After graduating from Delmar High School, Bob attended Salisbury State College and graduated in 1980. Bob attended the University of Baltimore School of Law and graduated in 1986. Immediately after passing the bar exam in 1986, Bob joined the law firm of Cullen, Clark, Insley & Hanson in Salisbury and practiced with that firm until its merger with Laws and Laws, PA. Bob is currently a partner at Laws, Insley & Benson, P.A.

Bob is engaged in a general practice of law with an emphasis in commercial and business law, banking law, real estate law, estates and trusts law and municipal law. Bob has represented the Town of Delmar, Maryland and the Town of Mardela Springs for more than 25 years. In his practice Bob appears in both the District and Circuit Courts in Maryland and has handled appeals in both the Court of Special Appeals and the Court of Appeals of Maryland.

Bob is a member of the Maryland State Bar Association and the Wicomico County Bar Association. Bob is a Past President of the Salisbury Wicomico Lions Club.