Who must carry it in Massachusetts
Every employer with one or more employees, full- or part-time, must carry workers' compensation; domestic employees working sixteen or more hours a week are included.
Who counts as an employee
Part-time, seasonal and family employees count. Sole proprietors and partners are not required to cover themselves. The label on the paycheck does not settle it: Massachusetts 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
Corporate officers who own at least a quarter of the company may exempt themselves by filing with the Department; sole proprietors and partners may elect coverage. 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 Department issues stop-work orders with daily fines until coverage is in place, and uninsured employers are barred from public contracts. 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.