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Barry Plunkett started their work experience as a Legislative Intern at Howard County Government from January 2015 to August 2016. Barry then worked as a Mathematics Tutor at the University of Pennsylvania from January 2017 to August 2017. In May 2017, they joined the University of Pennsylvania as a Research Assistant and continued in that role until July 2020. During their time at the university, they also worked as a Course Developer and Teaching Assistant for ECON 224 from May 2018 to December 2018. From January 2018 to July 2020, Barry served as a Computer Science Teaching Assistant at Penn Engineering. In 2020, they joined The D. E. Shaw Group as an Associate, where they worked until April 2022. Currently, Barry is the Co-CEO at Skip since June 2022.

Barry Plunkett holds a Bachelor of Arts degree in Economics and Computer Science from the University of Pennsylvania. However, no specific information regarding the start or end year of their education is provided.