Command Sgt. Maj. Kevin Flickinger enlisted in the Army in May 2002 as a Cryptologic Linguist. He attended basic training at Fort Jackson and Advanced Individual Training at the Defense Language Institute and Goodfellow Air Force Base. He reclassified to Cyberspace Operations in 2015.

His assignment history includes Command Sergeant Major, Cyber Protection Brigade; Command Sergeant Major, Cyber Training Battalion; Command Sergeant Major, 2d Cyber Protection Battalion (Provisional); First Sergeant, Headquarters & Alpha Company, Cyber Training Battalion; First Sergeant, Alpha Company, 782d Military Intelligence Battalion; SOT-A Team Leader and Advanced Collection and Training Team NCOIC, 5th Special Forces Group (Airborne); Signals Intelligence NCOIC, Asymmetric Warfare Group; and Mission Operations NCOIC and Command Language Program Manager, 224th Military Intelligence Battalion.

He holds a Bachelor of Arts in English Literature from the University of Michigan, and a Master of Business Administration in International Management from the University of Phoenix.
CSM Flickinger's awards and badges include the Legion of Merit, Bronze Star Medal, Meritorious Service Medal (3 OLC), Army Commendation Medal (3 OLC), Army Achievement Medal, Armed Forces Service Medal, Combat Action Badge, and Parachutist Badge.