Head of Insurance Solutions

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Banking & Finance πŸ‡¨πŸ‡¦ Oakville, Ontario - Canada 16 Oct 2026

Role overview

Geotab is seeking a Head of Insurance Solutions to lead the strategy and execution of insurance products that connect fleet data with carrier partnerships. As a global leader in IoT and connected transportation, Geotab processes billions of data points daily to help businesses optimize fleet operations, enhance safety, and achieve regulatory compliance. In this role, you will own the customer-facing insurance offering and drive measurable outcomes for both fleets seeking premium savings and Geotab’s carrier relationships.

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Key responsibilities

  • Develop and own the product vision, strategy, and roadmap for Insurance Solutions, including carrier partnership strategy and delivery standards that drive program adoption, customer retention, and monthly recurring revenue.
  • Prioritize fleet operator, manager, and driver needs by building a demand-driven roadmap, defining customer experience metrics, and optimizing the end-to-end insurance journey while ensuring compliance with data-sharing, privacy, and regulatory requirements.
  • Build and mentor a high-performing team across product, design, and engineering, starting as a hands-on leader and scaling capacity as the program grows while managing resource trade-offs and interim borrowed capacity.
  • Act as business owner for Insurance Solutions by translating board-level strategy into execution, managing the investment portfolio, leading annual planning, and reporting revenue contribution and growth trajectory to executive leadership.
  • Partner with platform teams, segment domain leads, peer solution leads, and go-to-market teams to align dependencies, package integrated solutions, and champion a company-first mindset across the organization.
  • Establish and maintain strategic relationships with board leadership by originating and evolving insurance strategy grounded in partnership growth and revenue impact, and making commercial investment cases for resourcing and market expansion.

Requirements

  • Ten to twelve years of overall experience, including at least ten years in product management, product engineering, or a related customer-facing product role.
  • Five or more years in senior product leadership roles with cross-functional organizational scope.
  • Five to eight years of leadership experience, including experience leading small teams or operating as a hands-on product leader who influences without direct authority, plus three or more years accountable for customer-facing outcomes and cross-functional coordination.
  • Bachelor’s degree in Business, Computer Science, Engineering, or a related field, or an equivalent combination of education and relevant work experience.
  • Deep domain knowledge in usage-based insurance, telematics data sharing, carrier and aggregator ecosystems, underwriting, risk scoring, and data privacy and regulatory considerations.
  • Strong commercial instincts, product leadership capability, and P&L literacy with expertise navigating the insurance, telematics, and insurtech landscape.
  • Demonstrated customer empathy, high accountability, excellent stakeholder management, and hands-on product orientation.

What makes this role worth considering

Geotab is a certified Great Place to Work with a fast-paced, inclusive environment where talented individuals work together to drive innovation and impact. This role offers the opportunity to scale a critical business function within a global technology leader, working across diverse teams and building strategic partnerships that shape the future of fleet insurance.

How to apply

Use the Apply button to view the official job posting and submit your application on Geotab's careers site.

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