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Wilkerson Jim's work experience begins in 1984 as an Airframe Mechanic in the US Army. From 1987 to 1998, they worked as a Pilot in the Army National Guard. In 1995, they became a Charter Pilot at Bijan Air until 1999. From 1999 to 2016, Jim worked at Air Methods, starting as a Line Pilot and progressing to roles such as Lead Pilot, Area Aviation Manager, and Regional Aviation Director. Since 2016, they have been with CHI Aviation, first as Chief Pilot and currently as the Director of Operations.

Wilkerson Jim completed their education with a B.S in Aviation Technology from Purdue University, where they studied aviation from 1993 to 1995. Prior to that, they attended the Community College of Beaver County from 1989 to 1992 and obtained an A.A.S in Professional Piloting with a focus on aviation. In addition to their educational background, Wilkerson Jim holds certifications such as ATP Helicopter from FAA Safety Team (FAASTeam) and Commercial Airplane Instrument. However, specific details regarding the months and years of obtaining these certifications are not provided.