CCMSgt Shupp joined the U.S. Air Force in 1966. After Basic Military Training, he attended the Air Force Security and Law Enforcement Academy, graduating in 1966.

His first assignment was to a Strategic Air Command Base in Cheyenne, Wyoming from 1966-1969 and South Korea from 1969-1971. After his discharge from the active Air Force, he attended college and received an Associate Degree of Arts in Business Administration from Northampton Area Community College in Bethlehem, Pa and a Bachelor of Arts in Political Science from East Stroudsburg University, Pa. in 1974.

Chief Shupp was employed with the Commonwealth of Pennsylvania from 1975 until his retirement in 2004.  He retired as the Director of Administration for the Pa. State Employees’ Retirement System.

Chief Shupp joined the Pa. Air National Guard in 1982 became a member of the 193rd Special Operations Wing and held several positions in the Security Police Squadron and was appointed Chief of the Squadron in 1999.

Chief Shupp was selected as the Command Chief Master Sergeant of the Pa. Air National Guard and installed in July of 2005.  He is currently stationed at Headquarters, Fort Indiantown Gap and represents over 3600 enlisted Air National Guard members throughout 3 wings in Penna. He serves in the capacity of the Senior Enlisted Advisor for all Air National Enlisted Guard members to the Adjutant General of Pennsylvania.

He has been involved in various deployments throughout the world, including Desert Shield/Desert Storm and was militarily activated after 9-11 for 1 and ½ years.

He has received various awards, medals and ribbons throughout his military service, including the Air Force Meritorious Service Medal with 1 Oak Leaf Cluster, both the Air Force and Army Commendation Medal, the Air Force Achievement Medal and the Pa. Commendation Medal.  He also received the Kuwaiti Liberation Medal and the Global War on Terrorism Medal.