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Role Description

The Senior Product Manager is accountable for driving client retention outcomes across our Requoting product area. You will own the US Requoting product through its initial market launch and scale Canadian Requoting to serve our growing customer base. This role combines 0-to-1 product development for the US market with scaling an established product in Canada. You will execute on product area strategy, lead discovery programs, and drive execution that directly impacts broker retention rates and operational efficiency. You will report to our Lead Product Manager and partner closely with engineering, design, implementation, and customer success to ship value in consistent cycles. Your success will be measured by successful scaling of our US Requoting product, not feature completion.

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.

Qualifications

• 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.
• 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.
• Move with urgency: We default to acting fast and with urgency.
• Be curious: We understand the world by being curious and asking why.
• Excellence in execution: What separates good from great is a high level of execution.
• Act like an owner: We're all owners of the business and act like it.
• Fight for simplicity: We believe there is sophistication in simplicity.

Compensation and Benefits

• $140,000 - $160,000 a year
• Base pay: $140,000-$160,000 CAD for Vancouver-based candidates, dependent on experience and performance.
• Employee stock options based on experience level.
• Comprehensive health benefits, including Lifestyle Spending Account.
• Four weeks of paid vacation per year.
• Work anywhere in the world for 60 days of the year.
• Parental leave top-ups: 6 months for birthing parents, 8 weeks for non-birthing parents (up to $100,000 annual salary).
• Enhanced mental health benefits through Dialogue, providing unlimited access to mental health practitioners at no cost.