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Principal Product Manager, Accounts & Automation (Remote)

PolicyMe · Remote in Toronto

Extracted from the posting

Base
Not stated
Remote
Remote-first culture; Toronto-based company
Stack
AWS, LangChain, LangGraph, n8n (company stack)

Principal Product Manager owning product strategy and roadmap for the Accounts & Automation team at PolicyMe, a Toronto-based digital insurance company. The role covers multi-product adoption, digital customer trust, and accounts and internal tooling, reporting to the VP of Product and working with Engineering, Design, Growth, Operations, Customer Success and Data.

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 are now seeking a Principal Product Manager to join our Accounts & Automation team within our product organization. This role will own several areas of scope, including:

  • Defining the strategy and roadmap to make us the go-to provider for all of our customers’ personal insurance needs, including the platform-wide programs and features that drive multi-product adoption
  • Building trust digitally across the products we offer, so customers feel similar levels of confidence and reassurance as they would get when they speak with one our licensed advisors
  • Evolving our accounts product and internal tools to streamline operations and deliver a seamless customer experience end to end.

This is a highly strategic and hands-on leadership role that blends product vision, analytical thinking, structured execution, and cross-functional leadership. You will be responsible for shaping long-term product direction while also driving day-to-day execution across multiple complex initiatives. Reporting to the VP of Product, you will work closely with leaders across Engineering, Design, Growth, Operations, Customer Success, and Data to build products that create exceptional customer outcomes and drive meaningful business impact.

What you'll be doing

    What we are looking for

      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

      About PolicyMe:

      At PolicyMe, we are Canada’s leading digital insurance solution, offering straightforward and affordable financial protection for families from coast to coast. Our product suite includes Life Insurance, Critical Illness Insurance, and Health & Dental Insurance, all tailored to Canadians' evolving needs. We also offer B2B2C solutions, partnering with organizations to provide seamless digital insurance options. Founded by a team of insurance experts and technology entrepreneurs, PolicyMe is committed to making insurance simpler and more accessible. Since our launch in 2018, we have grown exponentially, selling over $10 billion in insurance coverage to Canadians.

      We are proud of the team we’ve built and are excited for those that are yet to join us. We operate with a remote-first culture, attracting top talent from across Canada. If you’re looking for a fast-paced, collaborative environment, working alongside incredibly ambitious yet humble humans, we may be the right place for you! To learn more, visit

      www.policyme.com

      .

      Additional Notes:

      Additional Notes:

      - Job Vacancy:

      This role reflects growth in our team and expanded operational scope. We’re hiring to support increasing demand and continue delivering an exceptional customer experience.

      - Commitment to Equal Opportunity:

      PolicyMe is an equal opportunity employer. We welcome applicants of all backgrounds and provide fair consideration regardless of race, colour, religion, sex, sexual orientation, gender identity, national origin, or disability.

      - Accessibility Statement:

      We are committed to providing an accessible hiring experience. If you require accommodations during the application process, please indicate this in the “Additional Information” section of your application.

      We thank all applicants for their interest, however, only those selected for an interview will be contacted.

      Company stack

      This posting doesn’t list technologies. These are the ones PolicyMe uses across its other roles.

      AWSLangChainLangGraphn8nPostgreSQLPythonReactRedux
      PolicyMe
      PolicyMe

      Job details

      TypeFull-time
      Work ModeRemote
      LevelLead
      Location🇨🇦Toronto, ON
      PostedNov 06, 2026
      Apply Now