Principal Product Manager, Accounts – Automation

This is a fully remote position, open to applicants in Canada.

📋 Description

• Define and Own the Product Vision

• - Advance our product strategy to enhance customer satisfaction, retention, referral growth, operational efficiency, and cross-product adoption.

• - Create an engaging long-term vision for simplifying insurance for Canadians, from how customers discover our products to how they manage them after purchase.

• - Develop and advocate for a roadmap that balances innovation, operational excellence, and scalable growth.

• - Gain a thorough understanding of customer and operational challenges, leveraging these insights to guide strategy and prioritization.

• - Set clear OKRs and success metrics that unite teams around measurable business and customer objectives.

• Solve Ambiguous Problems

• - Deconstruct open-ended, unstructured issues into distinct opportunities, strategic priorities, and actionable plans.

• - Utilize creative, first-principles thinking to address complex challenges that remain unsolved in the Canadian insurance sector.

• - Weigh customer needs, technical limitations, operational realities, and business priorities when making product-related decisions.

• - Lead through uncertainty and establish clarity for teams and stakeholders throughout the organization.

• Drive End-to-end Execution and Delivery

• - Guide the product team through the complete product lifecycle: problem identification, discovery, solution design, scoping, execution, launch, and iteration.

• - While you will influence the strategic direction, you will also be highly execution-oriented and ready to delve into details when necessary.

• - Ensure we develop the right products, in the right manner, at the right time by balancing immediate gains with long-term platform investments.

• - Collaborate closely with Product Design and Engineering to create exceptional customer and internal product experiences.

• - Draft clear, actionable product specifications that align business goals, customer needs, operational requirements, and technical limitations.

• - Work in close coordination with Growth, Customer Success, Operations, and other stakeholders to ensure launches are operationally prepared and adequately supported.

• - Foster alignment across teams and serve as the glue between stakeholders with competing priorities.

• Measurement, Experimentation and Iteration

• - Establish success metrics and measurement frameworks for all significant initiatives, encompassing customer engagement, funnel conversion, retention, operational efficiency, and long-term customer value.

• - Design and conduct experiments to validate hypotheses, minimize risks for larger investments, and expedite learning.

• - Collaborate closely with Data to create dashboards, analyze product performance, and translate insights into actionable next steps, including decisions on when to pivot, invest further, or discontinue initiatives.

• - Employ data, customer insights, and business context to continually refine strategy and prioritization.

⛳️ Requirements

• 8+ years of product management experience, including a background in owning and scaling customer-facing digital products in high-growth settings.

• Proven success in leading complex cross-functional initiatives and achieving measurable business and customer results.

• Experience in developing both customer-facing D2C products and operational/internal tooling products.

• Familiarity with building prototypes utilizing AI.

• Experience in scaling products and product practices within high-growth startups or dynamic technology organizations.

• Demonstrated ability to articulate and communicate a compelling product vision that aligns teams and stakeholders towards long-term goals.

• Strong business acumen with a comprehensive understanding of how product decisions influence revenue, operations, customer success, retention, and compliance.

• Exceptional talent for structuring ambiguous challenges and transforming them into clear, actionable strategies.

• Strong operational discipline with the capability to manage competing priorities, maintain momentum, and consistently follow up with stakeholders.

• Excellent collaboration and stakeholder management skills, characterized by high emotional intelligence and a transparent leadership approach.

• Strong documentation and communication abilities - adept at tailoring messages effectively for executives, engineers, designers, marketers, and operational stakeholders.

• Comfortable leading initiatives with numerous moving parts and fostering alignment across multiple teams.

• Strong prioritization skills and the ability to define MVP scope while balancing speed, quality, and long-term scalability.

• Highly analytical and data-driven, with proficiency in working with product data, defining metrics, establishing measurement frameworks, and performing analyses to guide decisions.

🏝️ Benefits

• Generous PTO - 20 vacation days

• A comprehensive benefits package with premiums fully covered by PolicyMe

• Commitment to your professional growth, including an L&D budget, AI tooling budget, biannual performance reviews, and ongoing feedback to help you reach your fullest potential

• An exceptionally high-performing, low-ego, remote-first team that is genuinely disrupting an outdated industry

• Flexibility to work from home or our Toronto office (bonus: we cover costs for all employees to meet in-person twice a year for experiential social events!)

• Access to stock options based on performance