Principal Product Manager, Accounts & Automation

About This Opportunity

We are representing a confidential Canadian insurtech organization seeking a Principal Product Manager to join their Accounts & Automation team. This is a remote-first opportunity based in Canada, ideal for a strategic product leader who can drive vision while executing hands-on across complex initiatives.

Our client is modernizing a traditional industry through digital-first customer experiences. This role will own multiple critical areas including multi-product adoption strategy, digital trust-building across offerings, and internal tooling to streamline operations.

Responsibilities

• Define and evolve product strategy to improve customer retention, operational efficiency, and cross-product adoption across the platform
• Develop a compelling long-term vision for simplifying insurance experiences, from product discovery through post-sale management
• Build and champion a roadmap balancing innovation, operational excellence, and scalability
• Establish clear OKRs and success metrics that align teams around measurable business and customer outcomes
• Take open-ended, unstructured problems and break them down into clear opportunities and executable plans
• Lead the product team through the full lifecycle: problem definition, discovery, solution design, execution, launch, and iteration
• Write clear product specifications connecting business goals, customer needs, operational requirements, and technical constraints
• Coordinate across Growth, Customer Success, Operations, and other stakeholders to ensure operationally-ready launches
• Define measurement frameworks for major initiatives including engagement, conversion, retention, and operational efficiency
• Design and run experiments to validate hypotheses and accelerate learning
• Partner with Data teams to build dashboards, analyze performance, and translate insights into action

What We're Looking For

• 8+ years of product management experience, including owning and scaling customer-facing digital products in high-growth environments
• Strong track record leading complex cross-functional initiatives and delivering measurable business and customer outcomes
• Experience building both customer-facing D2C products and operational/internal tooling
• 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 compelling product vision that aligns teams around long-term outcomes
• Strong business acumen with 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 managing competing priorities and maintaining momentum
• Excellent collaboration and stakeholder management skills with high emotional intelligence
• Strong documentation and communication skills across executives, engineers, designers, marketers, and operational stakeholders
• Highly analytical and data-driven, comfortable defining metrics, building measurement frameworks, and conducting analyses

How We Work With You

When you apply through Get A Job.ai, our talent team will review your application and conduct an initial screening to understand your background and career goals. If there's a strong match, we'll submit your profile to our client for consideration. We ask that you do not contact the client directly, as we manage the introduction process to ensure the best outcome for all parties.

Our recruiters will guide you through each stage, provide interview preparation support, and advocate on your behalf throughout the process.

Pay

Compensation details will be discussed during the screening process based on experience and qualifications.

Get A Job.ai is an equal opportunity recruiter. We welcome applicants of all backgrounds and provide fair consideration regardless of race, color, religion, sex, sexual orientation, gender identity, national origin, age, or disability. If you require accommodations during the application process, please let us know.