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Robert Matthews started their career in 1985 as a Lab Support Design Engineer at Motorola, where they designed test labs and networks, performed software testing, and developed testing strategies. Robert then worked at St. Peter's RC School as a Middle School teacher from 2002 to 2003. Robert later joined Adelphia as a Tech Support representative from 2003 to 2005. Robert then spent several years at Synacor, where they held various roles such as QA Analyst, Senior QA Analyst, QA Integration & Release Supervisor, Lead Quality Engineer / Applications Administrator. At Synacor, they supported multiple teams in developing web-based software applications and was responsible for installation, configuration, and standardization of issue tracking and wiki applications. Robert also initiated standard workflows and uses of the wiki company-wide. Robert joined LocalEdge in 2014 as a Quality Analyst, where they focused on product lines and worked with SEO, SMM, and Reputation Management. Most recently, they joined a company looking for career growth in 2017 as an Experienced computer professional.

Robert Matthews attended Lakeview High School, although the specific years are unknown. After high school, they enrolled in the Community College of the Air Force from 1973 to 1976, earning an Associate of Arts (AA) degree in special electronics. Subsequently, from 1977 to 1981, they studied at the University of Northern Colorado, where they obtained a Bachelor's degree in Elementary Education.