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Bob Leavitt has a diverse work experience, starting in 2010 as an Inbound Sales Representative at Great Falls Marketing and working there until 2013. In 2013, they joined Aerus as a Sales Consultant. In 2014, they worked as a Banker at Bank of America until early 2015. In February 2015, Bob became a Senior Sales Executive at Cirrus Systems, Inc. Concurrently, they also worked as an Intel Sales Representative at ActionLink in January 2015. Additionally, they had a role as a Sales Rep at Cirrus LED Systems, although the start and end dates are unspecified.

Bob Leavitt earned an Associate's degree in Specialized Sales, Merchandising and Marketing Operations from Southern Maine Community College, which they attended from 2008 to 2010. Bob later returned to the same institution in 2015 to study Computer Science, but the end year for this program is not provided.