Remote Principal Product Manager

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

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