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Bob MacDonald began their work experience in the late 1980s as a Graphic Artist at Strawberries Records & Tapes and Strawberries Inc. Bob then transitioned to become the Northeast Sales Manager at Priority Records from 1993 to 2001. In 2002, they worked as an Account Executive at WXRV- 92.5 The River until 2004. From 2005, Bob MacDonald worked at the Daily News of Newburyport/ The Salem News as the Advertising Sales Manager and Director of Sales for the Readings and Newburyport magazines. Most recently, they have been the Director of Magazine Sales at North Of Boston Media Group since 2016.

From 1981 to 1986, Bob MacDonald attended Framingham State University, where they pursued a field of study in Communication and Media Studies. The information does not specify whether they obtained a degree during this time.