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Chester Taylor began their career in 2012 as a Supplemental Instruction Leader at RIT, where they attended introductory Computer Science courses with new students to act as a peer mentor, observing the lecture with them to follow the curriculum and then planning and leading out-of-class study sessions. Chester also attended Supplemental Instruction staff meetings to learn strategies for effective teaching, peer leadership, and basic marketing principles. In 2014, they became a Software Engineer and Co-Founder at Token.

Chester Taylor attended Rochester Institute of Technology from 2011 to 2016, graduating with a Bachelor of Science in Computer Science. Prior to that, they attended Hillsboro High School from 2007 to 2011, where they earned their High School Diploma.