tailor messaging effectively across executives, engineers, designers, marketers, and operational stakeholders. • Comfortable leading initiatives with many moving parts and driving alignment across multiple teams. • Strong sense of prioritization and ability to define MVP scope while balancing speed, quality, and long-term scalability. • Highly analytical and data-driven, with comfort working with product data, defining metrics, building measurement frameworks, and conducting analyses to inform decisions. 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 Compensation Additional Information 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: 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.