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Will McSwain has a diverse work experience background. Will is currently the Director of Tournament Operations for PBR Baseball at Prep Baseball Report. Prior to this role, they worked as an Umpire at Perfect Game USA from June 2019 to June 2022. Will also previously served as a Substitute Teacher at Kelly from August 2018 to May 2020. Additionally, they worked as an Umpire at USSSA from May 2018 to May 2020. Furthermore, they gained experience as a Baseball Coach for York Post 66 Legion Baseball at The American Legion from May 2018 to July 2019. Will started their professional journey as a Maintenance Worker at York School District No 1 from June 2015 to August 2016.

Will McSwain completed their Bachelor of Science degree in Physical Education Teaching and Coaching from Erskine College between 2016 and 2020. Subsequently, from 2020 to 2021, they pursued a Master of Business Administration (MBA) degree at Anderson University (SC).