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Stewart Stout has a diverse work experience spanning various industries and roles. Stewart started their career as an Assistant Camp Director at the Chewonki Foundation in 2007. Stewart then worked as a Finance Assistant for John Kerry for Senate from 2007 to 2008, followed by a role as a Political Intern at Organizing for America in 2010. In 2008, they became a High School History Teacher at Teach for America, where they worked until 2011. From 2011 to 2013, Stewart served as a Marketing and School Community Manager at Kickboard. Stewart then transitioned to KIPP Massachusetts, where they held the position of Director of Student Growth and Achievement from 2013 to 2016. During the same period, in 2016, they attended Metis as a Student, focusing on data science. In 2016, Stewart joined L.L.Bean as a Senior Analyst and later moved to the role of Senior Data Scientist from 2018 to 2020. Currently, they are working at Groups Recover Together, initially serving as a Director of Analytics from 2020 to 2022, and now as the VP, Analytics and Data Products from February 2022 onwards.

Stewart Stout earned a Bachelor of Arts degree in History and Environmental Studies from Bowdoin College from 2003-2007. Prior to attending Bowdoin, Stewart attended Phillips Exeter Academy from 2002-2003 and Pingry School from 1996-2002.