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Rebekah Monson has diverse work experience spanning various roles in media, communications, and technology. Rebekah co-founded Letterhead in 2021 where they serve as the Cofounder and COO. Prior to that, they co-founded WhereBy.Us in 2014, managing editorial and product for the Miami-based startup. Rebekah has also worked at the University of Miami as a Communications Manager, College of Arts & Sciences Editor, and Teaching Assistant from 2011 to 2014. Before that, Monson worked at the South Florida Sun Sentinel in roles such as Boca Raton Reporter, Your Money Community Manager, Sports Design Director, Business Design Director, and News Projects/1A Designer. Rebekah started their career as a Designer at The Spokesman-Review in 2003 and also had internships at The Oregonian in the same year and The Statesman-Journal in 2002. Monson was a VJ College Fellow at the Poynter Institute in 2003.

Rebekah Monson pursued their higher education by completing a Bachelor of Arts (BA) degree in Journalism, Mass Communication, and Graphic Design from Louisiana State University. Rebekah attended the university from 1999 to 2003. Years later, from 2013 to 2016, Rebekah enrolled in the University of Miami, where they earned a Master of Fine Arts (MFA) degree in Interactive Media.