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Bob Roswell has a diverse work experience spanning several decades. Bob started their career at System Source in 1981, where they held the position of VP. Their role as VP continued until 2008. In 2010, they joined Baltimore Angels as a Member and remained there until 2013. In 2014, they joined the National Electronics Museum as a VP, a role they held for a year.

Bob Roswell attended Yale University from 1976 to 1980, where they obtained a Bachelor of Science degree in Computer Science. Prior to Yale, there is no available information about their education.