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Chantel McCaskill has a diverse work experience starting in 2013. Chantel began their career at Saint Xavier University as a Media Services - Quality Assurance, where they were responsible for troubleshooting equipment, maintaining and cleaning devices, and updating software. In 2015, they worked at Best Buy as a Consultant Agent and at Geek Squad as a CA, where they assisted clients with their device problems and installed software and hardware. In 2016, they worked at Apple as a Technical Specialist, where they were responsible for trouble shooting mobile devices, supporting customers, and suggesting solutions for issues. Chantel also worked at BlackBeltHelp as a Technical Support Analyst I.

Chantel McCaskill earned a Bachelor's degree in Computer Studies from Saint Xavier University between 2012 and 2016.