Senior Product Manager, Requoting

What You'll Do

• Product Roadmap Ownership: Execute on the Requoting product area strategy by translating strategic direction into explicit hypotheses linking product changes to client retention metrics. Balance customer value, business impact, and technical considerations across US and Canadian markets. Maintain a rolling roadmap that reflects discovery learnings and outcome priorities.
• Discovery and Validation: Design and execute discovery programs that inform outcome-focused roadmaps. Identify non-obvious customer needs through direct research with brokers. Ensure prototype validation before engineering commitment. Connect problems to measurable retention and efficiency outcomes.
• Solution Definition: Define solution approaches for complex, ambiguous problems in insurance requoting workflows. Make sound scope tradeoffs that optimize for outcome learning. Evaluate AI-first approaches where they accelerate broker efficiency or improve quote accuracy.
• Cross-Functional Leadership: Influence product direction through data and compelling outcome-based arguments. Drive alignment across engineering, design, implementation, and customer success toward shared retention goals. Create transparency about priorities, tradeoffs, and progress. Partner with Implementation to ensure product decisions account for broker onboarding complexity and BMS integration requirements.
• Go-to-Market Execution: Own ongoing US market go-to-market iteration, building on our initial launch foundation. Partner with Marketing and Enablement to refine positioning and customer communications based on market feedback. Iterate rapidly when outcomes are not met.
• Measurement and Iteration: Own Requoting product area metrics with accountability for improvement. Design measurement frameworks that connect feature usage to client retention. Identify root causes when outcomes fall short. Maintain 30-day shipping cycles with continuous learning loops.

The right person for this role will have:

• 5-7 years of product management experience with proven track record of shipping products that drive measurable business outcomes in fast-paced environments
• Experience owning a product area end-to-end, including discovery, execution, and outcome accountability
• Demonstrated ability to launch new products (0-to-1) or scale early-stage products with ambiguous requirements and limited historical data
• Strong discovery skills with experience running customer research that uncovers root problems rather than surface requests
• Ability to define and prioritize based on outcome hypotheses, not feature requests
• Experience influencing cross-functional teams without direct authority
• Comfort with data analysis and ability to design measurement frameworks that connect product changes to business outcomes
• Excellent communication skills with ability to create transparency about priorities and tradeoffs for technical and non-technical audiences
• Bias toward action with comfort operating in ambiguous environments and making decisions with imperfect information
• Comfort with AI-first prototyping tools and workflows (e.g., Replit, Lovable, Make, Claude Code) for rapid solution exploration and validation
Bonus points if you have
• Experience in insurance, fintech, or other regulated industries with complex B2B workflows (candidates without insurance experience should expect a 3-6 month domain learning curve)
• Experience with multi-market products (US/Canada or similar)
• Familiarity with broker management systems or insurance agency operations
• Previous experience at high-growth, venture-backed companies


Location
• We strongly prefer candidates based in Vancouver, where you'll work from our Olympic Village office three days per week. For the right candidate, we're open to remote arrangements within the US or Canada, with a requirement to travel to Vancouver at least once per quarter for team collaboration.


Why This Role Matters
• Client retention is existential for insurance brokerages. When a policyholder leaves, the broker loses recurring revenue and the relationship built over years. Requoting transforms how brokers proactively identify at-risk clients and take action before it's too late. You will own a product area that directly impacts whether our customers keep their clients. Every percentage point of improved retention translates to meaningful revenue for brokerages and better outcomes for the policyholders they serve. This role offers the rare combination of launching a new market (US) while scaling proven value (Canada), with clear metrics that tie your work to customer success.


Our Guiding Principles
• Customers at the core. We put the customer at the center of all we do. We don't take what customers say blindly, but think critically and build what they need. Customers are the core of everything we do, and our business exists to serve them.
• Move with urgency. We default to acting fast and with urgency. We slow down when necessary, but this should be a deliberate choice. This principle fights the lethargy that comes with growth.
• Be curious. We understand the world by being curious and asking why. We aren't satisfied with surface-level understanding and seek deeper knowledge. Don't take someone's word for it or accept "because that's how we do it."
• Excellence in execution. What separates good from great is a high level of execution. We commit ourselves to excellence in everything we do, from delivering an amazing product to writing a great email.
• Act like an owner. We're all owners of the business and act like it. We follow through on commitments, own our results, and think long-term.
• Fight for simplicity. Systems evolve to become more complex over time. We believe there is sophistication in simplicity; we intentionally fight for streamlined solutions and are committed to the uncomplicated.