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Dick Matthews has a diverse work experience spanning several industries. Dick started their career at Direct Home Advertising, Inc. in 1988, where they served as a VP of Sales and successfully managed a sales force covering MA, NH, and RI, resulting in revenues exceeding $10 million per year. In 2004, they became a Volunteer-Outdoor Program Committee Chair for the Boston Minuteman Council of the Boy Scouts of America, primarily focusing on planning Boy Scout outdoor activities. Following this, they joined Valassis in 2007 as a Market Manager, actively managing the North East Metro Boston Market and achieving a personal sales revenue of $398,000, with the entire market sales revenue exceeding $1 million in 2011. Dick then transitioned to Spectrum Marketing Companies in 2011, taking on the role of Director of Business Development, where they consulted on strategic marketing, business expansion strategy development, and budget optimization. In 2013, they became an Executive Board Member for the Boston Minuteman Council, BSA. Additionally, during their tenure at the Boston Minuteman Council, they also served as the Chairman for the SOAR 2012 Scouting's Outdoor Adventure on the River, successfully setting the Guinness World Record for the longest Pinewood Derby Track and organizing over 150 hands-on stations for Scouts to experience.

Dick Matthews attended Brighton High School but did not graduate. No further information is provided regarding their education history.