Staff Accountant
High Definition Vehicle Insurance
Accounting & Finance
Chicago, IL, USA
Posted on Aug 30, 2025
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
As our Staff Accountant, you will report to the VP of Finance as the first hire solely dedicated to overseeing the general accounting functions at HDVI. Your primary responsibilities will be performing and managing day-to-day transactional input and oversight, AR & AP processes, period-end closings, and ensuring compliance with generally accepted accounting procedures. As a key member of a growing finance team, you will be asked to create and implement new accounting processes and procedures, reconciliations, controls, automation, and much more. HDVI is a remote-work environment, providing opportunities to work from one of our offices as well as from home - ideally, this role will be based in the Chicago, Austin, Columbus or Greenville, SC metro areas.
What You'll Do
- Responsible for the end-to-end Accounts Receivable process including day to day billing responsibilities, receipt processing, and agent questions
- Oversight of the Accounts Payable processes for the company
- Prepare monthly premium reconciliation and initiate accurate and timely refunds
- Prepare the monthly supporting work paper files
- Assist with transition of finance to process automation
- Prepare or review bank reconciliations and run reports and complete other activities required to assure a complete and accurate month-end close
- Ensure all required journal entries are completed for all companies in accordance with GAAP. Maintain work papers to ensure all accounts are reconciled
- Assist with cash management and disbursements
- Work with the outside accountants on the year-end review audit, tax issues and other issues as needed
What You Have
- Bachelor's degree in Accounting or Finance
- Minimum 1-3 years accounting experience in the insurance industry.
- Strong knowledge of GAAP and STAT accounting principles
- Experience working for a full stack insurance organization
- Strong PC skills, including advanced Excel; proficiency in Outlook, Word
- Strong analytical and problem-solving skills
- Ability to communicate effectively with senior management and organize and present accounting data, budgets and variances to various audiences
- Thrive in a fast-paced work environment and adapt to a changing work environment
Benefits
- 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
