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About the Role

PolicyMe is seeking a Principal Product Manager to join their Accounts & Automation team. This role will define strategy and roadmaps for customer needs, build digital trust across products, and evolve accounts and internal tools for a seamless customer experience. It's a strategic and hands-on leadership position blending product vision, analytical thinking, and cross-functional leadership, reporting to the VP of Product.

Responsibilities

Define and own the product vision, evolving product strategy to improve customer delight, retention, referral growth, operational efficiency, and cross-product adoption.
Develop a compelling long-term vision for simplifying insurance for Canadians.
Build and champion a roadmap balancing innovation, operational excellence, and long-term scalability.
Develop a deep understanding of customer and operational pain points to shape strategy and prioritization.
Establish clear OKRs and success metrics aligned with business and customer outcomes.
Solve ambiguous, unstructured problems by breaking them down into clear opportunities, strategic priorities, and executable plans.
Apply creative, first-principles thinking to complex challenges in the Canadian insurance market.
Balance customer needs, technical constraints, operational realities, and business priorities in product decisions.
Lead through ambiguity and create clarity for teams and stakeholders.
Drive the full product lifecycle: problem definition, discovery, solution design, scoping, execution, launch, and iteration.
Ensure the right things are built the right way, at the right time, balancing short-term wins with long-term investments.
Collaborate with Product Design and Engineering to build best-in-class customer and internal product experiences.
Write clear, actionable product specifications connecting business goals, customer needs, operational requirements, and technical constraints.
Coordinate 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.
Define success metrics and measurement frameworks for all major initiatives.
Design and run experiments to validate hypotheses, de-risk investments, and accelerate learning.
Partner with Data to build dashboards, analyze product performance, and translate insights into actionable next steps.
Use data, customer insights, and business context to continuously refine strategy and prioritization.

Requirements

8+ years of product management experience, including 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.
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.

Skills

Product Vision
Roadmap Development
Customer Insights
Data Analysis
Experimentation
Stakeholder Management
AI Prototyping
D2C Product Development
Internal Tooling Development
Agile Methodologies
Cross-functional Leadership
Problem Solving
Prioritization
Communication
Documentation

Location

Toronto
Remote

Work Type

Remote-first
Full-time

Experience Level

Principal
8+ years

Benefits

Generous PTO (20 vacation days)
Comprehensive benefits plan with premiums paid in full
Investment in professional development (L&D budget, AI tooling budget)
Performance reviews twice a year
Ongoing feedback
Access to stock options based on performance

About the Company

PolicyMe is Canada’s leading digital insurance solution, offering straightforward and affordable financial protection.
Their product suite includes Life Insurance, Critical Illness Insurance, and Health & Dental Insurance, with B2B2C solutions.
Founded by insurance experts and technology entrepreneurs, PolicyMe aims to make insurance simpler and more accessible.
Since 2018, they have grown exponentially, selling over $10 billion in insurance coverage.
They operate with a remote-first culture, attracting top talent from across Canada.
The company fosters a fast-paced, collaborative environment with ambitious yet humble individuals.

Equal Opportunity

PolicyMe is an equal opportunity employer.
They welcome applicants of all backgrounds and provide fair consideration regardless of race, colour, religion, sex, sexual orientation, gender identity, national origin, or disability.
They are committed to providing an accessible hiring experience and accommodate applicants requiring accommodations during the application process.