Ross has had a diverse career. He has a Structural Engineering degree from Milwaukee School of Engineering, but gave up the career shortly after graduating from college. Beginning in 1997, Ross began officially working in IT, implementing and supporting a paperless work order system for a Natural Gas Utility in Illinois. Since then, Ross has spent his years teaching and managing data networks. Ross spent 7 years at University of Wisconsin Hospitals and Clinics, supporting and managing the large enterprise network. He now has returned to teaching at Madison College in Madison, Wisconsin.