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Bobby Degregorio has extensive work experience, with their most recent role being the Vice President of Business Development at ESI Group USA since February 2023. Prior to this, they were the Business Development Manager for the South East Region at the same company from August 2021 to February 2023. Bobby also has a background in the United States Air Force, where they served as an IMA to HAF A4LX and later as a Logistics Readiness Officer and Mission Support Group Commander from November 2021 to present, and from July 1996 to January 2022, respectively.

Bobby Degregorio began their education in 1991 at Charleston Southern University, where they pursued a degree in Criminal Justice and Political Science. Bobby completed their undergraduate studies in 1995. In 2012, they attended the Air Command and Staff College for Professional Military Education, specializing in Military and Strategic Leadership. Following that, from an unspecified start year to 2016, Bobby enrolled in the USAF Air War College, though no specific degree or field of study is mentioned. Finally, in 2017, they pursued a Master's degree in Military Studies with a focus on Joint War Fighting at American Military University, which they completed in 2018.