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Ken Sterry has a diverse work experience, beginning with a role as an Engineering Assistant at Pawling Corporation in 2002. In 2009, they were an Assistant Language Teacher at the Ibaraki Board of Education, where they taught English to Japanese high school students. From 2011 to 2013, they were a Karate Instructor at Ryu Renshi Dan Kanku Dojo. During this same time period, they were also an Associate Game Designer, Customer Support Associate Game Lead, Senior Customer Support Specialist, and Customer Support Specialist at KIXEYE. From 2013 to 2016, they worked at HarperCollins Publishers as an Administrative Assistant. Finally, from 2016 to 2022, they worked at Skillz Inc. in various roles, including Senior Strategy Analyst, Manager of Event Operations, Manager of VIP Operations, and VIP Relationship Manager. In 2022, they began working at Tether Studios as a Game Data Analyst.

Ken Sterry earned their Associate's degree in Liberal Arts and Sciences, Honors Advisement Track from Dutchess Community College in 2007. Ken then attended SUNY New Paltz, where they completed a Bachelor of the Arts in English in 2009.