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Small fleet health benefits
1 to 25 employeesDrivers in many statesICHRA
Small fleets

Benefits that keep good drivers in your trucks

A small carrier competes with the big fleets for every good driver. The right health benefit does not have to be the most expensive one. It has to work where your drivers live and run.

Small group, level-funded and ICHRA compared for fleets with 1 to 25 W-2 employees
ICHRA lets each driver buy a plan in their own home state with your tax-free allowance
Clear rules on what you can and cannot offer leased owner-operators
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By Erik Moran, licensed health insurance broker (NPN 20970092) · Updated October 14, 2026

Three ways to cover W-2 drivers and staff

Quick answer

With at least one W-2 employee who is not an owner or an owner's spouse, a small trucking company can offer a traditional small group plan, a level-funded plan, or an individual coverage HRA (ICHRA). If your drivers live in several states, an ICHRA is often the cleanest fit, because each driver buys an individual plan in their own state and you reimburse premiums tax-free up to an allowance you set.

Small groupLevel-fundedICHRA
How it worksOne plan from one carrier for everyoneGroup plan with fixed monthly cost, built-in stop-loss, possible refund in a good yearYou set a monthly allowance; employees buy their own individual plans
Drivers in many statesNetwork must reach where each driver livesSameEach driver shops in their own state
Cost controlRenewal set by the carrierGood for healthy groupsYou fix the budget per employee class
Participation rulesCarriers usually require a share of eligible employees to enrollSimilarNo minimum participation

We work with businesses of 1 to 25 employees, and fleets that size are the sweet spot for all three. More detail in our guides to ICHRA and level-funded plans.

What you can do for leased owner-operators

Owner-operators leased to you are independent contractors, not employees, so they generally cannot be put on your employee group plan or your ICHRA. Treating them like employees for benefits can also muddy their contractor status. What you can do:

  • Keep the occupational accident program most leases require, which covers on-the-job injuries.
  • Point them to a broker who handles individual coverage for drivers. Our truck driver guide is written for them.
  • Keep it at that. Do not take payment for referrals unless your attorney has confirmed it is legal in your state.

Why ICHRA fits a fleet spread across states

A traditional group plan is built on one carrier's network in your home state. If your drivers live in Georgia, Alabama and Tennessee, some of them may end up with a network that is thin where their families actually see doctors. With an ICHRA:

  • Each employee picks a plan available in their own state and rating area.
  • You can set different allowances by class, such as full-time drivers, part-time staff or employees in different rating areas.
  • Reimbursements are tax-free to the employee and deductible to the company.
  • An employee offered an ICHRA that meets the affordability test cannot also take a Marketplace tax credit, which is part of the design.

What an ICHRA budget looks like

An ICHRA turns health benefits into a number you choose. Here is the arithmetic for an example fleet, before any taxes or plan prices:

W-2 drivers and staff8
Monthly allowance you set per employee$500
Most the company can spend in a month$4,000
Most the company can spend in a year$48,000, deductible as a business expense

Each employee buys an individual plan in their own state, and you reimburse actual premiums up to the allowance, so the true cost can come in under the maximum. The allowance figures here are an example, not a recommendation: we will help you set one that fits your budget, passes the affordability test you need, and compares fairly against a small group or level-funded quote.

Questions we hear most

Can a trucking company with one employee get group health insurance?

Generally yes, if that employee is a W-2 employee who is not an owner or an owner's spouse. A business of only owners and spouses does not qualify for small group coverage.

Can I put leased owner-operators on my company health plan?

Generally no. Independent contractors are not employees, so they are not eligible for employee group plans or an ICHRA.

Is ICHRA good for drivers who live in different states?

Often, yes. Each employee buys an individual plan in their own state and you reimburse premiums tax-free up to an allowance you set by employee class.

Price your fleet's options

Tell us how many W-2 employees you have and where they live. We will compare group, level-funded and ICHRA side by side.

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