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. 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. 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. 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.

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. 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.

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. 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. ~ 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. ~ Excellent collaboration and stakeholder management skills with high emotional intelligence and a transparent leadership style. ~ 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. Generous PTO - 20 vacation days Investment in your career 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 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. We operate with a remote‑first culture, attracting top talent from across Canada. We’re hiring to support increasing demand and continue delivering an exceptional customer experience.

- We welcome applicants of all backgrounds and provide fair consideration regardless of race, colour, religion, sex, sexual orientation, gender identity, national origin, or disability. -

📌 Principal Product Manager, Accounts & Automation (Remote) (Winnipeg)
🏢 Lever
📍 Winnipeg