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Rob Stein began their career in 1997 as a Computer Engineer at Verizon. In 1999 they moved to Digex, where they served as a Sr. Internet Systems Administrator. In 2004, they began working at The Analysis Group, LLC and Keane as a Computer Engineer. In 2008, they started working at Vandelay Technologies in the same role, and also became Owner / CFO of SRC Technologies.

Rob Stein attended Springbrook from 1990 to 1993 and then the University of Maryland from 1993 to 1997, where they earned a Bachelor of Science in Electrical Engineering.