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Rob Bailey has a diverse work experience in the field of information technology. Rob started their career at Canyons Resort in 2007, serving as the IT Operations Manager until 2012. In 2011, they joined Global Events Group as an IT Director, leading the company's technology initiatives for a year. In 2012, Rob joined Illinois State University as an IT Project Manager and later became the Executive Director of Student Affairs Information Technology in 2015.

From 1994 to 1998, Rob Bailey attended Oral Roberts University. However, the degree and field of study pursued during this time are unknown.