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.

In one sentence: Payroll Freedom provides payroll for landscaping and snow removal companies in Illinois and Wisconsin — including electronic onboarding for seasonal crews, mobile timekeeping, and pay-as-you-go workers’ comp — 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 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 contributions through payroll

Direct deposit & pay stubs

See how it works

Watch: How We Handle Landscaping Payroll in Under 2 Minutes

In this video (1:43): electronic onboarding for spring crews, mobile timekeeping, summer and winter payroll cycles, pay-as-you-go workers’ comp, and retirement plans.

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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, so there’s no year-end true-up surprise.

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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. Many small landscaping businesses don’t offer 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 and different pay rates 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 is faster and cleaner.

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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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Seasonal & Snow-Season Payroll

Summer and winter payroll cycles run on the same platform, so your landscaping crew and your snow removal crew are each paid and reported correctly — no spreadsheet required.

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Seasonal Offboarding & Rehire

Streamlined offboarding when the season ends, and quick rehire setup when returning crew members come back. No starting over from scratch every spring.

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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 for businesses where seasonal hours — and therefore exposure — vary significantly. Available as an add-on at $10 per payroll.

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Retirement Contributions Through Payroll

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

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

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 12-person crew on a bi-weekly Core plan pays $104.20 per payroll.

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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