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Randall Weidberg's work experience spans several industries and includes both entrepreneurial ventures and government service. Randall co-founded Gray Digital, a human-centered digital services company focused on transforming government services through design and technology. Prior to that, they served as a Product and Digital Service Executive at the United States Digital Service, where they led teams in transforming high-impact platforms and services for the American people. Randall also worked in a similar role at the U.S. Department of Homeland Security and the U.S. Department of Veterans Affairs. Before their government service, Weidberg held leadership positions at Groupon and LivingSocial, where they led product management teams in developing consumer and merchant products. Additionally, they founded and served as Chief Product Officer at Giantnerd®, a successful social commerce website. Earlier in their career, Weidberg founded and served as CEO of the Tommaso Bicycle Company, an innovative direct-to-consumer eCommerce bicycle manufacturing retailer. Throughout their career, they have demonstrated a strong focus on customer-centric product strategies and leading cross-functional teams.

Randall Weidberg has a degree in Data Analytics from General Assembly. Randall also holds a Bachelor's Degree from St. Lawrence University. In addition, Randall has completed an Academic Enrichment Program at the University of Oxford. Randall attended Choate Rosemary Hall for their secondary education, although the exact degree or field of study is not specified.