Most trucking companies think about insurance only when the bill comes due or after an accident. But according to Jessica Hollington of United Commercial Insurance, that way of thinking can cost carriers far more than money. "The biggest mistake people make is shopping insurance instead of shopping for the right insurance agent," Hollington said during a recent interview with FreightWaves. "The right agent can get you the right insurance if they truly care."
The Case for a Dedicated Agent
For Hollington, trucking insurance has always been personal. She grew up in a trucking family and remembers watching relatives struggle to get answers from insurance agents who never answered the phone or returned emails. One moment changed her career forever. Her cousin was supposed to attend his son’s first basketball game and a surprise birthday party. Instead, he was stuck at a customer because he couldn’t get a Certificate of Insurance after business hours. "I remember being that kid because my dad was a trucker," Hollington said. "My birthday never fell on the day I was born. It fell whenever my dad could be there."
Today, Hollington works only with commercial trucking insurance. She believes trucking companies deserve agents who understand the business instead of simply selling policies. "I’m not a transactional person," she said. "Your insurance agent should be there for you. We work for our customers." That relationship goes far beyond finding the cheapest premium. According to Hollington, one of the first people a trucking company should interview when starting or growing a business is its insurance agent. "If your insurance agent isn’t asking you questions, that’s a red flag," she said.
Questions Every Agent Should Ask
Hollington emphasized that a good agent will probe deeply into a carrier's operations. The questions an agent should ask include:
| Area of inquiry | Specific details to cover |
|---|---|
| Commodities | What exactly are you hauling? Not just "general freight" |
| Operating territory | Where do you operate? |
| Driver hiring | How do you hire drivers? |
| Safety policies | What safety policies are in place? |
| Growth plans | What does future growth look like? |
The Danger of Vague Cargo Descriptions
One of the biggest mistakes Hollington sees is carriers telling their insurance company they haul "general freight." "General freight is almost like a cuss word to me," Hollington joked. "What are you really hauling?" She explained that insurance companies need specific information because different cargo creates different risks. "If you haul one car during the year, you’re a car hauler," she said. "Cars are not general freight." Leaving out those details can create major problems when a claim is filed. Both Hollington and the FreightWaves reporter agreed that honest communication between carriers and their insurance agents is critical. "It’s always better that your insurance agent hears it from you first," Hollington said. "Better that it comes from you than the underwriter asking questions later."
Growth, Safety, and Documentation
Growth was another topic covered. Many owner-operators start with one truck before quickly adding more equipment and drivers. While growth is exciting, Hollington said safety programs have to grow with the business. "I really like working with the companies that are growing from one truck to three or five trucks," she said. "That’s when you need safety policies, hiring procedures and systems in place." She said insurance companies pay close attention to rapid growth because it often creates new risks.
Documentation also plays a major role in protecting trucking companies. Hollington didn’t hesitate when asked what every carrier should invest in: "Cameras, cameras, cameras," she said. "The camera is always right." She encouraged drivers to take pictures after accidents, write down what happened while the memory is fresh, and report claims quickly. "The first memory is your freshest memory," she said. "Get it documented."
The conversation also turned to workers’ compensation and occupational accident insurance. Many owner-operators believe that paying drivers as independent contractors reduces their liability, but Hollington noted that misclassification can lead to uncovered claims. A proper agent helps navigate these nuances.
Implications for Finance Executives
For CFOs and treasury directors, the advice from Hollington underscores that insurance is not a commodity purchase but a strategic risk-management decision. Selecting the wrong agent—or simply buying the cheapest policy—can leave a trucking company exposed to uncovered claims, regulatory penalties, and business interruption. Investing time in vetting an agent who understands the specific cargo, operations, and growth trajectory can reduce the total cost of risk over the long term.
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