Overview
We’re on a mission to modernise 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.

Role Summary
We are seeking a Principal Product Manager to join our Accounts & Automation team within our product organisation. 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 programmes 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 of our licensed advisors.

Evolving our accounts product and internal tools to streamline operations and deliver a seamless customer experience end to end.

Key Responsibilities

Define and own the product vision, evolving strategy to improve customer delight, retention, referral growth, operational efficiency, and cross‑product adoption.

Develop a compelling long‑term vision for how to make insurance simple for Canadians, from discovery to post‑sale management.

Build and champion a roadmap that balances innovation, operational excellence, and scalability.

Develop a deep understanding of customer and operational pain points to shape strategy and prioritisation.

Establish clear OKRs and success metrics that align teams around measurable outcomes.

Take open‑ended problems and break them down into clear opportunities, strategic priorities, and executable plans.

Bring creative, first‑principles thinking to solve complex challenges in the Canadian insurance market.

Balance customer needs, technical constraints, operational realities, and business priorities when making product decisions.

Lead through ambiguity and create clarity for teams and stakeholders across the organisation.

Lead the product team through the full product lifecycle: problem definition, discovery, solution design, scoping, execution, launch, and iteration.

Ensure we build the right things, the right way, at the right time, balancing short‑term wins with long‑term platform investments.

Collaborate closely with Product Design and Engineering to build best‑in‑class customer and internal product experiences.

Write clear, actionable product specifications that connect business goals, customer needs, operational requirements, and technical constraints.

Coordinate with Growth, Customer Success, Operations, and other stakeholders to ensure launches are operationally ready and well‑supported.





Drive alignment across teams and act as connective tissue between stakeholders with competing priorities.

Define success metrics and measurement frameworks for major initiatives, including engagement, funnel conversion, retention, operational efficiency, and long‑term customer value.

Design and run experiments to validate hypotheses, de‑risk larger investments, and accelerate learning.

Partner with Data to build dashboards, analyse product performance, and translate insights into actionable next steps – including when to pivot, double down, or sunset initiatives.

Use data, customer insights, and business context to continuously refine strategy and prioritisation.

Qualifications

8+ years of product management experience, including owning and scaling customer‑facing digital products in high‑growth environments.

Strong track record of leading complex cross‑functional initiatives and delivering measurable business and customer outcomes.

Experience building both customer‑facing D2C products and operational/internal tooling products.

Experience building prototypes with AI.

Experience scaling products and product practices within high‑growth startups or rapid‑moving technology organisations.

Proven ability to define and communicate a compelling product vision that aligns teams and stakeholders around long‑term outcomes.

Strong business acumen with deep understanding of how product decisions impact revenue, operations, customer success, retention, and compliance.

Exceptional ability to structure ambiguous problems and turn them into clear, actionable plans.

Strong operational discipline with the ability to manage competing priorities, maintain momentum, and consistently close loops with stakeholders.

Excellent collaboration and stakeholder management skills with high emotional intelligence and a transparent leadership style.

Strong documentation and communication skills – able to tailor messaging effectively across executives, engineers, designers, marketers, and operational stakeholders.

Comfortable leading initiatives with many moving parts and driving alignment across multiple teams.

Strong sense of prioritisation and ability to define MVP scope while balancing speed, quality, and long‑term scalability.

Highly analytical and data‑driven, with comfort working with product data, defining metrics, building measurement frameworks, and conducting analyses to inform decisions.

Benefits





Generous PTO – 20 vacation days.

A comprehensive benefits plan with premiums paid in full by PolicyMe.

Investment in professional development, including an L&D; budget, AI tooling budget, biannual performance reviews, and ongoing feedback to help 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; we cover the costs of bringing all 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 organisations 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 who 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

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; only those selected for an interview will be contacted.

We may use artificial intelligence (AI) tools to support parts of the hiring process, such as reviewing applications, analysing resumes, or assessing responses. These tools assist our recruitment team but do not replace human judgement. Final hiring decisions are ultimately made by humans. If you would like more information about how your data is processed, please contact us.

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📌 Principal Product Manager, Accounts & Automation (Remote) (Ontario)
🏢 PolicyMe
📍 Ontario