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Payroll for Landscaping Companies in IL & WI | Payroll Freedom

Payroll for Landscaping & Snow Removal

Landscaping payroll is seasonal, complex, and never slows down. We handle it so you can.

Seasonal hiring surges, variable crew sizes, timekeeping across job sites, and pay-as-you-go workers’ comp — landscaping payroll has more moving pieces than most industries. We’ve been handling it for 20+ years for businesses in Illinois and Wisconsin.

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What we handle for landscapers
Seasonal workforce onboarding & offboarding
Electronic I-9 and new hire paperwork
Timekeeping across multiple job sites
Pay-as-you-go workers’ comp
IL & WI payroll tax filings
Retirement plan administration
Direct deposit & pay stubs
The landscaping payroll problem

Generic payroll software wasn’t built for a seasonal crew.

Most payroll providers can handle a steady 9-to-5 staff. Landscaping payroll is a different animal — and when your provider gets it wrong, you feel it.

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Seasonal onboarding is a paperwork avalanche
Hiring 8–12 crew members in March and April — I-9 forms, W-4s, direct deposit setups, state withholding — takes hours your office doesn’t have right before your busiest season starts.
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Tracking time across multiple job sites is a daily headache
Without a proper timekeeping system, you’re collecting paper timesheets or relying on crew leads to text in hours. Errors pile up. Payroll takes longer than it should. Disputes happen.
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Workers’ comp premiums are unpredictable
Annual workers’ comp audits at the end of the season are stressful — and the true-up can be a surprise. Pay-as-you-go workers’ comp ties premiums directly to actual payroll, eliminating the audit scramble.
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No retirement plan means losing good people
Your full-time crew — foremen, account managers, equipment operators — are worth keeping. A retirement plan is one of the most effective retention tools available. Most landscapers don’t have one.
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Your payroll company doesn’t pick up the phone
You’ve got a paycheck question at 8 AM on a Monday before crews go out. Your national provider has a hold queue and a ticket system. We have a person — and you know their name.
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Snow season creates a completely different payroll pattern
Your winter crew may overlap with your summer staff — or be entirely different. Managing two seasonal payroll cycles with different hours, different pay rates, and different tax implications in the same calendar year needs a system, not a spreadsheet.
How we solve it

Landscaping payroll handled right — every crew, every season, every year.

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

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Electronic Employee Onboarding
New hires complete I-9s, W-4s, direct deposit forms, and state withholding on their phone or tablet — before their first day. Your office doesn’t touch paper. Onboarding a spring crew of 12 takes hours, not days.
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Timekeeping for Field Crews
iSolved Time lets crew members clock in and out from a mobile app or physical clock. Hours flow directly into payroll — no manual entry, no transcription errors, no end-of-week text chains.
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Pay-As-You-Go Workers’ Comp
Premiums calculated on actual payroll each period and remitted automatically. No large annual deposit. No year-end audit surprise. Especially valuable for businesses where seasonal hours — and therefore exposure — vary significantly.
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Retirement Plan Administration
We administer SIMPLE IRA, 401(k), and other plans through iSolved — contributions flow directly from payroll, no manual transfers. Helps you retain experienced foremen and full-time staff who have options.
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Payroll Tax Filing
We handle federal and state payroll tax deposits and filings — 941s, state returns, UI, and new hire reporting — so you’re never guessing whether something was filed on time.
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A Local Team That Knows You
Two offices — Mundelein, IL and Grafton, WI. A real person picks up when you call. Our team has worked with landscaping businesses in the Chicago metro and greater Milwaukee area for over 20 years. We know the seasonal rhythms because we live them too.

Need accounting, tax planning, and equipment depreciation strategy alongside payroll? Our sister company Accounting Freedom specializes in landscaping businesses. One call, both covered. Learn more about Illinois payroll tax requirements or Wisconsin payroll tax requirements for small businesses.

Ready to simplify payroll?

Your crew deserves to get paid right. Every time.

Let’s walk through your current payroll setup and show you what timekeeping, onboarding, and pay-as-you-go workers’ comp 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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