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PolicyMePO

Principal Product Manager

PolicyMe is a Canadian digital insurance provider offering life, critical illness, and health & dental insurance through a streamlined online platform, focused on affordability and accessibility.

PolicyMe

Employee count: 51-200

Canada only

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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.

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.

Benefits

  • Generous Paid Time Off - 20 vacation days
  • Comprehensive benefits plan with premiums paid in full by PolicyMe
  • Investment in your professional development
  • Access to stock options based on performance

About the job

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Job type

Full Time

Experience level

Location requirements

Hiring timezones

Canada +/- 0 hours

About PolicyMe

Learn more about PolicyMe and their company culture.

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PolicyMe is revolutionizing the Canadian insurance landscape through groundbreaking technology and a steadfast commitment to customer-centric innovation. Founded in 2018 by a team of insurance experts and technology entrepreneurs, PolicyMe is dedicated to making insurance simpler, more accessible, and affordable for all Canadians. The company leverages a sophisticated digital platform to streamline the traditionally complex and often opaque process of obtaining insurance. This technology-first approach allows PolicyMe to offer a seamless, end-to-end online experience, from personalized advice and quote comparison to policy application and issuance, often in a matter of minutes rather than weeks. By significantly reducing inefficiencies and operational costs, PolicyMe consistently provides more affordable coverage options without compromising on quality or protection.

At the core of PolicyMe's innovative model is its proprietary technology that automates many aspects of the life insurance value chain. This includes advanced data analytics and an AI-driven infrastructure to enhance underwriting processes, optimize customer touchpoints, and personalize the insurance journey. PolicyMe offers a comprehensive suite of products, including Term Life Insurance, Critical Illness Insurance, and Health & Dental Insurance, all tailored to meet the evolving needs of Canadian families. The company is not only focused on direct-to-consumer offerings but also provides robust B2B2C solutions, partnering with leading financial institutions and organizations to embed its digital insurance platform, thereby expanding access to millions more Canadians. This dual approach, combined with a commitment to transparency and human support when needed, positions PolicyMe at the forefront of the AI-driven transformation in the insurance industry, striving to close coverage gaps and ensure every Canadian has access to the financial protection they deserve.

Employee benefits

Learn about the employee benefits and perks provided at PolicyMe.

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Stock options

Eligible employees have access to stock options.

Remote-first team

The company operates with a remote-first culture.

Performance reviews twice a year

Performance reviews are conducted twice annually.

Company paid, in-person socials

PolicyMe organizes company-paid in-person social events.

View PolicyMe's employee benefits
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PolicyMe

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