Kasold is a 1973 graduate of the U.S. Military Academy and was commissioned as an Air Defense Artillery Officer. He transitioned to the Judge Advocate General Corps after receiving his Juris Doctorate from the University of Florida Holland Law Center in 1979. He served in a variety of JAG positions including Associate General Counsel, Office of the Army General Counsel.

After retiring from the Army in 1994, he worked as a litigation attorney for the law firm of Holland & Knight, followed by service as the Chief Counsel for the Senate Rules Committee and the Offices of the Secretary and Sergeant at Arms for the Senate. In 2003, he was appointed as a judge on the U.S. Court of Appeals for Veterans Claims where he served until 2016, including service as the Chief Judge.

He most recently served as the Acting President and COO of the PENFED Foundation.