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Oakville, Ontario, Canada
Hybrid
We are always looking for amazing talent who can contribute to our growth and deliver results! Geotab is seeking a Head of Insurance Solutions who will own the customer-facing insurance product and partnership outcome, connecting Geotab fleet data and safety solutions to insurers so that fleets earn measurable premium savings, and Geotab grows direct carrier relationships, insurance program adoption, and the retention of insurance-acquired customers. If you love technology, and are keen to join an industry leader — we would love to hear from you!
As a Head of Insurance Solutions, your key area of responsibility will be product strategy, roadmap, and outcome ownership; customer value delivery and external customer engagement; people leadership, development, and organizational health; business performance, investment prioritization, and KPA attainment; and cross-domain coordination and practitioner community participation.
You will need to work closely with platform domain teams as internal technical partners, Heads of Segment Domain as distribution partners, peer Heads of Solution Domain (Driver Risk & Safety, Driver Coaching, Altitude), Sales, Marketing, Alliances, and department board leadership. To be successful in this role, you will be a hands-on, product-oriented leader with deep customer empathy, high accountability, excellent stakeholder management, and a Geotab First mindset. In addition, the successful candidate will have strong commercial instincts, product leadership capability, P&L literacy, and expertise navigating the insurance, telematics, and insurtech landscape.
Drive Product Strategy & Outcome Ownership: Own the product vision, strategy, and roadmap for Insurance Solutions; lead carrier partnership strategy, make principled build/buy/partner decisions, and define delivery standards to drive key KPAs like program adoption, retention, active carrier partnerships, and program-attributed MRR.
Deliver Fleet Customer Value: Treat fleet operators, managers, and drivers as primary customers by prioritizing a demand-driven roadmap, defining customer experience metrics, optimizing the end-to-end insurance journey, and ensuring compliance with data-sharing consent, privacy, and regulatory requirements.
Lead & Scale People and Teams: Build and mentor a high-trust, customer-obsessed domain—starting as a hands-on leader and scaling product, design, and engineering capacity as program traction grows while managing interim borrowed capacity and resource trade-offs.
Manage Business Performance & Investment: Act as the business owner for Insurance Solutions outcomes by translating board-level strategy into execution, managing the investment portfolio, leading annual planning, and presenting revenue contribution and growth trajectory to executive leadership.
Coordinate Across Domains & Build Strategic Alliances: Partner with Platform and Segment Domain leads, peer Solution leads, and go-to-market teams to align dependencies, package solutions, leverage shared infrastructure, participate in discipline practitioner communities, and champion a "Geotab First" mindset.
Own Board Relationship & Accountability: Originate and evolve the insurance strategy grounded in partnership growth and revenue impact, make commercial investment cases for resourcing and market expansion, and build a strategic partnership with board leadership.
10–12 years of relevant experience, including experience in insurance, insurtech, or telematics. Relevant backgrounds may include product management, underwriting or risk solutions, commercial leadership, or strategic partnerships.
5–8 years of required leadership experience, including experience leading small teams or operating as a hands-on product leader who influences without direct authority, as well as 3+ 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).
A track record of leading customer-facing products, programs, or partnerships from discovery through delivery, with measurable customer or commercial outcomes.
Experience leading teams or influencing cross-functional groups, including the ability to operate hands-on and build momentum in a lean or developing domain.
Strong understanding of the insurance landscape, including usage-based insurance, underwriting, risk scoring, telematics data sharing, and relevant privacy and regulatory considerations. Experience working with insurers, carriers, or insurance partners is an asset.
Demonstrated track record in defining and tracking product KPIs, customer adoption metrics, investment portfolio stewardship, and negotiating strategic partnerships with commercial terms and technical integrations.
Strong cross-functional leadership, change readiness, and AI nativity to redesign domain workflows around AI and foster team development, collaboration, and high-trust organizational culture.
Flex working arrangements
Baby bonus & parental leave top up program
Online learning and networking opportunities
Electric vehicle purchase incentive program
Competitive medical and dental benefits
Retirement savings program
*The above are offered to full-time permanent employees only
The annual base salary for this position is the expected annual salary for this role, and may be subject to change. Geotab offers various perks and benefits and other compensation components that an individual may be eligible for. The actual base salary for this position depends on a variety of factors such as but not limited to skills, qualifications, education and overall experience, including the location the applicant lives while performing the job. This also includes equity with other team members and alignment with local market data. All offers of employment are contingent upon proof of eligibility to work and the individual's ability to pass a background check.