→ Fleet Resources → Driver Safety → One Incident Can End It All: What Small Fleets Must Do to Stay Insurable
Derek Legg is a Commercial Insurance Advisor at Levitt Group of Colorado, specializing in high-exposure industries including contractors, landscapers, electrical services, towing companies, and service fleets running 10 to 50 vehicles. His work focuses on helping operators manage risk, stay insurable, and avoid catastrophic loss. A former competitive sports coach, Derek brings a team-accountability lens to fleet risk conversations. He works alongside a dedicated risk management specialist, giving clients hands-on support that goes beyond policy placement.
Derek Legg is a Commercial Insurance Advisor at Levitt Group of Colorado. He works with contractor and service fleets on risk management, insurability, and the practical steps that keep small operators protected when the unexpected hits.
Small fleet operators are living in a risk environment that most of them do not fully understand. A contractor with 10 trucks is not managing a scaled-down version of an enterprise fleet program. They are running a business where a single accident, a single bad hire, or a single lapse in maintenance protocol can trigger a claim large enough to shut them down. Yet most of them are hiring without checking MVRs, skipping post-incident documentation, and relying on informal driver coaching that never gets past “be careful out there.”
Derek Legg advises commercial clients across these exact industries at Levitt Group of Colorado. He sees the same vulnerabilities repeated across accounts: young drivers placed behind company vehicles without a real vetting process, cell phone distraction that is talked about in casual conversation but never trained against, and maintenance issues that quietly stack up into carrier red flags. His approach draws from years of sports coaching and translates directly into how he talks to clients about team accountability and culture.
In this Roadrageous episode, Derek breaks down the specific exposures that small fleets overlook, explains why cameras and telematics are protection tools first and surveillance tools last, and lays out the three practical fixes every contractor fleet needs to make this year. The conversation is direct, operational, and built for the fleet owners who are making these decisions without a dedicated safety department behind them.
Hiring is hard. For contractors, it has become even harder. When a landscaping company or electrical contractor needs drivers, they often take who they can get, and who they can get is frequently younger, less experienced, and carrying a driving history that insurance carriers find uncomfortable.
Derek is direct: carriers get nervous around young drivers, and they have data to back it up. The owner sees a motivated 20-year-old who shows up and works hard. The carrier sees actuarial exposure. “They’re fired up to do their job,” Derek says. “But you still have to put that person behind a vehicle and drive for you.” The issue is not the worker. The issue is whether the fleet has a structured approach to onboarding that driver into safe behavior, or whether they just hand over keys and hope for the best.
Cell phone distraction is the first gap Derek identifies. Most drivers know they should not be on their phones. Few have ever sat through a training session that made the consequences feel real. When every employee is one pocket away from their screen all day, the habit carries directly into the cab.
Maintenance protocols are the second. Derek sees fleets where drivers notice vehicle issues but have no clear reporting system. Carriers track towing incidents and deferred maintenance as underwriting signals. A pattern of neglect raises premiums before a single major claim occurs.
Post-incident documentation is the third. Derek recommends a step sheet: a simple document in every vehicle that tells any driver exactly what to record and report in the 30 minutes after an incident. Without it, claims get muddied, fault disputes drag on, and settlements climb. “The more information we can provide throughout that process, the better,” he says.
Most contractors interview, offer the job, and only then check the driver’s Motor Vehicle Record. By that point, the candidate has mentally started the role, and sending someone away because of a colorful driving history creates friction the owner tries to avoid.
Derek pushes for a different sequence: make MVR review part of the conditional offer, not a post-hire formality. His team has encountered cases where a record check revealed a license already under suspension. “We actually have run into that before,” he says. Once the hire is made and something happens, the operator cannot demonstrate due diligence and the liability exposure grows significantly.
Resistance to dashcams is common in smaller fleets, usually centered on cost and privacy. Derek leads with the practical argument: one incident captured on camera can determine a claim outcome that would otherwise become a costly dispute. He is currently working a case where the other party is claiming fault and the camera footage will resolve it. Without footage, the commercial operator often loses by default.
The carrier incentive gap is real. Derek acknowledges that premium discounts for telematics adoption are not yet meaningful for small operators. But the math shifts entirely after one nuclear verdict, which are no longer limited to large, well-known companies.
Derek Legg is not talking to fleet managers at Fortune 500 companies. He is talking to the landscaping contractor with 12 trucks, the electrical service company with young drivers rotating in and out, and the towing operation that has never had a post-incident protocol because nothing bad has happened yet. His message: the absence of a major claim does not mean the risk is absent.
The steps he outlines do not require a dedicated safety department or a large budget. They require an operator willing to build a few simple systems and a broker who asks the right questions before a claim forces those conversations.
For small fleet operators looking to stay insurable in a tightening market, Derek’s experience offers a realistic and actionable starting point.
Derek Legg is a Commercial Insurance Advisor at Levitt Group of Colorado, where he focuses on high-exposure commercial accounts across the contractor, service fleet, and trades industries. His work centers on helping operators understand their actual risk profile, stay ahead of carrier requirements, and build the internal protocols that keep their businesses insurable.
Before joining Levitt Group, Derek came to the insurance industry through a family connection during a relocation from Oregon to Colorado. His background in sports coaching, particularly baseball, shapes how he approaches driver accountability, team culture, and the leadership conversations that actually change fleet behavior. He works alongside David Mobier, Levitt Group’s dedicated risk management specialist, to bring clients support that goes well beyond standard policy placement.
Derek’s approach is direct and client-first. He believes that small fleet operators deserve the same quality of risk guidance that larger companies take for granted, and that the right advisor can make the difference between a recoverable claim and a business-ending event.
This episode is brought to you by IMPROVLearning. At IMPROVLearning, we transform driver education through research-backed training methods. Our SPIDER Driver Training platform builds hazard recognition and decision-making skills that complement fleet technology investments.
For small and mid-size fleets without dedicated safety departments, SPIDER provides structured training that directly addresses the exposures Derek identifies: distracted driving, cell phone use, and in-cab decision-making under pressure. Technology catches what drivers do. Training changes what they decide to do.
Learn more at improvlearning.com.
Derek Legg is a Commercial Insurance Advisor at Levitt Group of Colorado, specializing in high-exposure industries including contractors, landscapers, electrical services, towing companies, and service fleets running 10 to 50 vehicles. His work focuses on helping operators manage risk, stay insurable, and avoid catastrophic loss. A former competitive sports coach, Derek brings a team-accountability lens […]
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