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Joe Gregory's work experience includes roles at various companies in the technology industry. Joe worked at Grapevine MSP as the President, starting in 2009. Prior to that, they were the Vice President of CharTec Solutions at ARRC Enterprises, Inc., where they focused on growing the Southern California CharTec offering and improving client information technology systems. Joe also served as the In-House Service and Repair Supervisor, where they revolutionized break-fix service operations and increased profits. Before that, they were an Authorized Technician III, responsible for network infrastructure installation, management, and repair. Joe also worked as an IT Systems Administrator at Maricopa Unified School District, where they prioritized problems and requests, performed technical installation and maintenance, and organized department user groups.

Joe Gregory attended MUSD from 1995 to 1999, where they did not pursue a specific degree or field of study. Later, from 2007 to 2009, they attended Managed Services Provider University (MSPU), specializing in IT Managed Services and Sales Training.