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Gregory Bailey has a diverse work experience spanning over three decades. Gregory started as a Slitter Operator/Extra Press Help at Stone Container Company in 1987. Gregory then worked as a Heavy Equipment Operator at 117 Civil Engineer Squadron. Gregory joined the 117 Resource Management Squadron in 1987 and worked as a Packing and Crating Technician. In 1989, they were NCOIC of Warehouse at 117 Logistics Readiness Squadron. Gregory then joined 117 Civil Engineer Squadron again as NCOIC of Material Control. Gregory worked at 117 Air Refueling Wing as Traffic Manager from June 1993 to April 2001 and as Munitions Maintenance Mechanic at 117 Aircraft Maintenance Squadron from August 2001 to August 2003. Gregory then worked as Production Control Manager and NCOIC Material Control at 117 Civil Engineer Squadron before joining the Air Force National Guard as Facilities Manager in August 2007, where they worked until October 2017. Since January 1997, they have also been President at Bailey Consulting Services, where they provided logistical and training consultation services with a focus on Hazardous Materials Familiarization and Certification and facilitated training courses.

Gregory Bailey earned an Associate of Arts degree in Art/Art Studies, General from Faulkner University in 1995, followed by a Bachelor of Applied Science in Human Resources Management/Personnel Administration, General from the same university in 1996. Gregory also earned three Associate of Science degrees from the Community College of the Air Force: one in Logistics, Materials, and Supply Chain Management in 1995, another in Maintenance Production Management in 2011, and a third in Transportation/Mobility Management in 2012.