Insurance for Mid-Size Fleets in New York
Coverage strategies, pricing, and management tips for NY businesses with 10-50 commercial vehicles.
TL;DR: Mid-size fleets (10-50 vehicles) unlock volume discounts of 15-25%, experience rating, composite rating, and aggregate deductibles. Typical costs range from $1,800-$6,000/vehicle depending on mix. Key best practices: centralized records, annual MVR checks, telematics, and quarterly policy reviews.
Last updated: April 2026 · Written by the First Heritage Insurance Agency (FHIA) Commercial Insurance Team
What Makes Mid-Size Fleets Different
Businesses with 10-50 vehicles sit in a unique spot. You are too large for small-business commercial auto products but not big enough for the large fleet programs that Fortune 500 companies use. This means you need a broker who knows which carriers write aggressively in the mid-size fleet space and can structure your policy for maximum savings.
Mid-Size Fleet Pricing Advantages
With 10+ vehicles, you unlock pricing tiers that are not available to smaller operations:
- Volume discounts: 15-25% below individual vehicle pricing
- Experience rating: Your fleet's own claims history starts to outweigh industry averages in pricing
- Composite rating: All vehicles rated together instead of individually, smoothing out high-cost vehicles
- Aggregate deductibles: One annual deductible pool across the fleet instead of per-vehicle
- Dedicated claims handler: Some carriers assign a single adjuster to your fleet for consistency
Coverage Structure for Mid-Size Fleets
A mid-size fleet policy typically includes:
- $1M CSL liability (minimum; many carry $2M or more with umbrella)
- Physical damage on all vehicles (collision + comprehensive)
- Hired and non-owned auto
- Uninsured/underinsured motorist
- Medical payments coverage
- Motor truck cargo (if transporting goods)
Plus endorsements for your specific operations. See our endorsements guide.
Fleet Management Best Practices
- Centralize vehicle records. Maintain a master spreadsheet of all vehicles: VIN, year, make, model, assigned driver, garaging location, annual mileage.
- Run annual MVR checks. Check every driver's motor vehicle record at hiring and annually. Remove or exclude drivers with poor records. Driver requirements guide.
- Implement telematics. GPS tracking and dashcams reduce claims frequency by 20-30% and earn carrier discounts. Telematics savings guide.
- Establish a safety program. Regular driver safety meetings, defensive driving courses, and incident review processes demonstrate risk management to carriers.
- Review coverage quarterly. Vehicles are added and removed throughout the year. Make sure your policy reflects your current fleet. Adding vehicles | Removing vehicles.
Typical Costs for Mid-Size Fleets in NY
| Vehicle Mix | Per Vehicle/Year | 20-Vehicle Fleet Total |
|---|---|---|
| Service vans only | $1,800-$3,000 | $36,000-$60,000 |
| Mixed (vans + pickups) | $2,000-$3,500 | $40,000-$70,000 |
| Box trucks + vans | $2,500-$4,500 | $50,000-$90,000 |
| Heavy trucks (flatbed, dump) | $3,500-$6,000 | $70,000-$120,000 |
Not Sure If Your Business Qualifies?
Our commercial auto specialists can review your fleet, drivers, and operations to find the right coverage at the best rate. No obligation, no pressure.
Most businesses get a quote within 24 hours
What Our Clients Say
"I have had First Heritage for over 2 and a half years. They were recommended to me when I was purchasing my house and I cannot express enough how incredible they are. Friendly, responsive, and always looking out for my best interest."
Ashley L. - Google Review
"First Heritage saved our construction company over $12,000 on our fleet policy. They found carriers that actually understood our business instead of treating us like a number. Best decision we made for our commercial auto coverage."
Mike R. - Google Review
"We run 15 service vans on Long Island and First Heritage got us preferred tier pricing that our previous broker said was impossible. Their knowledge of the commercial auto market in New York is unmatched."
David K. - Google Review
"After getting non-renewed by our carrier, First Heritage placed our entire fleet within a week. Professional, responsive, and they actually understand the insurance needs of New York businesses. Cannot recommend them enough."
Jennifer M. - Google Review
Why Choose FHIA for Mid-Size Fleets
We are not a call center or a quoting platform. First Heritage is the managing general agency (MGA) behind FirstClass, our own commercial auto program. If your fleet qualifies, our in-house team makes the underwriting decision under authority delegated by the program’s insurers. If it isn’t a fit for the program, we place it with other carriers we represent. Either way, the same licensed team handles your account from first quote to bound policy.
FirstClass policies are issued by Pennsylvania Manufacturers’ Association Insurance Company (NAIC 12262), Manufacturers Alliance Insurance Company (NAIC 36897), or Pennsylvania Manufacturers Indemnity Company (NAIC 41424) — all members of the Old Republic Insurance Group, each with its principal office in Blue Bell, Pennsylvania. Your issuing company is identified before you bind. Accounts placed outside the FirstClass program are written by other insurance carriers we represent. First Heritage Insurance Agency Inc. is licensed as an insurance producer in New York (licence nos. BR504706 and PC504706).
Direct Access, No Hand-Offs
You work directly with the team that underwrites FirstClass accounts — and when a fleet isn’t a fit for the program, the same people place it with the carriers we represent.
Flexible, Common-Sense Underwriting
We look at the full picture of your business, not just a risk score. Real underwriting by real people.
Tailored for Mid-Size Fleets
Custom coverage solutions built specifically for your operation, not cookie-cutter packages.
Faster Turnaround
We control the process from start to finish. Most quotes delivered same day, COIs within 24 hours.