Director of Fleet Risk & Safety

Job Description

Job Description

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.

What You'll Do

• 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

What You Have

Preferred Skills

Benefits

We may use artificial intelligence (AI) tools to support parts of the hiring process, such as reviewing applications, analyzing resumes, or assessing responses. These tools assist our recruitment team but do not replace human judgment. Final hiring decisions are ultimately made by humans. If you would like more information about how your data is processed, please contact us.