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Bobby Brown has a long and varied work history. Bobby began their career in 1991 with Target as Director of Operations. In 2000, they became the E-Commerce Project Marketing Manager at National Leisure Group, Inc. After that, they worked at Sugarloaf/USA as Marketing and Merchandising Manager from 2002 to 2006. In 2006, they were appointed President/Executive Director at the Stanley Museum. In 2007, they became a Sales Representative at Target Marketing of Maine. In 2008, they were hired as Regional Recruiting Manager at Colonial Life. From 2010 to 2016, they worked at PMWeb as Director, Sales & Operations. In 2016, they became Director, Sales NE at DefenseStorm. Finally, in 2017, they were appointed Director, Channel Partners and Strategic Sales at PMWeb - The World's Leading Capital Project Management Software.

Bobby Brown attended Bentley University from 2001 to 2002 where they received a Project Management Certification in Project Management.