Principal Product Manager, Accounts & Automation (Remote)

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 Staff Product Manager to join as a leader in our product function. This role will own our post-sale customer experience, our customer account product and critical internal facing products that power how our company operates.

It is a high-impact role that blends analytical thinking, structured execution, and strong collaboration.

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 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 fast-moving technology organizations.
• Proven ability to define and communicate a compelling product vision that aligns teams and stakeholders around long-term outcomes.
• Strong business acumen with a 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 prioritization 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.

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