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 Staff Product Manager to join as a leader in our product function. This role will own our post-sale customer experience, our customer account product and critical internal facing products that power how our company operates.
It is a high-impact role that blends analytical thinking, structured execution, and strong collaboration.
What you'll be doing
Shape our Product Vision:Evolve our product strategy to improve how our post-sale experience delivers greater customer delight, retention, referral growth and cross-product adoption.Partner with leadership to develop a compelling vision for how our accounts platform can evolve and set a new standard for how Canadians manage insurance.Bring the vision to life by building and championing a product roadmap that balances innovation and operational excellence.Solve Ambiguous Problems:Develop a deep understanding of both PolicyMe customers and internal customers - use this knowledge to build products and features that your users love.Take open-ended, unstructured problems and break them down into clearly defined bodies of work.Come up with creative solutions to solve our most complex problems.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 iterationEnsure we build the right things, the right way, at the right time - balancing short-term wins with long-term platform evolution.Collaborate closely with Product Design to build best-in-class 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 well-scoped, appropriately sized, and resilient.Coordinate go-to-market with Growth, CS, and Operations, ensuring launches are operationally ready and well-supported.Measurement, Experimentation and Iteration:Define success metrics and measurement plans for each initiative.Design and run experiments to validate hypotheses and de-risk larger bets.Partner with Data to build dashboards, analyze performance, and translate results into next steps — including when to pivot, double down, or sunset work.
What we are looking for
Relevant product experience: You have 4-6 years of experience in product management, with experience building customer-facing D2C products and exposure to internal-facing products. You can speak to your track record of leading projects and delivering measurable results.
Exceptional collaboration skills: You have high emotional intelligence and can "be the glue" between many different stakeholders in the organization.
Strong documentation skills: You write clear, concise, and well-informed product specifications/requirements.
Ability to structure ambiguous problems: You have the ability to take an ambiguous problem and structure it. You are someone who can start with an idea and manage it from concept to deployment.
Demonstrated experience leading: You are comfortable bringing people together, leading teams and managing projects with many moving parts. You have a sense of ownership and are excited about driving a project from start to finish.
Strong communication: You know how to tailor your communication style to meet different audiences. You know when to lead conversations, but also when to listen. You know how to set expectations with different stakeholders and when to ask these stakeholders for help. You can take a complex topic and explain it succinctly in an easy-to-understand manner.
A strong sense for prioritization: You know how to prioritize different builds and define what is truly part of an MVP to optimize developer productivity. You know how to balance agile market feedback with our customers' product expectations.
Curiosity and comfort with technical topics: While you do not need a technical background, you are naturally curious about how everything works. You know when to ask clarifying questions and are not shy about diving into complex topics.
An analytical mindset: You are comfortable working with product data, defining its structure and running analyses to answer key questions.
Why join us
Generous PTO - 20 vacation daysA comprehensive benefits plan with premiums paid in full by PolicyMeInvestment 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 potentialAn extremely high performing, low-ego, remote-first team that is truly disrupting an old industryOption 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 $160,000–$180,000 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:
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.
