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PolicyMe · 2 days ago

Principal Product Manager

United States

Full-time

Remote

Lead/Staff

8+ years exp

PolicyMe is Canada’s leading digital insurance solution, and they are seeking a Principal Product Manager to lead and scale their Health Insurance business. This role involves end-to-end ownership over the product vision, strategy, and execution of the health insurance product roadmap, working closely with multiple teams across the organization.

FinanceInsuranceInsurTechLife Insurance

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 health insurance 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 helps your team progress towards the long-term version

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, loss ratios, 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

Qualification

Product managementD2C digital productsProduct vision developmentData-driven decision-makingOKRsKPIsCommunicatorCollaborative leadershipHigh emotional intelligence

Required

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

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

Preferred

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

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