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J. Drew Bailey has a diverse work experience, beginning with the US Army in 2011. In this role, they served as Logistics Director, Operations Manager, and Area Manager, where they led 51 logistics specialists, was responsible for $7.5M of equipment, and managed a $200K budget. J. Drew was also selected by the colonel to serve as Airfield Control Group Leader and deployed 43,427 Soldiers and $1.5B of equipment to locations around the world. J. Drew then moved on to Amazon in 2017 as an Operations Manager Fellow, followed by Gartner in 2018 as a Business Development Manager and Account Executive. Currently, they are employed at Compass Laboratory Services as Chief Operating Officer and Director of Operations.

J. Drew Bailey attended the United States Military Academy at West Point from 2007 to 2011, where they earned a Bachelor of Science in Economics and Systems Engineering.