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Richard Dearing has extensive work experience, with their most recent position being at Net Health. Richard started at Net Health in 2006 as the Manager of Technical Support and held that role until March 2022. From February 2022 onwards, they transitioned to the role of Manager of Site Reliability Engineering. Prior to working at Net Health, Richard completed an internship at Thompson Machinery in 2004 as a Helpdesk Technician. During their internship, they were responsible for troubleshooting desktop software and hardware issues, as well as user maintenance for a server farm.

Richard Dearing attended Middle Tennessee State University (MTSU) from 2003 to 2005, where they earned a Bachelor's degree in Computer Information Systems.