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Jeffrey Webb has extensive work experience in the aviation industry. Jeffrey started their career in 2000 with the United States Air Force, working as a Military Officer and KC-135 Pilot. Throughout their time in the Air Force, they held various roles, including Director of Operations, Chief Pilot/Chief of Flying Standards & Evaluations, Chief of the Air Mobility Control Team, and Assistant Director of Operations. Jeffrey also served as a T-6 Instructor Pilot. In 2021, Jeffrey joined Delaware Resource Group as a KC-135 Pilot Instructor and Scheduler.

Jeffrey Webb obtained a Bachelor's degree in Geography from the University of Georgia - Franklin College of Arts and Sciences. Jeffrey pursued further education and received a Masters degree in Military Operational Art and Science/Studies from Air University.