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Rebecca Wynn has a diverse work experience in the military and joint operations. Rebecca began their career in 2015 as the Chief of C2 Operations at the 561st Joint Tactics Squadron. From 2018 to 2019, they served as the Deputy Chief of the 552 Group Weapons and Tactics at the 552 Operations Support Squadron. In 2019, they became the Chief Officer of the E-3G Fully Qualified Conversion Team. Starting in 2014, Wynn held various roles in the United States Air Force, including Instructor Section Lead and Instructor Senior Director for E-3G and E-3B/C/G Sentry (AWACS) aircraft. Rebecca was also the Assistant Director of Operations at the 552 Operations Support Squadron from 2020 to 2022. Currently, Wynn is the Chief of Air Plans at the Joint Enabling Capabilities Command, a position they have held since 2023.

Rebecca Wynn obtained their Bachelor's degree in Secondary Education and Teaching from Bloomsburg University of Pennsylvania. Rebecca pursued their education at the university from 2004 to 2007.