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Roofing Company Payroll IL & WI | Payroll Freedom

Payroll for Roofing Companies

Roofing payroll comes with real classification risk. We help you get it right.

High workers’ comp premiums, storm-driven crew surges, and the temptation to pay roofers as 1099s — roofing payroll carries more risk than most trades. We set crews up correctly on W-2, manage pay-as-you-go workers’ comp, and handle the rest. 20+ years serving small businesses.

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What we handle for roofing companies
Correct W-2 crew setup
Pay-as-you-go workers’ comp
Electronic new hire onboarding
Storm-season crew scaling
Payroll tax filings
Retirement plan administration
Direct deposit & pay stubs
The roofing payroll problem

Roofing payroll carries real risk that most providers don’t flag.

High workers’ comp premiums make 1099 classification tempting in roofing — and it’s also one of the most heavily scrutinized issues in construction. Here’s what generic payroll setups miss.

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Crews paid as 1099s create real audit exposure
If you set the schedule, supply materials, and direct the work, that’s an employee relationship — regardless of the paperwork. A self-service payroll platform will process either classification without ever flagging the risk to you.
🛡️
Workers’ comp premiums hit hard at audit time
Roofing carries some of the highest workers’ comp rates of any trade. Annual audits based on estimated payroll mean either overpaying all year or facing a large true-up bill — and a misclassified crew makes that audit even worse.
⛈️
Storm season creates sudden staffing surges
A major hailstorm can mean hiring five new crew members in a week. Generic payroll systems aren’t built for rapid onboarding at the exact moment you’re busiest and have the least time to spare.
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New hire paperwork slows down storm response
When the phone is ringing with storm damage calls, the last thing you need is paper I-9s and W-4s holding up a new crew member’s first day on a job site.
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No retirement plan means losing experienced crew leads
Your most experienced crew leads have options — especially in a tight skilled labor market. A retirement plan is a meaningful retention tool and a tax benefit for you as the owner.
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Your payroll company doesn’t know your name
You’ve got a classification or payroll question the morning after a storm. Your national provider has a hold queue. We have a person — in Mundelein or Grafton — and you know who they are.
How we solve it

Roofing payroll, set up correctly — and built for storm-season speed.

We bring the platform and the people to handle payroll the way a roofing business actually needs it done. On iSolved. With a real local team behind it.

⚠️
Correct W-2 Crew Setup
We help you set crews up correctly as W-2 employees from the start, so you’re not carrying classification risk that compounds with every payroll run. Pairs directly with worker classification review through our sister company, Accounting Freedom.
🛡️
Pay-As-You-Go Workers’ Comp
Premiums calculated on actual payroll each period and remitted automatically. No large upfront deposit. No year-end audit surprise — especially valuable given how much roofing workers’ comp rates can swing with crew size.
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Electronic Employee Onboarding
New crew members complete I-9s, W-4s, direct deposit authorizations, and state withholding on their phone — before day one. When storm season hits and you need crew fast, onboarding doesn’t slow you down.
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Storm-Season Crew Scaling
We help you scale crew up and down quickly during storm response without losing track of onboarding, classification, or tax filing requirements in the rush.
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Retirement Plan Administration
We administer SIMPLE IRA, 401(k), and other plans through iSolved — contributions flow directly from payroll. Helps you retain experienced crew leads who have offers from competitors.
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Payroll Tax Filing
We handle federal and state payroll tax deposits and filings. Learn more about Illinois payroll tax requirements and Wisconsin payroll tax requirements for small businesses.

Not sure if your current crew is classified correctly? Our sister company Accounting Freedom reviews worker classification against IRS guidelines as part of their roofing advisory work. One call, both sides covered.

Ready to get payroll right?

Your crew works hard in tough conditions. Their payroll shouldn’t add risk.

Let’s walk through your current crew setup and show you what correct classification, pay-as-you-go workers’ comp, and fast electronic onboarding could look like on iSolved — no commitment, no pressure.

Request a Meeting See Your Price

Illinois: 847-566-0902  |  Wisconsin: 262-375-2440

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