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Rob Wentworth has a diverse work experience spanning multiple industries and roles. Rob most recently worked at Harry's, Inc. as a Senior Counsel, starting in 2020. Prior to their role at Harry's, Inc., Rob worked as a Legal Counsel at the same company from 2020 to 2023.

From 2016 to 2020, Rob was a Real Estate Associate at Simpson Thacher & Bartlett LLP. Rob also had a summer associate role at the same company in 2015.

Rob gained legal experience as a Legal Extern at the United States Attorney's Office in 2014 and as a Legal Intern at The Waterfront Commission of the New York Harbor in the same year.

Before pursuing a legal career, Rob worked as an Education Technician at the Federal Bureau of Prisons from 2012 to 2013. Rob also had teaching experience as a Graduate Instructor in English and Rhetoric/Composition at the University of South Carolina from 2008 to 2011.

Rob Wentworth earned a Bachelor's degree in English from Georgia College & State University in the span of 2003 to 2006. Following this, they pursued a Master of Fine Arts in Creative Writing at The University of South Carolina, completing their degree between 2008 and 2011. Later, Wentworth attended New York University School of Law from 2013 to 2016, where they obtained their Doctor of Law (J.D.) degree.