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’re now seeking a Principal Product Manager to lead and scale our Life and Critical Illness business. This product leadership role will have end-to-end ownership over the product vision, the strategy, and the execution of our Life and Critical Illness product roadmap. This is a pivotal role, reporting to the VP of Product and working closely with multiple teams across the organization.
What you'll be doing
- Evolve our product strategy to meet ambitious growth, retention, and customer impact goals that you will own.
- Set a compelling long-term product vision for our Life and Critical Illness vertical, aligned with business priorities and grounded in customer insights.
- Champion a roadmap that balances innovation with operational excellence.
- Understand your product and customer context deeply – you are comfortable building strong domain knowledge and being an expert in your category, which you can then apply to the vision for your portfolio.
- Establish OKRs that help your team progress towards the long-term vision. Drive End-to-end Execution and Delivery
- While you’ll shape the big picture, it’s not just delegating – you won’t hesitate to get your hands dirty; diving into product reviews, writing business cases, helping unblock teams, etc.
- Bring creative new ideas to solve complex problems that haven't been solved before in Canada.
- Ensure we build the right things, the right way, at the right time – balancing short-term wins with long-term platform evolution.
- Lead the product team through the full product lifecycle: problem definition, discovery, solution design, scoping, execution, launch, and iteration.
- 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, including impact on funnel conversion, LTV, and operational efficiency.
- Design and run experiments (e.g., A/B tests) to validate hypotheses and derisk 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're looking for
- 8+ years of extensive product management experience in similar roles.
- Track record of success in growing D2C digital products and building best-in-class experiences. Nice to have experience in fintech or insurtech; but not required.
- Experience scaling products and product teams at high-growth companies (e.g., Series A–D startups or tech-forward incumbents).
- Proven ability to develop and communicate a product vision that inspires both internal teams and external stakeholders.
- Strong business acumen – you understand how product connects to revenue, operations, customer success, and compliance.
- Comfortable leading through ambiguity and structuring ambiguous problems into measurable outcomes.
- Data-driven decision-maker with fluency in OKRs, KPIs, funnels, and experimentation.
- Adept at prioritizing tradeoffs, managing competing needs, and maintaining velocity without sacrificing quality, while demonstrating exceptionally strong operational discipline – reliably following through, closing loops quickly, and keeping stakeholders updated without being prompted.
- High emotional intelligence with a collaborative, transparent leadership style.
- Strong communicator who can tailor messages to executives, engineers, marketers, and everyone in between.
- Committed to building a diverse, inclusive, and mission-driven team culture.
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
What We Do
We are on a mission to put families first with simple and affordable insurance. We strongly believe that life insurance is fundamental to a sound financial plan. It ensures that your family can replace lost income to pay for key expenses, eliminate debt, pay for college, or address other financial goals in the unfortunate circumstance that you pass. However, we also understand that life insurance is complicated. There are many factors to take into account in determining how much life insurance is right for you, and what type of policy best suits your needs. That is why we believe life insurance advice should be transparent, customized and most importantly, convenient. We are an experienced team trying to change the insurance industry with a customer first approach. Our proprietary life insurance algorithm assesses your needs and recommends the best product for you – regardless of commission structure. Life insurance is complicated, and our advice engine can help you find the the best protection in the most cost-effective way
