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Caleb Cowen has a diverse work experience starting from their current role as a Software Engineer II at Checkr, Inc. since December 2021. Prior to this, they worked as a Senior Consultant at Object Partners, Inc. from August 2020 to December 2021. Before that, they were a Senior Software Engineer at Cognizant from April 2019 to August 2020. From June 2017 to April 2019, Caleb worked as a Software Engineer at Allstate, and they briefly worked as a Self-employed Software Developer in 2017. In 2016, they completed a Back end software development program at the Turing School of Software & Design. Prior to that, they worked in various roles at Dart Container, Berry Plastics Corporation, and Discount Steel, LLC, gaining experience in operator, press assistant, and general laborer positions. Caleb also worked temporarily as a temp for Berry Plastics through Express Employment Professionals in 2013. Caleb has a strong background in software development and has worked in both consulting and corporate roles.

Caleb Cowen's education history includes attending the Turing School of Software & Design in 2016, where they obtained a Certificate of completion in Computer Software Engineering. Prior to that, from 2007 to 2009, they attended Murray State College, where they pursued General Studies.