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

Define & Own the Product Vision

Evolve our product 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 how customers discover new products of ours to how they manage it post-sale.
Build and champion a roadmap that balances innovation, operational excellence, and long-term scalability.
Develop a deep understanding of customer and operational pain points, using those insights to shape strategy and prioritization.
Establish clear OKRs and success metrics that align teams around measurable business and customer outcomes.

Solve Ambiguous Problems

Take open-ended, unstructured problems and break them down into clear opportunities, strategic priorities, and executable plans.
Bring creative, first-principles thinking to solve complex challenges that have not been solved before 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 organization.

Drive End-to-end Execution and Delivery

Lead the product team through the full product lifecycle: problem definition, discovery, solution design, scoping, execution, launch, and iteration.
While you’ll shape the strategic direction, you’re also highly execution-oriented and willing to dive into the details when needed.
Ensure we build the right things, the right way, at the right time by 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 closely with Growth, Customer Success, Operations, and other stakeholders to ensure launches are operationally ready and well-supported.
Drive alignment across teams and act as the connective tissue between stakeholders with competing priorities.

Measurement, Experimentation and Iteration

Define success metrics and measurement frameworks for all major initiatives, including customer 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 closely with Data to build dashboards, analyze 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 prioritization.

What we are looking for

8+ years of product management experience, including experience owning and scaling customer-facing digital products in high-growth environme

Principal Product Manager, Accounts & Automation at PolicyMe