Principal Product Manager

PolicyMe

13d • Remote

About The Position

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.

Requirements

• 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.
• 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.

Nice To Haves

• Nice to have experience in fintech or insurtech; but not required.

Responsibilities

• 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.

Benefits

• 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 This Job Offers

• Job Type: Full-time
• Career Level: Principal
• Education Level: No Education Listed
• Number of Employees: 11-50 employees