Principal Product Manager, Accounts & Automation (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 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.

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.

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:

 

- 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.