CW4 Reginald Oliver

Chief Digital Transformation Officer, Capability Program Executive, Aviation

U.S. Army

CW4 Reginald “Reggie” Oliver attended Warrant Officer Candidate School at Fort Rucker, Alabama, in 2008. After completing the Warrant Officer Basic Course, AH-64D Apache Advanced Qualification Course, and U.S. Army Rotary Wing Aviator Course in 2010, he was assigned to Bravo Company, 1st Battalion “Wolfpack,” 82d Combat Aviation Brigade (CAB), 82nd Airborne Division, Fort Bragg, North Carolina, deploying to Afghanistan.

In 2014, after graduating the Aviation Maintenance Officer Course and AH-64D Maintenance Test Pilot Course, he was assigned to Charlie Company, 1st Battalion, 82d CAB, 82nd Airborne Division, Fort Bragg, North Carolina, serving again in Afghanistan as a Maintenance Test Pilot. Following his second Afghanistan tour (2014–2015), he completed the Warrant Officer Advanced Course and in 2016 became a Maintenance Test Pilot with Alpha Company, 1st Battalion “Vipers,” 3d Aviation Regiment, 12th CAB, Katterbach, Germany.

From 2017 to 2019, Reggie served as Production Control Officer-in-Charge, Delta Company, 1st Battalion, 3d Aviation Regiment, 12th CAB, Katterbach, Germany, overseeing sustainment for 24 AH-64D Apaches, 6 CH-47F Chinooks, and associated equipment. In 2019, he moved to Delta Troop, 1st Squadron “Saber,” 17th Cavalry Regiment, 82d CAB, Fort Bragg, North Carolina, as Quality Control Officer-in-Charge, Senior Technical Inspector, and fleet database administrator.

In 2020, while deployed to Kuwait and the Northern Arabian Gulf, he conducted shipboard operations with the U.S. Navy and authored an ESB-3 class vessel SOP for attack helicopter maintenance. After redeployment in 2021, he completed Maintenance Test Pilot Examiner certification and was reassigned to 1st Battalion “Wolfpack,” 82d CAB, 82nd Airborne Division, Fort Bragg, North Carolina, serving as the Battalion Aviation Maintenance Officer during deployments to Iraq and Syria.

In 2022, Reggie was assigned to 3d Battalion “Sentinels,” 351st Aviation Regiment, 166th Aviation Brigade, 1st Army Division West, Fort Hood, Texas, as a MTP Observer/Coach Trainer and Battalion AMO supporting Army National Guard and Army Reserve aviation units. He later served as Brigade Aviation Maintenance Officer, Headquarters and Headquarters Company, 166th Aviation Brigade, 1st Army Division West, Fort Hood, Texas. During his time in Texas, he twice attended the Artificial Intelligence Strategic Broadening Seminar at the U.S. Army Research Lab and worked with the U.S. Army Artificial Intelligence Integration Center (AI2C) on AI application implementation for aviation readiness. In 2025, he joined Headquarters, Capability Program Executive (CPE) Aviation as the Primary Advisor for AI and Sustainment, and in 2026 became the CPE Aviation Chief Digital Transformation Officer (CDTO), leading enterprise-wide digital transformation efforts.

CW4 Oliver has a Bachelor of Science degree in Finance from the Florida State University (2007) and a Master of Business Administration degree from the Pennsylvania State University with a concentration in Public Administration (2025).

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