General Skeen entered the Air Force in 1949, transferred to the US Army in 1953, and upon completion of Officer Candidate School that year was commissioned a Second Lieutenant in the Infantry. After serving as Platoon Leader in various Infantry and Airborne companies, he was awarded a Regular Army Commission as a Quartermaster First Lieutenant in 1958.

During most of his career, General Skeen held important Quartermaster mission-related command and staff positions. Key staff assignments included Director, Supply and Maintenance in the Office of the Deputy Chief of Staff for Logistics; Secretary of General Staff, US Army Computer Systems Command; and Assistant Deputy Chief of Staff for Logistics, US Army Europe and Seventh Army; and Secretary to the General Staff, US Army Computer Systems Command, Fort Belvoir; other important commands included Commander, US Army Troop Support Command, St. Louis; Commander Defense Industrial Support Center, Philadelphia; Commander, Defense Reutilization and Marketing Service, Battle Creek, Michigan; Commander, 88^th Supply and Service Battalion, Vietnam; Commander, Regional Support Activity, Military Region II, Vietnam; Commander, US Army Logistics Evaluation Agency at New Cumberland Army Depot; and Commander, Burtonwood Army Depot, England.

General Skeen played a pivotal role in launching the Quartermaster Corps into the automation era in the 1960s and 1970s, and later lent major support to the establishment of the Army Supply Excellence Award and the Army Supply Master Plan.