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Caroline Bigelow's work experience includes a senior producer and strategic team lead role at Haystack Needle LLC, a marketing strategy consultant role and later a VP of marketing role at Longview Strategies, a seasonal admissions reader role at Northeastern University, a senior marketing communications manager role at Boston Children's Hospital, and an account director/partner role at Copper Hound Pictures. Caroline (BG) also worked as an admissions officer at Middlesex School and Choate Rosemary Hall, an account supervisor at ISM and Fort Franklin, and a senior account executive at Hill, Holliday.

Caroline (BG) Bigelow pursued a Bachelor of Arts degree in Journalism from Saint Michael's College, which they completed from 1994 to 1998. Prior to that, they attended Newton Country Day of the Sacred Heart from 1991 to 1994.