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David Webb has extensive work experience in the aviation industry. David began their career in 1971 in the US Air Force and served until 1992. After retiring, they worked as a pilot for various airlines, including Northeast Express Airline, Business Express Airline, and Oklahoma Executive Jet Chart, Inc. David then served as the Chief Pilot for Western Air Express and State of Wisconsin. David's most recent role was as the Chief Pilot for Wisconsin Aviation, Inc.

David Webb completed their Bachelor's degree in Biology from Culver-Stockton College from 1974 to 1975. Following this, they pursued higher education and obtained a Master's degree in Human Relations and Supervision with a focus on counseling and personnel management from Louisiana Tech University between 1986 and 1987.