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Bobby Webb has a long and varied work experience. Bobby began their career in 2014 as Managing Director at 1st Special Warfare Training Group (Airborne), where they supervised the training and quality of over 1,400 students per year from the U.S. and 30 foreign countries. In 2016, they moved to United States Army Special Operations Command as a Force Modernization Integrator, where they were an onsite integrator for equipment modernization and personnel structure efforts between USASOC and HQDA. In 2018, they returned to America's First Corps (I Corps) as a Program Manager, leading business development teams across multiple locations in Southeast Asia. In 2021, they moved to U.S. Special Operations Command Central (SOCCENT) as Chief Of Staff (JSOAC), directing operations for an organization with over 1,000 employees dispersed across seven countries. Finally, they are currently working as Security Operations Manager at Allure Security and as a Cyber Defense Intern at Centers for Medicare & Medicaid Services.

Bobby Webb obtained a Bachelor of Science in Criminal Justice from the University of North Georgia between 1998 and 2002. Bobby then went on to obtain a Master of Science in Administration from Central Michigan University between 2012 and 2014.