policyme - Principal Product Manager, Accounts & Automation
Requirements
• 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.
Responsibilities
• 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.
Benefits
• 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
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