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Added 10 mins ago
WU
Senior Director, Strategy & Operations
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- Full-time
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Geotab

Head of Insurance Solutions

Toronto, ON, Canada

Hiring Range: $163,800 CAD - $227,500 CAD · Full-time

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Job details

Pay: Hiring Range: $163,800 CAD - $227,500 CAD
Job type: Full-time
Apply by: May 1, 2027
Experience: 10–12 years of relevant experience, including experience in insurance, insurtech, or telematics.
Posting language: English
Posted: Nov 2, 2026

Original job description

Who we are:Geotab ® is a global leader in IoT and connected transportation and certified “Great Place to Work™.” We are a company of diverse and talented individuals who work together to help businesses grow and succeed, and increase the safety and sustainability of our communities. Geotab is advancing security, connecting commercial vehicles to the internet and providing web-based analytics to help customers better manage their fleets. Geotab’s open platform and Geotab Marketplace ®, offering hundreds of third-party solution options, allows both small and large businesses to automate operations by integrating vehicle data with their other data assets. Processing billions of data points a day, Geotab leverages data analytics and machine learning to improve productivity, optimize fleets through the reduction of fuel consumption, enhance driver safety and achieve strong compliance to regulatory changes. Our team is growing and we’re looking for people who follow their passion, think differently and want to make an impact. Ours is a fast paced, ever changing environment. Geotabbers accept that challenge and are willing to take on new tasks and activities - ones that may not always be described in the initial job description. Join us for a fulfilling career with opportunities to innovate, great benefits, and our fun and inclusive work culture. Reach your full potential with Geotab. To see what it’s like to be a Geotabber, check out our blog and follow us @InsideGeotab on Instagram. Who you are:

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!

What you'll do:

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.

How you'll make an impact:

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.

What you'll bring to this role:

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.

If you got this far, we hope you're feeling excited about this role! Even if you don't feel you meet every single requirement, we still encourage you to apply. Please note: Geotab does not accept agency resumes and is not responsible for any fees related to unsolicited resumes. Please do not forward resumes to Geotab employees. This posting is for an existing vacancy. Why job seekers choose Geotab:

Flex working arrangements Home office reimbursement program 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

How we work:At Geotab, we thrive on a flexible hybrid work model that combines the dynamic energy and connection of in-person collaboration with the independence and flexibility of virtual work. We believe that coming together in person is fundamental to cultivating trust, nurturing a vibrant culture of belonging, and fostering meaningful innovation across our diverse teams. Office visit schedules are tailored thoughtfully based on role requirements. Specific expectations regarding workplace location and on-site attendance for this position will be shared during the hiring process. We believe that ensuring diversity is fundamental to our future growth and progress and is an integral part of our business. We believe that success happens where new ideas can flourish – in an environment that is rich in diversity and a place where people from various backgrounds can work together. Geotab encourages applications from all qualified individuals. We are committed to accommodating people with disabilities during the recruitment and assessment processes and when people are hired. We will ensure the accessibility needs of employees with disabilities are taken into account as part of performance management, career development, training and redeployment processes. If you require accommodation at any stage of the application process or want more information about our diversity and inclusion as well as accommodation policies and practices, please contact us at careers@geotab.com. By submitting a job application to Geotab Inc. or its affiliates and subsidiaries (collectively, “Geotab”), you acknowledge Geotab’s collection, use and disclosure of your personal data in accordance with our Privacy Policy. Click here to read our Privacy Notice.

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.

Hiring Range: $163,800 CAD - $227,500 CAD

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More about this job

Responsibilities

Own the Insurance Solutions product vision, roadmap, carrier partnerships, and customer outcomes, with a focus on measurable fleet savings, adoption, retention, and revenue growth. Lead and develop the team, manage investments and business performance, and coordinate with platform, segment, sales, marketing, and executive stakeholders.

Requirements

Requires 10–12 years of relevant experience, including insurance, insurtech, or telematics experience, and 5–8 years of leadership experience. Candidates should have a bachelor's degree or equivalent experience, a record of delivering customer-facing products or partnerships, and strong expertise in insurance, product KPIs, commercial partnerships, and cross-functional leadership.

Skills

Product Strategy
Product Roadmapping
Insurance Solutions
Insurance Partnerships
Telematics
Usage-Based Insurance
Underwriting
Risk Scoring
Customer Experience
People Leadership
Cross-Functional Leadership
Commercial Strategy
P&L Management
Investment Prioritization
Privacy and Regulatory Compliance
AI-Enabled Workflow Design

Benefits

Flexible Work Arrangements
Home Office Reimbursement
Baby Bonus
Parental Leave Top-Up
Online Learning Opportunities
Networking Opportunities
Electric Vehicle Purchase Incentive
Medical Benefits
Dental Benefits
Retirement Savings Program

Visa sponsorship

Not detected in the job text

Keywords

Insurance Solutions
Insurtech
Telematics
Connected Transportation
Internet of Things
Fleet Data
Usage-Based Insurance
Underwriting
Risk Scoring
Data Sharing
Privacy
Regulatory Compliance
Product Strategy
Product Roadmap
Carrier Partnerships
Strategic Alliances
Customer Experience
Product KPIs
Program Adoption
Customer Retention
Monthly Recurring Revenue
Investment Portfolio
Build-Buy-Partner Decisions
Cross-Functional Coordination
AI-Enabled Workflows
Fleet Management
Data Analytics
Machine Learning
Geotab Marketplace

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