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Jon Glidewell began their work experience in 2011 at Kelly Services, where they held various roles providing technical support for Apple iOS. Jon started as an Apple Tier 1 iOS Technical Support and later advanced to become an Apple iOS Senior Advisor, Technical Support Tier 2. In 2015, Glidewell joined cyberMIND Corporation as an IT Level 1, but left the position after six months. From 2017 to 2022, they worked at Eaton as a Senior Technician. Currently, Glidewell is employed at ProAssurance as a System Engineer 1, starting in October 2022. Additionally, Glidewell has been the Owner of Glidewell Technologies since 2008.

Jon Glidewell attended Kalamazoo Valley Community College from 1999 to 2002, where they pursued and received an AAS degree in Microcomputer Technician.