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Chester Cramer began their work experience in 2007 as a firedog PC Technician at Circuit City. Chester then transitioned to an IT Support Technician role at Maccaferri from 2008 to 2010. In 2010, they worked as a Tier 2 Technical Support at GDC. In 2011, they worked at three different companies: U.S. Silica Company as a Systems Engineer, Affinity Network Solutions as a Windows Migration Technician, and Sterling Computers as a Lead Refresh Technician. At Affinity Network Solutions, they played a key role in transitioning a company of 25,000 employees to a new Windows 7 image. At Sterling Computers, they provided support for troubleshooting and quality control for a government client's PC refresh project.

Chester Cramer attended Kaplan University from 2005 to 2007, where they obtained an Associate's Degree in Computer Forensics. Currently, they also hold an ITIL Foundation certification from AXELOS Global Best Practice.