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.

In one sentence: Payroll Freedom provides payroll for roofing companies in Illinois and Wisconsin — including correct W-2 crew setup, pay-as-you-go workers’ comp, and electronic onboarding for storm-season hires — for a base fee of $45 to $95 per payroll run plus $3.35 to $9.70 per employee.

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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 contributions through payroll

Direct deposit & pay stubs

See how it works

Watch: How We Handle Roofing Payroll in Under 2 Minutes

In this video (1:34): electronic onboarding for storm-season hires, pay-as-you-go workers’ comp, W-2 payroll setup, retirement contributions through payroll, and payroll tax filings.

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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 may point to an employee relationship — whatever the paperwork says. A self-service payroll platform can process either classification without ever flagging the risk to you.

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Workers’ comp premiums hit hard at audit time

Roofing is typically among the higher-rated trades for workers’ comp. Annual audits based on estimated payroll mean either overpaying all year or facing a large true-up bill — and a misclassified crew can make that audit worse.

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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.

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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. If you’re moving your crew off 1099s, we help you make the switch smoothly. Pairs directly with worker classification review through our sister company, Accounting Freedom.

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Pay-As-You-Go Workers’ Comp

Premiums line up with your payroll cycle, so there are no lump-sum payments and no year-end audit surprises — especially valuable when premiums swing with payroll during storm season. Available as an add-on at $10 per payroll.

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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 Contributions Through Payroll

Contributions to your retirement plan run directly through payroll — SIMPLE IRA, 401(k), and other plans. 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.

Roofing is one of the trades we serve. See all contractor payroll services, or jump to Electrical, HVAC, Landscaping, or Plumbing.

What it costs

Transparent pricing, with every fee disclosed upfront.

Every payroll run has a base fee that depends on how often you pay: $45 weekly, $64 bi-weekly or semi-monthly, or $95 monthly. On top of that, you pay a per-employee rate: $3.35 on Core, $5.30 on Core+, or $9.70 on Core Pro.

Additional states are $10 per state per payroll, pay-as-you-go workers’ comp is $10 per payroll, and there’s a one-time $300 implementation fee. For example, a 10-person crew on a bi-weekly Core plan pays $97.50 per payroll.

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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