Who must carry it in Virginia
An employer with more than two employees regularly in service must carry workers' compensation; part-time, seasonal, family and temporary employees and corporate officers all count.
Who counts as an employee
Contractors count the employees of their uninsured subcontractors, so a two-person contractor who hires a sub can cross the line. The label on the paycheck does not settle it: Virginia 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 unless they elect coverage; corporate officers and LLC members count toward the threshold but may exclude themselves by filing with the carrier. 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 civil penalties, possible cease-and-desist orders, and liability for benefits plus attorney fees. 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.