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Dennis Kasper has extensive work experience in the financial sector. Dennis began their career as a Financial Analyst at Forest City Enterprises in 1995 and stayed with the company until 1996. Dennis then joined Clearstead in 1997, initially holding the roles of Managing Director Information Technology and Managing Director, with no specified end dates for either position.

Dennis Kasper completed their high school education at Lorain Catholic High School. Dennis then went on to pursue a Bachelor of Science in Business Administration (BSBA) with a focus on Finance at John Carroll University from 1991 to 1995. Afterward, they obtained a Master of Science in Management - Information Systems (MSM-IS) from the Weatherhead School of Management at Case Western Reserve University, where they attended from 2000 to 2002.