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For tree service owners

When is it time to hire my first employee?

Short answer

Hire when you are turning down paying work or working unsafe hours, and you can cover the full cost of the person. That cost is more than wages: it includes payroll taxes, workers' compensation, training, tools and time. Run the numbers first, and talk to an accountant. This is not legal advice.

By Umair Nawaz. Published October 25, 2026. General information, not legal, tax or insurance advice.

The longer answer

Many owners start with day help or subcontractors, then hit a point where they need someone steady. Signs it may be time: jobs are waiting for weeks, you are doing the work of two people, or safety is suffering because you work alone.

Before you hire, count the full cost. Wages are only the start. Add employer payroll taxes, workers' compensation, training, gear, and the extra time you will spend managing. Our hiring cost calculator lets you enter your own figures and see the total.

Next, ask whether the extra pair of hands will make you more money. A good ground person lets a climber work faster and safer. If that means two more jobs a week at a fair margin, the hire can pay for itself. If you have no extra work to give them, wait.

Think about the kind of worker you need. A trained, careful person costs more but may save you injuries and rework. Check references, test skills on a real job and set clear safety rules from day one.

Do the paperwork right. Employee rules, tax withholding and workers' comp requirements vary by state, so ask an accountant or employment lawyer.

This is a short explanation, not legal or tax advice.

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