State law and your employee count determine when you should have workers' comp, but practical triggers usually come earlier. A landscaping business might plan to hire in spring but need coverage in winter to bid on commercial contracts that require proof of insurance upfront. Use this checklist to see whether you need to get coverage sooner rather than later.
You likely need workers' comp earlier if you:
- Hire anyone: Part-time, seasonal and temporary workers all count. One person on payroll can trigger the requirement.
- Get a COI request: A client or property owner asking for proof means you need it now, not later.
- Work onsite: Clients won't let you or your crew on commercial properties without proof of coverage.
- Do hands-on work: Construction, cleaning, delivery, installation and repair all put you in coverage territory.
- Work in a one-employee state: Your first hire triggers the requirement in many states. No grace period.
- Add workers to your operation: The moment you stop working solo and start supervising others, the rules change.
- Own a business in a coverage-mandatory state: Some states require sole proprietors, partners and LLC members in certain industries to carry it.




