Director of People Operations

Chicago, IL /
High Definition Vehicle Insurance – Operations /
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
We are looking for a Director of People Operations to join our team during an exciting time of growth and expansion at HDVI. In this position, you will drive our culture initiatives and design the systems and processes needed to grow & scale our teams. You have a background with high-growth tech startups and will prioritize delivering an exceptional employee experience. Ideally, you will have experience with talent acquisition, leadership & development, total compensation, and culture. You will report to the Head of Finance and will be hands-on with your direct reports. As our first people leader, you will work closely with all members of the executive team to understand our values and key metrics in order to create engaging people programs for our teams across 4 office locations and growing. HDVI’s success starts with people, making your job critical to the success of our company.

What You'll Do

    • Collaborate with senior leadership to understand the organization's goals and strategy related to staffing, recruiting, retention, and company culture
    • Plan, lead, develop, coordinate, and implement policies, processes, training, and initiatives to support HDVI’s vision and culture
    • Implement best in class recruiting strategies, processes, and tactics to attract the best talent
    • Lead the new hire orientation process and monitor their assimilation and early performance as a measure of recruiting success
    • Lead the internal performance management program and implement the structure, technology, and training necessary to continually enhance the review process and ensure effectiveness
    • Manage and maintain the relationship with our PEO in the near term, while charting the path to bring Human Resources in-house over time
    • Work closely with leadership to develop training and ongoing learning programs (created internally or by utilizing external vendors) specific to the needs of HDVI
    • Identify KPIs for the People Ops department to assess success and market competitiveness
    • Provide strategic direction and oversight on compensation and benefits to bolster our ability to attract and retain employees
    • Ensure compliance with federal and state employment laws and regulations
    • Drive content for all employee-related communications

What You Have

    • 7+ years of experience in People Operations roles
    • 3+ years of management experience
    • Experience with high-growth technology companies
    • SHRM Senior Certified Professional (SHRM-SCP) or SHRM Certified Professional (SHRM-CP) certification preferred
    • Experience recruiting and managing people, including teams across multiple regions, time zones, and regulations
    • Experience working with a variety of people systems: HRIS, ATS, compensation market data, engagement, and performance management systems
    • Exceptional written/verbal communication skills

If you are interested in this position, please contact the Recruiting Coordinator, Morgan Harrison. You can reach me at