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Jeremy McCaslin began their work experience in the insurance industry as an Account Manager for aviation accounts at Van Beurden Insurance Services from April 2000 to September 2004. Jeremy then joined Aviation Insurance Services of Utah, Inc. as an Assistant Vice President specializing in aviation insurance from September 2004 to May 2006. Following that, Jeremy worked at McGriff, where they held various roles, including Account Executive, Assistant Vice President, Vice President - specializing in aviation insurance from June 2006 to September 2010. Jeremy then became the President of the Aviation Practice at McGriff in October 2010 and later progressed to the role of Regional President in February 2022.

Jeremy McCaslin attended the University of Washington from 1998 to 2002, where they did not obtain a degree or specify a field of study. Jeremy also obtained the Certified Aviation Insurance Professional (CAIP) certification from the Aviation Insurance Association in May 2011.