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Jack Caldwell has a diverse work experience. Jack started as a Salesperson at Corkscrew Wine & Spirits in October 2018 and worked there until May 2019. Prior to that, they interned at Midlands Management Corp. from July 2015 to August 2019. In January 2021, they became a Data Analyst at the Oklahoma State Department of Education, where they worked until June 2022. Currently, they serve as a Business Development Manager at Darr Equipment Co, starting in June 2022.

Jack Caldwell attended the University of Oklahoma from 2015 to 2020, where they earned a Bachelor of Arts degree in Economics.