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Ben Crago has held multiple positions in the business sector since 2012. From 2012 to 2017, they ran a self-run boat cleaning business, B and B Boat Detailing. During this time, they also held an internship at Chris-Craft Corporation as an Industrial Engineer Intern, where they managed a Lamination project that saved the company time and money. In 2016, they took on an internship as a Sales Intern at Oyster Harbors Marine. From 2017 to 2018, they worked at Trux in various roles, starting as an Account Executive, then becoming a Senior Account Executive, Director of Sales, and finally, Sales Business Development. In 2022, they began working at MarketSpark, Inc. as the Director of Enterprise Business Development, and also took on a role as the Director Of Business Development at Soil Connect.

Ben Crago completed their Bachelor of Science in International Maritime Business from the Massachusetts Maritime Academy in 2018. After graduating, they pursued a Bachelor's degree in Maritime Studies from Singapore Experiential Learning in the same year.