Insurance
10 commercial auto insurance underwriting experts
These ten underwriters and underwriting leaders have underwritten commercial auto, fleet and trucking risks at insurance companies. A reader can learn how insurers underwrite commercial auto and fleet risks.
Professionals to explore
01—10Bailey Harr, CPCU
LinkedInExperience: Director of Fleet Underwriting · Canal Insurance Company
Former Director of Fleet Underwriting (2025–2026), Fleet Underwriting Manager (2023–2025) and Mid-Fleet Underwriting Supervisor (2021–2023) at Canal Insurance Company, and Assistant Vice President, Underwriting there since August 2026. The profile describes experience underwriting small and large fleets in commercial transportation insurance and managing an underwriting team.
Christopher Dougherty
LinkedInExperience: SVP Underwriting for Trucking · Lancer Insurance Company
SVP Underwriting for Trucking at Lancer Insurance Company since October 2024, and former Vice President there (2016–2024). The listing describes Lancer Insurance as offering commercial auto insurance. The profile also lists Managing Director at Janney Montgomery Scott LLC (2009–2015) and Fixed Income Trader at Merrill Lynch (2005–2009).
Craig Harmon
LinkedInExperience: Senior Fleet Underwriter · Nationwide
Former Senior Fleet Underwriter at Nationwide (2022–2023) and Comercial Truck Senior Underwriter, AINS, ARM at Great West Casualty Company (2011–2022). The profile also lists Underwriting Manager at Nirvana Insurance (2023–2026) and Sr. Transportation Underwriter at Berkley Small Business Solutions (a Berkley Company) since April 2026.
Dawn Hand
LinkedInExperience: Niche Underwriting Manager - Charter, Taxi, Intermodal, and Trucking · Coaction Global
Former Niche Underwriting Manager - Charter, Taxi, Intermodal, and Trucking at Coaction Global (2015–2021) and Senior Transportation Underwriter at Maxum Specialty Insurance Group (2006–2015), and Senior Fleet Underwriter at High Definition Vehicle Insurance (HDVI) since July 2024. The profile cites developing book strategies and guidelines and technical underwriting requirements.
Demetrius Johnson, MBA, CPCU, ARe
LinkedInExperience: Director of Fleet Underwriting · Canal Insurance Company
Former Director of Fleet Underwriting at Canal Insurance Company (2018–2020) and Director of Fleet Underwriting & Product Specialist Group at Progressive Insurance (2020–2022). The work history lists Vice President of Underwriting- CL Auto at The Hanover Insurance Group from June 2024, and a highlight describes a current role at Chubb leading the Commercial Auto line of business, with responsibility for underwriting strategy.
Don Williams
LinkedInExperience: National Line Lead Commercial Automobile Corporate Risk · Aviva Global Corporate & Specialty
National Line Lead Commercial Automobile Corporate Risk at Aviva Global Corporate & Specialty since September 2019, and also Senior Manager, Transportation Fleets, Complex Risk at Aviva Canada since April 2013. The profile also lists Director, Underwriting at Northbridge Financial Corporation (2000–2013) and says most of the person's career has been dedicated to serving the Canadian trucking industry.
Keith Cottingham
LinkedInExperience: Commercial Fleet Auto Underwriter · State Farm
Commercial Fleet Auto Underwriter at State Farm since November 2013. The profile says the person works with agency partners and field staff to assess new and re-underwrite existing business risk exposures, and combines judgment with underwriting guidelines to rate and bind desirable risks.
Kenny Asaro
LinkedInExperience: AVP Underwriting - Truck Transportation · RLI Insurance Company
AVP Underwriting - Truck Transportation at RLI Insurance Company since April 2022, and former Director of Underwriting - Truck Transportation (2017–2022) and Underwriting Manager - Truck Transportation (2016–2017) there. The profile also lists Underwriter - Starr Transportation at Starr (2015–2016) and Asst. Product Manager - Truck Alternative Products at National Interstate Insurance Company (2008–2015).
Neal Borzea, CPCU, AMIM, ARM, AU-M
LinkedInExperience: Underwriting Director · IAT Insurance Group
Underwriting Director at IAT Insurance Group since July 2025; the profile entry for this role reads "Truck insurance underwriter". It also lists Senior Transportation Underwriter at Great West Casualty Company (2007–2020), Lead Transportation Program Underwriter at Platinum Specialty Underwriters (2020–2024) and President - Underwriting at Ascension Specialty Insurance Group (2024–2025).
Robin Leblanc, CIP
LinkedInExperience: Senior Fleet Underwriter · Old Republic Insurance Company of Canada
Former Senior Fleet Underwriter (2015–2022) and Underwriting Supervisor (2022–2024) at Old Republic Insurance Company of Canada, and Underwriting Manager there since March 2024. The profile also lists Senior Commercial Automobile Underwriter at Economical Insurance (2007–2015) and Commercial Auto Underwriter at Kingsway General Insurance Company (2002–2007), and describes experience underwriting individual, fleet and garage risks.
Choose the right perspective
Match the fleet size and vehicle type to your question, since small fleets, large trucking fleets and specialty vehicles are underwritten differently. Also consider whether you need a hands-on underwriter's view of individual accounts or a manager's view of portfolio guidelines and results.
Questions to take into the conversation
- 01Which driver, vehicle and loss history factors weigh most when you decide whether to write a fleet account?
- 02How do you use telematics and safety program data in underwriting decisions?
- 03How did you respond when a commercial auto book's loss ratio started to deteriorate?
Reaching commercial auto insurance underwriting experts
How can I contact one of these commercial auto insurance underwriting experts?
Pick one of the 10 people on this page and choose "Book a paid call", or describe your project to find others. You offer a fee for a 15-minute call or a written answer, Instant Expert finds the person's work email and sends the invitation, and they decide whether to accept. The list covers 9 companies, including Canal Insurance Company, Lancer Insurance Company and Nationwide, based on profile data retrieved on October 4, 2026. Being listed here doesn't mean someone has agreed to take calls.
How much does it cost to reach commercial auto insurance underwriting experts?
You choose the offer, starting at $5 per person. It includes Instant Expert's 20% fee, so an offer that pays the person $100 costs you $125. You're charged only when the person books the call or sends the answer.
What if they don't reply?
You pay nothing. Instant Expert sends follow-up reminders, and if the person hasn't booked or answered within 7 days, the request expires and any hold on your card is released. You can invite several of the 10 people on this list at once and cap your total spend, so you pay only for the ones who accept.
About this directory
This is a professional research starting point based on business profile data retrieved on . Titles and companies reflect that source snapshot and may describe past or present roles. Check the linked profiles for current details. Inclusion does not imply Instant Expert membership or availability.
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