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Ashley Boiardi has a diverse work experience spanning different industries. Ashley started their career at Lola's in 2005, where they worked as a Manager for six years. In 2011, Ashley joined Top It Off Accessories as a Retail Manager & Wholesale Associate and remained in this role until 2014. Later in 2014, they joined Regan Communications Group, where they held multiple roles over the years. Initially, they served as an Executive Assistant to the President and later became the Chief of Staff at Regan Communications Group. Currently, Ashley holds the position of President at Regan Communications from November 2022 till date.

Ashley Boiardi attended Framingham State University from 2007 to 2011, where they obtained a Bachelor of Applied Science (B.A.Sc.) in Fashion Merchandising. Ashley also earned a Bachelor's Degree in Fashion Merchandising during the same time period.