Policyme

Principal Product Manager

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Job Description

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

Define & Own the Product Vision

  • 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

    • Apply Now
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