Director of Fleet Services
What we do
High Definition Vehicle Insurance (HDVI): Technology meets Insurance. HDVI brings telematics, software and data together with commercial trucking insurance, taking transportation insurance and fleet risk management to the next level. Our platform arms fleets with an end-to-end solution that empowers them to save money, mitigate risk, and increase operational efficiencies. Our customers are small to midsize truck fleet operators who benefit from dynamic and transparent pricing – automatically reducing their premiums for safer driving. Leveraging a best-in-class partner ecosystem, HDVI combines magnitude and stability with innovation to revolutionize the commercial trucking insurance space.
Why work here
HDVI is building the industry defining commercial auto insurance company for the next 100 years. The $50 billion commercial auto industry hasn’t seen real innovation for decades and is broken in a number of ways, creating a significant opportunity for HDVI. HDVI is co-founded by a former Esurance co-founder, and has a senior management team with experience building innovative insurance and logistics companies from zero to $1B+ enterprises, and deep expertise in trucking insurance. HDVI is well-funded by leading logistics and mobility-focused venture capital firms and strategic investors including Munich Re, Daimler Trucks and Qualcomm. The HDVI Team is values-driven, data-driven, ambitious, and collaboratively minded with a diverse background of experiences and skills in the insurance and logistics industries. We like challenges and building solutions that improve the quality of life for our customers. We offer generous benefits, including employee stock options, health, dental, vision, 401k, flexible work environment, and unlimited PTO.
About the Role
The Director of Fleet Services will oversee the strategic and operational leadership of HDVI’s Fleet Services team. This position is responsible for managing the pre-bind fleet safety inspection process with prospective insureds, driving customer engagement with HDVI safety tools and services, and helping insured fleets improve safety and compliance outcomes. You will play a key role in developing proactive strategies to reduce risk, improve claim outcomes, and support premium growth through consultative and value-added services.
The ideal candidate has a strong background in trucking insurance loss control, fleet safety, transportation risk management, and fleet safety, coupled with experience leading teams and managing cross-functional initiatives in a fast-paced, tech-enabled environment.
- Lead the Fleet Services department, including Fleet Services Representatives, Operations Associates, and related support staff
- Develop and execute a department roadmap aligned with HDVI’s goals for loss control, customer retention, and growth
- Establish and monitor KPIs to track the effectiveness of safety engagement, onboarding efficiency, and customer outcomes
- Ensure strong collaboration between Fleet Services and Underwriting, Claims, Business Development, Product, and Engineering teams
- Guide the structure and content of fleet safety performance reviews and oversee the delivery of safety, compliance and coaching recommendations for HDVI insureds
- Oversee and optimize the pre-bind call process for large fleets to ensure risk evaluation provided to underwriting is consistent, efficient, and effective
- Ensure onboarding processes for new insureds (across all fleet sizes) are standardized, timely, and create a seamless customer experience
- Monitor fleet compliance with telematics and camera installation requirements and proactively escalate non-compliance issues
- Act as a voice of the customer and Fleet Services team with Product and Engineering to enhance existing tools and build new solutions
- Partner with Marketing and Sales to develop messaging, collateral, and success stories that highlight the value of HDVI’s Fleet Services
- Maintain alignment with Claims and Underwriting around crash notifications, FNOL, and support of claims-related video and telematics data requests
- Develop and maintain SOPs to support onboarding, pre-bind inspections, KPI calls, telematics compliance monitoring, and claim/crash handling
- Manage department budget, resource planning, inventory management, and vendor partnerships for dash camera/telematics products and services
- Bachelor’s degree in Business Administration, Transportation, Logistics, Risk Management, Safety, or a related field required
- 7+ years of progressive experience in fleet safety, loss control, transportation compliance, or risk management
- 3+ years in a leadership role managing teams, ideally in a commercial transportation, insurance, or SaaS environment
- Experience using or managing telematics solutions (Samsara, Motive, GeoTab, Netradyne, etc.)
- Familiarity with CSA scores, FMCSA regulations, Hours of Service rules, and driver coaching strategies
- Strong analytical skills with the ability to interpret data and generate actionable insights
- Excellent communication skills – both verbal and written – with executive presence
- Proficient in CRM platforms (e.g., Dynamics), Google Workspace, Microsoft Office, and telematics dashboards
- Skilled at project management, process improvement, and change management
- Passion for innovation, customer service, and improving road safety
- Advanced degree or relevant certifications (CDS, CRSP, CSP, ARM, etc.)
- Experience working in an insurtech, logistics tech, or commercial insurance startup
- Proven track record of using telematics data to inform safety or pricing decisions
- Understanding of insurance operations and loss ratio optimization
- Comfortable presenting to executive teams, board members, and enterprise customers
- Competitive salary & stock options - we want our success to be yours too
- Unlimited PTO with 11 paid holidays each year
- Medical, Dental, Vision, Short/Long Term Disability, Basic Life, and AD&D to support you and your well-being
- FSA / HSA programs
- 401(k) retirement plan with company match contribution
- Inclusive Parental Leave policy that supports all parents
- Wednesdays are standing meeting-free, allowing you to focus on deep work without distractions
- Birthday meal reimbursement, because celebrating our employees is part of our company culture
- A remote-friendly environment with the opportunity to participate in periodic in-person team offsites
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HDVI provides commercial fleets with an innovative insurance product that is revolutionizing how trucking insurance is rated today. With our dynamic approach and easy-to-use tools we are able to reduce insurance costs, increase safety and mitigate...
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