Principal Product Manager - Remote Eligible

Principal Product Manager

This is a high-impact leadership opportunity for an experienced product professional passionate about transforming digital customer experiences within a rapidly evolving industry. The role focuses on leading the vision, strategy, and execution of innovative Life and Critical Illness insurance products while driving measurable business growth and customer value. You will work at the intersection of technology, operations, data, and customer experience, collaborating closely with cross-functional teams to shape scalable and customer-centric solutions. This position offers end-to-end ownership of a critical product portfolio, from defining long-term strategy to overseeing execution, experimentation, and optimization initiatives. Ideal candidates thrive in fast-paced environments, enjoy solving complex challenges, and are comfortable balancing strategic thinking with hands-on product leadership. The role also provides the opportunity to contribute directly to the modernization of a traditionally underserved industry through digital innovation and operational excellence.

Accountabilities:

• Define and lead the long-term product vision and strategy for the Life and Critical Illness portfolio, ensuring alignment with business objectives and customer needs.
• Build and manage a product roadmap that balances innovation, operational efficiency, customer experience, and long-term platform scalability.
• Drive the full product lifecycle, including discovery, problem definition, solution design, prioritization, development, launch, measurement, and iteration.
• Collaborate closely with Product Design, Engineering, Data, Operations, Growth, and Customer Success teams to deliver high-quality digital experiences.
• Translate customer insights, business objectives, and technical constraints into clear and actionable product requirements and specifications.
• Lead experimentation and optimization initiatives, including A/B testing, funnel analysis, and performance measurement to improve conversion, retention, and operational efficiency.
• Establish and monitor OKRs, KPIs, and success metrics to evaluate product impact and guide strategic decision-making.
• Partner with engineering leadership to ensure product initiatives are properly scoped, technically resilient, and delivered efficiently.
• Coordinate go-to-market execution and operational readiness for new product launches and feature enhancements.
• Provide leadership through ambiguity, proactively solving complex business and product challenges while maintaining alignment across stakeholders.

Requirements:

• 8+ years of experience in product management roles within digital, technology-driven, or high-growth environments.
• Proven success building and scaling direct-to-consumer digital products with strong customer engagement and business impact.
• Experience leading product strategy and execution within fast-growing startups or innovative technology organizations.
• Strong business acumen with the ability to connect product decisions to revenue growth, operational efficiency, customer success, and compliance considerations.
• Demonstrated ability to define and communicate compelling product visions that align teams and stakeholders around shared goals.
• Expertise in data-driven product management, including OKRs, KPIs, funnel analysis, experimentation, and performance optimization.
• Strong analytical and problem-solving skills with the ability to structure ambiguous challenges into measurable outcomes.
• Experience collaborating closely with cross-functional teams including Engineering, Design, Marketing, Operations, and Data.
• Excellent communication, stakeholder management, and leadership skills across technical and non-technical audiences.
• Highly organized with exceptional operational discipline, prioritization, and execution management capabilities.
• Collaborative leadership style with high emotional intelligence and a strong commitment to building inclusive and mission-driven teams.
• Experience within fintech, insurtech, or regulated industries is considered an advantage but is not required.

Benefits:

• Generous paid time off, including 20 vacation days annually.
• Comprehensive health benefits package with premiums fully covered.
• Remote-first work environment with flexibility to work from anywhere in Canada or from a Toronto-based office.
• Company-sponsored in-person team events and social gatherings throughout the year.
• Professional development support including learning and development budgets, AI tooling resources, and continuous performance feedback.
• Opportunity to work within a high-performing, collaborative, and low-ego team culture.
• Access to stock options based on performance and contribution.
• Exposure to impactful projects driving digital transformation within a rapidly growing industry.
• Strong focus on employee growth, innovation, collaboration, and work-life balance.