Who must carry it in Kentucky
Every employer with one or more employees must carry workers' compensation; agricultural employers and a few other categories are exempt.
Who counts as an employee
Part-time and seasonal employees count, and out-of-state employers must cover work performed in Kentucky. The label on the paycheck does not settle it: Kentucky applies its own employee test, and a worker who fails it is an employee for workers' compensation no matter what the contract says.
Owners, officers and LLC members
Sole proprietors, partners and LLC members can choose to be covered. An employee may reject coverage only by filing a Form 4 waiver. The election is made on the policy and affects both coverage and premium, so decide it before the policy is bound rather than at audit.
The day you hire
CoverMatch quotes workers' compensation from the first employee, with pay-as-you-go billing through most payroll companies where a carrier offers it, so the policy can start the week you hire without a large deposit. Add the policy to your wallet and the live certificate is ready for the general contractor or client who asks for proof.
If you go without
Uninsured employers face fines per day of non-compliance, can be enjoined from operating, and are liable for benefits. The specific amounts and procedures are in the statute and on the agency page linked above; they change, and the licensed agent who reviewed this page checks them on each update.