Associate VP, Product

Summary

Join PolicyMe, a Toronto-based InsurTech startup, as an Associate VP of Product Management. Scale our product organization and take ownership of the product vision, strategy, and execution across new and existing product lines. Define and lead the product vision, evolving our strategy to meet ambitious growth goals. Build, lead, and coach high-performing product teams. Oversee the full lifecycle development of existing and new insurance products. Partner with various teams to define go-to-market strategies and deliver seamless customer experiences. This pivotal role reports to the VP of Product and requires strong leadership, strategic thinking, and data-driven decision-making.

Requirements

• 8+ years of progressive product management experience, including at least 4+ years in a Sr. leadership role
• 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

Responsibilities

• 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 portfolioBring creative new ideas to solve complex problems that haven't been solved before in CanadaEstablish OKRs that help your teams progress towards the long-term versionWhile 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
• 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

Preferred Qualifications

Track record of success in B2C or D2C digital products - nice to have experience in fintech or insurtech; but not required

Benefits

• 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