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Ken Bailey has a diverse work experience spanning over several decades. Ken started their career as a Distribution Operations employee at Exxon Chemical Company in 1984. Ken then moved up to become a Senior Supply Planner in 1995. In 1998, Ken joined Rec Warehouse, LLC as the Director of Inventory Control and later became the Vice President of Operations. During their tenure, they managed various departments, negotiated settlements, and played a key role in restructuring the company. In 2014, Ken transitioned to the Montana Office of Public Instruction, where they served as Assistant Superintendent of Operations and eventually became the Chief Financial Officer in 2018.

Ken Bailey earned a Bachelor of Science degree in Psychology from Penn State University between 1972 and 1976. Later, they pursued a Master of Business Administration (MBA) specializing in Business Logistics from Penn State University, which they completed between 1978 and 1980.