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Claire Cunningham has a long history of work experience. Claire began their career in 2002 as the Owner/Manager of NotSo Hostel, a youth hostel in Charleston, SC. In 2005, they co-founded BiblioBazaar, LLC, a publishing company specializing in making hard-to-find public domain books available through print-on-demand technology. In 2009, they founded Celedu. In 2010, they began working at CleanEdison as the Chief Marketing Officer and Director of Product Development, and in 2014 CleanEdison was acquired by Kaplan. In 2012, they founded Lessonface, a company that connects curious students to great teachers for live music & arts lessons.

Claire Cunningham attended the College of Charleston from 1997 to 2001, where they earned a BA in History. Claire then attended both the MIT Sloan School of Management and the Massachusetts Institute of Technology from 2007 to 2009, where they earned an MBA.