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Alan "Wooly" Wooldridge has over 12 years of work experience. Alan "Wooly" began their career in 2008 as Manager of the Aeromedical Evacuation Operations Branch for the US Air Force. In 2013, they joined TRI-COR Industries, Inc. as a Level II Help Desk Specialist. In 2017, they became a Project Manager-ERC EHR Sustainment for Smartronix, LLC. Most recently, in 2020, they joined Ellumen, Inc. in the same role.

Alan "Wooly" Wooldridge received an Associate of Science degree in Health Services/Allied Health/Health Sciences, General from the Community College of the Air Force between 2008 and 2010.