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Bob Aitken began their work experience in 1983 at AMS Services, where they held the position of VP Vertafore Agency Markets. In the same year, they also joined Vertafore as VP Agency Markets. Later, in 2003, they became a Founding Partner at Mesa Fresh Mexican Grill. Additionally, from 2006 to 2008, they served as the President of the Philadelphia Lacrosse Association.

Bob Aitken attended William & Mary from 1976 to 1981, where they earned a BBA in Accounting.