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Jason Webb has extensive work experience starting in 1990 when they joined the United States Air Force as a USAF Officer. Jason worked there until 2020, when they retired after a successful career. In 2010, they joined Pacific Crest Insurance as a Principal and later became the Director of Marketing until 2012. In 2020, they became the Chief Executive Officer of Pacific Crest Services, where they are currently employed.

Jason Webb has a Master of Business Administration (M.B.A.) from Colorado State University, which they obtained from 2006 to 2009. Prior to this, they completed a Bachelor of Science (B.S.) in Business Administration and Management, General from Lewis Clark State College between 1994 and 1998.