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Tommy Riley has a diverse work experience, starting with their role as a Ranch Hand at Duckett Creek Ranch from 2007 to 2012, where they gained skills in irrigation projects, fencing, and overall ranch maintenance. In 2014, they worked as a Photographer for The Catalyst Newspaper. In 2016, they served as a Sports and Entertainment Marketing Intern at Pro Sports Marketing Ventures & Promotions. Tommy then transitioned to the United States Olympic Committee, where they worked as a Project Coordinator from 2017 to 2018. Following this, they joined The Pinnacle Companies as a Marketing Associate from 2018 to 2019. Additionally, in 2018, they co-founded Handoff, a company acquired by Encompass Technologies in 2020, where they held the role of VP of Growth. Notably, they continued their position as VP of Growth at Encompass Technologies, which they have held since 2018.

Tommy Riley has a Post Graduate Certificate in User Interface Design from BrainStation. Tommy also holds a Bachelor's Degree in Economics from Colorado College and a Bachelor of Arts in Business, Management, Marketing, and Related Support Services from the University of Sydney. Additionally, Tommy has obtained a Lifeguard certification from the American Red Cross in June 2014.