Associate VP, Product (Remote)

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