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Josh Dremsa has a diverse work experience, starting with their current role as an Associate Pastor at True Life Church since May 2022. Prior to that, they worked as an Accountant at Cover Whale from April 2021. Before their role at Cover Whale, Josh held positions at HNI Risk Services, where they served as a Staff Accountant from April 2019 to April 2021 and as an Accounting Specialist from January 2017 to April 2019. Josh also worked as a Bookkeeper at Marriott Construction from July 2016 to November 2016. Josh's earliest documented work experience was as an Invoicing Legal Assistant at J Peterman Legal Group Ltd. from October 2011 to July 2016.

From 2012 to 2016, Josh Dremsa attended the University of Wisconsin-Whitewater and pursued a Bachelor of Business Administration (BBA) degree in Accounting.