Insurance Solutions for Transportation & Fleet Operations
From local delivery services to long-haul trucking, moving companies to school bus operators, Winter-Dent provides transportation insurance solutions that protect your vehicles, drivers, and business continuity. Whether you operate three vans or three hundred trucks, we build coverage that keeps you moving while managing the unique risks of the road.
Why Transportation Requires Specialized Coverage
Transportation businesses operate in a constantly moving environment: changing DOT regulations, driver shortages, accident liability, cargo responsibility, and the reality that your assets are exposed 24/7. Standard business insurance simply can’t address these mobile, high-velocity risks.
With the right coverage and proactive safety programs, you can keep your fleet rolling and your business profitable.
At Winter-Dent, we know fleet operations vary dramatically. Your vehicle types, routes, cargo, and driver profiles all shape your risk. We don’t start with price shopping – we start with understanding your operation.
Our Prevent365 process flips the traditional approach. Instead of reacting to accidents, we identify risk factors before they cause losses, strengthen driver safety programs, and build coverage designed for how your fleet actually operates.
Our Prevent365 process isn’t generic protection. It’s a strategic partnership to help you prevent, contain, and insure against risks that could sideline your fleet.
Every transportation business faces distinct exposures, from highway accidents to cargo claims. Winter-Dent builds protection around your specific operations, combining critical coverages that safeguard your drivers, vehicles, and revenue.
Provides coverage for bodily injury and property damage caused by your vehicles, meeting state minimums and customer contract requirements up to $1M or more.
Protects your vehicles against collision, comprehensive losses, theft, vandalism, and weather damage so you can repair or replace assets quickly.
Covers goods in transit against damage, theft, or loss while in your care, custody, or control, essential for protecting customer property and relationships.
Provides medical benefits and wage replacement for drivers and staff injured on the job, from loading accidents to vehicle-related injuries.
Protects against non-vehicle incidents like slip-and-falls at your facility, loading dock accidents, or injuries during deliveries.
Covers owner-operators when driving without a trailer or outside dispatch, filling the gap when primary liability doesn’t apply.
Protects trailers you’re hauling for others under interchange agreements, covering physical damage while in your possession.
Provides injury benefits for independent contractors and owner-operators who aren’t covered under traditional workers’ compensation.
Adds additional liability limits above your primary policies for catastrophic claims that exceed standard coverage.
Industry Expertise
Decades of experience across multiple industries, giving us deep insight into sector-specific risks and solutions.
Core Values
We prioritize long-term relationships over short-term sales, ensuring your success is our primary goal.
Risk Evaluation Process
Our proprietary Prevent365 methodology ensures comprehensive risk assessment before coverage placement.
Consultative Approach
We're your risk management partners, not just insurance brokers, providing ongoing support and strategic guidance.
Most transportation companies require commercial auto liability, physical damage coverage, motor truck cargo insurance, workers’ compensation, and general liability. Depending on your operation, you may also need non-trucking liability, trailer interchange, and excess liability. Winter-Dent customizes coverage for local delivery, long-haul trucking, moving companies, and specialized haulers.
Cargo insurance protects goods you’re transporting against loss, damage, or theft while in your care. Coverage limits typically range from $10,000 to $250,000+ depending on the value of goods you haul. Most shippers and brokers require proof of cargo coverage before contracting with carriers.
Absolutely. Even small fleets face significant liability exposure from accidents, cargo claims, and employee injuries. Many customers and contracts require minimum insurance levels. Winter-Dent helps small delivery operations, courier services, and local haulers secure affordable, compliant coverage.
Implement driver safety training, use telematics and dash cams, maintain strong hiring practices, perform regular vehicle maintenance, and document your safety culture. Winter-Dent helps transportation companies develop loss control programs that can significantly reduce premiums over time.
Primary liability covers your vehicles while under dispatch hauling loads. Non-trucking liability (bobtail coverage) covers owner-operators when not under dispatch – driving home, personal use, or deadheading. Both are essential for complete protection. Winter-Dent ensures no coverage gaps exist in your program.
Email Us
info@winter-dent.com
Call Us
(573) 634-2122