Head of Insurance Solutions (Insurtech)

Location: Oakville, Ontario, Canada; flexible hybrid work model with office attendance expectations tailored to the role

Salary: $163,800–$227,500 CAD annual base salary

Company

hirify.global develops IoT, connected transportation, fleet management, web analytics, and machine learning solutions using vehicle data.

What you will do

• Own the product vision, strategy, roadmap, and outcomes for Insurance Solutions.
• Develop carrier partnership strategies and make build, buy, or partner decisions.
• Optimize the insurance journey for fleet operators, managers, and drivers while ensuring consent, privacy, and regulatory compliance.
• Build and scale product, design, and engineering capabilities while managing resources and investment priorities.
• Coordinate with platform, segment, solution, sales, marketing, and alliances teams to package solutions and align dependencies.
• Present strategy, investment cases, revenue contribution, and growth plans to executive and board leadership.

Requirements

• 10–12 years of overall experience, including 10+ years in product management, product engineering, or a related customer-facing product role.
• 5+ years in senior product leadership and 5–8 years of leadership experience involving teams or cross-functional influence.
• Deep knowledge of usage-based insurance, telematics data sharing, carrier ecosystems, underwriting, risk scoring, privacy, and regulatory requirements.
• Experience defining product KPIs, tracking adoption, managing investment portfolios, and negotiating strategic partnerships with commercial and technical terms.
• Bachelor’s degree in business, computer science, engineering, or a related field, or equivalent experience.
• Strong cross-functional leadership, change readiness, and ability to redesign workflows around AI.

Nice to have

• Experience with insurance, insurtech, or telematics partnerships.
• Experience leading small teams or operating as a hands-on product leader without direct authority.

Culture & Benefits

• Flexible hybrid work model combining in-person collaboration and virtual work.
• Home office reimbursement program.
• Parental leave top-up program and baby bonus.
• Medical and dental benefits and a retirement savings program for full-time permanent employees.
• Online learning and networking opportunities and an electric vehicle purchase incentive.

Hiring process

• Employment offers are contingent on proof of eligibility to work and successful completion of a background check.
• Workplace location and on-site attendance expectations will be clarified during the hiring process.