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Courtland Hollingsworth started their work experience in 2007 as a Field Technician at Cox Communications, where they worked until 2009. Courtland then worked as a Warehouse staff at All points food service and supplies from 2009 to 2010. Courtland subsequently joined Clearwire as a Tech Support from 2010 to 2011. From 2011 to 2013, they worked at Switch SuperNAP, first as a NOC Technician and later as a Jr. Admin. Finally, in 2022, they became the Lead Help Desk Technician at Switch.

Courtland Hollingsworth attended ITT Technical Institute-Henderson from 2010 to 2013, where they were working towards an Associate Degree in Computer Systems Networking and Telecommunications.