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Kirk Olesick began their work experience in 2013 as a Civil Servant at Olmsted Township, where they served until February 2017. In February 2017, they joined Middough Inc. as a Project Accountant. In January 2018, they transitioned to Baumgarten & Company, LLP CPA as a Tax Assistant, but left in April 2019.

Kirk Olesick earned a Bachelor's degree in Accounting and Finance from Tiffin University during the years 2012 to 2016.