Associate VP of Product Management

Employment Type: Full-time

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Position Overview

PolicyMe is on a mission to modernize the insurance industry, making it simpler, more accessible, and customer-first. As a remote-first, Toronto-based startup, we are seeking a product leader to help us build the future of insurance in Canada and beyond.

We are looking for an Associate VP 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.

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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.
• Develop strong domain knowledge and become an expert in your category to inform 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 vision.
• Be hands-on, diving into product reviews, writing business cases, and helping unblock teams.

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 the full lifecycle development of improvements to existing insurance products and net-new offerings.
• Partner with Engineering, Growth, and Customer Success 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.

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Requirements

• 8+ years of progressive product management experience, including at least 4+ years in a Senior leadership role.
• Track record of success in B2C or D2C digital products. Experience in fintech or insurtech is a plus, 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 – understanding 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 OKRs, 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.

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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.

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