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Bob May has extensive work experience spanning over several decades. Bob began their career as a Director at TAC Worldwide Companies in 1984, a role they held until 2006. Bob then transitioned to become the Director at TAC Worldwide, where they continued until 2006. In 2006, Bob joined Algomod Technologies as a Director, before moving on to Workway, Inc. in 2007. At Workway, Inc., they served as the Vice President and General Manager of the VMS Group until 2011. Bob then assumed the position of President at inSync Staffing in 2011. With their broad experience and leadership roles, Bob has demonstrated their ability to excel in various professional capacities.

Bob May attended the Questrom School of Business at Boston University from 1977 to 1981, where they earned a Bachelor of Science degree in Marketing and Operations Management. Bob then pursued further education at Boston University from 1982 to 1983 and obtained a Master of Urban Affairs degree. However, no specific field of study is mentioned for their Master's degree.