Senior Director, Product Management

Overview of the role: We’re on a mission to modernize insurance - making it simpler, more accessible, and customer-first. The insurance industry is a $1T market that’s remained largely untouched by the digital revolution, and PolicyMe is here to change that. As a remote-first, Toronto-based startup with big ambitions, we’re looking for a product leader to help us build the future of insurance in Canada - and beyond. We’re now seeking a Senior Director of Product Management to scale our product organization and take end-to-end ownership of the product vision, strategy, and execution across new and existing product lines. This is a pivotal role, reporting to the VP of Product and working closely with multiple teams across the organization. What you’ll be doing: Define & Lead the Product Vision: Evolve our product strategy to meet ambitious growth, retention, and customer impact goals that you will own. Set a compelling long‑term product vision, aligned with business priorities and grounded in customer insights. Champion a roadmap that balances innovation with operational excellence. Understand your product and customer context deeply - you are comfortable building strong domain knowledge and being an expert in your category, which you can then apply to the vision for your portfolio Bring creative new ideas to solve complex problems that haven't been solved before in Canada Establish OKRs that help your teams progress towards the long‑term version While you’ll shape the big picture, it’s not just delegating - you won’t hesitate to get hands‑on; diving into product reviews, writing business cases, helping unblock teams, etc. Other duties as required Scale the Product Function: Build, lead, and coach high‑performing product teams (PMs, designers, etc.). Foster a product‑led culture rooted in experimentation, impact, and user empathy. Drive Strategic Product Development: Oversee full lifecycle development of improvements to existing insurance products and net‑new offerings in the future. Partner with Engineering, Growth, and CS to define go‑to‑market strategies and deliver frictionless customer experiences. Ensure we build the right things, the right way, at the right time - balancing short‑term wins with long‑term platform evolution. What we are looking for: 8+ years of progressive product management experience, including at least 4+ years in a Sr. leadership role. Track record of success in B2C or D2C digital products — nice to have experience in fintech or insurtech; but not required. Experience scaling products and product teams at high‑growth companies (e.g., Series A-D startups or tech‑forward incumbents). Proven ability to develop and communicate a product vision that inspires both internal teams and external stakeholders. Experience managing and growing high‑performing teams while balancing execution and coaching. Strong business acumen — you understand how product connects to revenue, operations, customer success, and compliance. Comfortable leading through ambiguity and structuring ambiguous problems into measurable outcomes. Data‑driven decision‑maker with fluency in OKR’s, KPIs, funnels, and experimentation. Adept at prioritizing tradeoffs, managing competing needs, and maintaining velocity without sacrificing quality. High emotional intelligence with a collaborative, transparent leadership style. Strong communicator who can tailor messages to executives, engineers, marketers, and everyone in between. Committed to building a diverse, inclusive, and mission‑driven team culture. Why join us: Generous PTO — 20 vacation days Access to stock options and a comprehensive benefits plan A remote‑first team with company paid, in‑person socials and the option to work from our Toronto‑based office Resources to help your professional development, including an L&D budget, performance reviews twice a year and ongoing feedback to ensure you reach your highest potential Work with an empathetic, high‑performing team in a flexible, results‑oriented environment About PolicyMe: At PolicyMe, we are Canada’s leading digital insurance solution, offering straightforward and affordable financial protection for families from coast to coast. Our product suite includes Life Insurance, Critical Illness Insurance, and Health & Dental Insurance, all tailored to Canadians' evolving needs. We also offer B2B2C solutions, partnering with organizations to provide seamless digital insurance options. Founded by a team of insurance experts and technology entrepreneurs, PolicyMe is committed to making insurance simpler and more accessible. Since our launch in 2018, we have grown exponentially, selling over $10 billion in insurance coverage to Canadians. We are proud of the team we’ve built and are excited for those that are yet to join us. We operate with a remote‑first culture, attracting top talent from across Canada. If you’re looking for a fast‑paced, collaborative environment, working alongside incredibly ambitious yet humble humans, we may be the right place for you To learn more, visit www.policyme.com. Commitment to Equal Opportunity: PolicyMe is proud to be an equal opportunity employer. All applicants will be considered for employment without attention to race, colour, religion, sex, sexual orientation, gender identity, national origin, or disability status. We thank all applicants for their interest, however, only those selected for an interview will be contacted. Accessibility Statement: PolicyMe is dedicated to ensuring an accessible experience for all candidates. If you require accommodations during the application process, please let us know in the "Additional Information" section of the job application. We are committed to working with you to provide support and make reasonable adjustments throughout the process. #J-18808-Ljbffr