Roofing and construction work is physical, seasonal, and short on people willing to do it well. If you run crews, you already know the real competition is not just other bids, it is other employers trying to hire the same framers, roofers, and laborers you rely on. A real group health plan is one of the clearest ways a small contractor can stand out, and it is more affordable and easier to set up than most owners expect.
Contractor crews are a tough fit for off the shelf insurance shopping. Headcounts move up and down with the season, jobs and job sites change constantly, and most owners are juggling a mix of long term W-2 employees and 1099 subcontractors on the same project. National insurance sites are not built to sort through that, so a lot of roofing and construction owners either overpay for a generic plan or give up on offering coverage at all. A broker who understands how crews are actually staffed can build a plan around your real payroll instead of a template.
This is the single most common point of confusion we run into with contractors, so it is worth being direct about it: workers' compensation and group health insurance are not the same coverage, and one does not replace the other.
A crew member who breaks an arm on a roof needs workers' comp. That same crew member's kid with strep throat, or their own annual physical, needs health insurance. Most contractors ultimately need both, and having a real health plan on top of required workers' comp is exactly what separates a contractor who is easy to work for from one that is not.
Most roofing and construction businesses run a blend of payroll employees and subcontracted labor, and that mix affects how a group plan gets built:
Bottom line: you do not have to cover every person on a job site to offer real benefits. A plan built around your core W-2 crew, with individual options available for subcontractors, covers the people you most want to retain without overcomplicating payroll.
Costs vary based on your state, the carrier, your crew's ages, and how the plan is structured, so there is no single number that applies to every contractor. Small group plans are generally available to businesses with as few as 2 enrolled employees, and many owners choose to contribute a fixed percentage or dollar amount per employee rather than covering the full premium, which keeps the cost predictable while still giving your crew real coverage. The only way to know your actual number is to get a quote run against your specific headcount.
Based in Fort Lauderdale, we work with roofing companies and construction contractors across South Florida and beyond. Florida's year-round building season means crews rarely go through the long seasonal layoffs contractors in colder states deal with, which makes it easier to structure stable, ongoing group coverage instead of constantly re-enrolling a rotating crew.
Yes. Small group health plans are available to businesses with as few as 2 enrolled employees. Crew size, not company size, is usually what carriers look at, so a small roofing outfit or construction crew can qualify the same as a larger contractor.
No. Workers' compensation and group health insurance are separate and both matter. Workers' comp covers job related injuries and is typically required by state law. Group health insurance covers everyday medical care, illness, prescriptions, and non job related injuries for your crew and their families. Most contractors need both.
Yes. Group health plans are generally built around W-2 payroll employees. 1099 subcontractors are independent businesses and typically shop their own individual coverage, which we can also help them compare, but they are usually not eligible for your company group plan.
It varies by state, carrier, crew age, and plan design, but small group plans commonly run a few hundred dollars per employee per month before any employer contribution strategy is applied. A broker can run exact numbers for your specific crew at no cost.
Tell us your headcount and how your crew is structured, W-2, 1099, or both, and we will map out real options for free.
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