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Miles Barry has a diverse work experience spanning various industries and roles. Miles started their career in 2014 at St. Lawrence University, where they volunteered for community-based learning for a year. In 2015, they joined the university's men's tennis team and also served as a sports commentator. Additionally, Miles was also the goalie for the St. Lawrence D1 Club Hockey Program from 2015 to 2018.

In 2019, they joined TechTarget as a Lead Gen Operations Associate, and later progressed to the role of Team Lead - Marketing Operations in August 2021. In the same year, they also worked with the Boston Bruins as part of their promotional team. Finally, from 2012 to 2021, Miles worked as a tennis instructor at Corinthian Yacht Club.

Miles Barry obtained a Bachelor's degree in Business and Communications from St. Lawrence University between 2014 and 2018.