Principal Product Manager - Accounts & Automation

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