From driver training and telematics to claims management and E&S solutions, industry experts share their picks for a winning risk-management strategy.
By the Florida Surplus Lines Association (FSLA) with contributing authors Alyxandra Wagner, Vice President at RT Specialty, and Erin O’Leary of Shelly, Middlebrooks & O’Leary Inc.
Date: Sept. 16, 2026
National Truck Driver Appreciation Week is the perfect time to celebrate the heroes of the highway who keep our economy moving.
In recent years, Florida has passed meaningful legislation to address lawsuit and towing abuse, and the Florida Supreme Court ruled summary judgement may be made based on recorded video evidence. However, the trucking industry continues to face economic pressures from increased operating costs like fuel prices and rising insurance premiums.
“Nuclear verdicts are one of the most significant challenges facing the trucking industry,” said Alyxandra Wagner, Vice President at RT Specialty. “The impact of these large jury awards is being felt across the insurance marketplace, particularly with respect to truck brokerage liability and excess liability coverage. As a result, carriers are increasing premiums, requiring more detailed underwriting submissions, closely evaluating risk management protocols, and scrutinizing contractual relationships.”
The Florida Surplus Lines Association asked industry experts to lock in their fantasy picks for the team destined for a championship run.
The Driver is the MVP
During Truck Driver Appreciation Week, we recognize that the safest fleets are those that invest heavily in the well-being and professional growth of their drivers. Elite fleets know that a first-tier safety culture is the best offensive game plan on the board. By leveraging real-time telematics data, this team drafts an unbeatable strategy incentivizing drivers who hit high level safety metrics to eliminate turnovers and blindside operational hits.
“Fleet safety, driver hiring practices, training programs, regulatory compliance, and telematics continue to be major underwriting considerations for trucking risks,” said Wagner. “These factors can significantly influence a carrier’s willingness to consider an account and the terms they are willing to offer. Strong controls in these areas can help differentiate an account and often lead to more favorable underwriting outcomes, whereas deficiencies can result in reduced capacity, higher premiums, or declinations.”
The Championship Playbook: Winning with Technology
- Reaching the Super Bowl of trucking risk requires moving away from reactive management. Elite fleets dominate the field with a fully integrated tech stack.
- AI-Powered Dashcams: AI-powered cameras look outward and inward to identify distracted driving, tailgating, and fatigue before an incident occurs. The league’s best, use this data to run standard compliance drills with their drivers providing immediate constructive feedback and rewarding top-tier safety scores.
- Predictive Maintenance Sensors: A breakdown on the highway is a safety hazard and lost revenue.
- Integrated TMS and ELD: Seamless communication between Transportation Management Systems (TMS) and Electronic Logging Devices (ELD) ensures drivers are never pressured to violate Hours of Service (HOS) regulations to make a delivery. This ensures the fleet maintains flawless regulatory compliance on the highway.
- Advanced Driver Assistance Systems (ADAS): In-cab collision mitigation and lane alerts protect drivers during long-haul runs.
Rookie Threats
- Motus: The FMCSA recently launched a new management system. This is a crucial time for fleets to log in to the FMCSA portal and review their carrier details and insurance filing information to verify that all data is converted correctly.
- Housekeeping: Fleets should ensure all drivers and units operating under the insured’s authority have been properly reported to the insurance company.
- Driver qualification enforcement: Federal and state regulators are placing greater scrutiny on CDL qualifications and English language proficiency requirements.
The Injury Report
Market capacity is tightening especially on distressed risks, truck brokerage liability and excess liability risks.
One significant legal development for the trucking and freight industry this year is the U.S. Supreme Court’s unanimous decision in Montgomery v. Caribe Transport II, LLC, which ruled federal law does not shield freight brokers from state-level negligent hiring lawsuits. This opened a gap for broker lawsuits to pursue claims that had been previously blocked. In July 2026 a Dallas jury delivered a $604 million verdict against motor carrier Lupus Superior and freight broker C.H. Robinson over a fatal 2021 multi vehicle crash in Mississippi. The jury found the broker liable for negligent hiring and determined the truck driver acted as a “borrowed employee” under the broker’s control, expanding liability exposure.
The Waiver Wire
When traditional coverage sits on the bench, the Excess & Surplus (E&S) Lines market steps up. Wagner highlights, “One of the greatest strengths of the E&S marketplace is its flexibility and willingness to develop customized solutions for challenging risks. The E&S market often provides options when traditional markets are unable or unwilling to do so. These solutions can range from quota-sharing arrangements among multiple carriers to more sophisticated alternatives such as captives, structured risk programs, and layered insurance placements. The trucking industry continues to evolve, and the E&S marketplace evolves with it by developing creative solutions to address emerging exposures and changing market conditions.”
The Toughest Division: Claims
Even the best managed fleets will experience accidents. A strong offense helps drastically reduce their severity and frequency. Prompt claims reporting is essential. Accidents should be reported to the insurance company immediately, regardless of who appears to be at fault. Early reporting allows insurers and claims professionals to preserve evidence, investigate the circumstances, coordinate appropriate resources, and begin managing the claim before complications arise.
Cargo security is another critical component of claims prevention. High-value cargo requires consistent monitoring and strong security protocols to reduce the risk of theft.
The Final Score
In the insurance and logistics world, lifting the trophy means lower premiums, higher driver retention, and, most importantly, ensuring every single driver returns home safely at the end of their shift. By aggressively implementing cutting-edge technology, this fantasy pick is well on its way to an undefeated season in safety.
Published by the Florida Surplus Lines Association (FSLA) with contributing authors Alyxandra Wagner, Vice President at RT Specialty, and Erin O’Leary of Shelly, Middlebrooks & O’Leary Inc.
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