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Rebekah Monson has a diverse work experience spanning different industries and roles.

Rebekah is currently the Cofounder and COO of Letterhead, a company they joined in 2021.

Prior to this, Rebekah founded WhereBy.Us in 2014, where they managed editorial and product for a Miami-based startup that produced media and events targeting millennials in emerging cities. Their role involved a combination of UX, business, journalism, and technology.

From 2011 to 2014, Rebekah worked at the University of Miami, where they held multiple positions. Rebekah served as the Communications Manager from October 2013 to September 2014, the College of Arts & Sciences Editor from November 2011 to October 2013, and a Teaching Assistant from January 2013 to May 2013.

Before their time at the University of Miami, Rebekah worked at the South Florida Sun Sentinel starting from 2005. Their roles at the Sun Sentinel included Boca Raton Reporter, Your Money Community Manager, Sports Design Director, Business Design Director, and News Projects/1A Designer.

Rebekah also gained experience as a Designer at The Spokesman-Review in 2003 and as a VJ College Fellow at the Poynter Institute from June 2003 to July 2003. Rebekah started their career as an Intern at The Oregonian in 2003 and The Statesman-Journal from May 2002 to August 2002.

Rebekah Monson holds a Master of Fine Arts (MFA) degree in Interactive Media, which they earned from the University of Miami between 2013 and 2016. Prior to their graduate studies, Rebekah obtained a Bachelor of Arts (BA) degree in Journalism, Mass Communication, and Graphic Design from Louisiana State University, where they attended from 1999 to 2003.