Who must carry it in the District of Columbia
Every employer with one or more employees working in the District must carry workers' compensation, including part-time and temporary staff.
Who counts as an employee
Casual and part-time employees count, and coverage follows where the work is performed: a Maryland or Virginia business with staff working in the District needs District coverage. The label on the paycheck does not settle it: the District of Columbia 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 and partners are not employees and may elect coverage; corporate officers are employees unless excluded in writing. 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
The Office of Workers' Compensation can fine an uninsured employer per day of non-compliance, and the employer is liable for benefits and legal costs. 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.