An employee of my company (I am sole proprietor) holds the contracting license. If he leaves the company is he entitled to anything?

Assuming you are referring to a Contractors license issued by the Department of Professional and Occupational Licensing in VA, to qualify for the license, the company must have a responsible member of management, meet certain financial requirements, and have an employee that has either passed a test given by DPOR on contracting, or is grandfathered, referred to as a designated employee.    If you are saying that the employee who is leaving was the one who passed the test, you would still keep your license, but you must report to the contracting board that he has left and you have a certain amount of time to designate a new person that has either passed the test, or grandfathered.  He is not entitled to any money from you just because he was your designated employee. but may have a right to monies owed under his contract, depending on your agreement with him.