Product Manager (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 has 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 Manager to help us build the future of insurance in Canada and beyond.

In this role, you will own product execution for one of our core lines of business within Life & Critical Illness (LCI). You will work cross-functionally with engineering, design, and insurance experts to bring new features and products to life that directly improve customer experience and drive business growth. It is a high-impact role that blends analytical thinking, structured execution, and strong collaboration.

What you'll be doing::
• Own delivery and optimization of key product flows within Life & Critical Illness.
• Drive end-to-end execution of new product initiatives and define MVP scopes.
• Partner with engineering and design to build, test, and ship high-quality features.
• Work with insurance and compliance partners to translate complex rules into intuitive user experiences.
• Use data and customer insights to identify conversion levers, prioritize initiatives, and guide roadmap decisions.
• Balance short-term optimization with long-term product strategy and scalability.
• Lead discovery and experimentation processes to validate hypotheses and reduce risk.
• Collaborate with stakeholders to align product work with company-level goals and KPIs.

What we are looking for::
• While a minimum of 4 years of product management experience in a high-growth environment is ideal, we’re open to candidates who can demonstrate strong product thinking, an entrepreneurial mindset, and a track record of building new products or business models.
• Proven ability to execute and ship impactful features or products from concept to delivery.
• Analytical and data-informed mindset, with comfort using dashboards and metrics to guide prioritization.
• Experience working cross-functionally with design, engineering, and business stakeholders.
• Strong communicator and storyteller, able to craft compelling narratives to influence decisions across audiences. Experience at translating complex technical or business concepts - from engineers and designers to senior leaders and founders.
• Curiosity, initiative, and the ability to thrive in a fast-moving, ambiguous environment.
• Experience in fintech, Insurtech, or another regulated digital industry is considered an asset.
• Familiarity with SQL, experimentation frameworks, or analytics tools such as Looker or MixPanel.
• Strong product sense and commercial awareness of how product decisions impact growth and operations.
• Experience working in a startup or scale-up with high ownership expectations would be considered an asset.

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: The total target cash compensation for this role is $110,000 - $143,000 CAD, based on experience. We’ll walk through the details together during the interview.

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
- 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.