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Jessica Cunningham is the chief academic officer of KIPP (Knowledge Is Power Program) DC. Previously, Cunningham founded KIPP DC's third middle school, WILL Academy, in July of 2006 and served as the school's principal for four years. Cunningham joined KIPP DC in 2003 as the sixth grade math teacher at KIPP DC's founding school, KEY Academy. She taught at KEY Academy for two years before being accepted to the KIPP Foundation's Fisher Fellowship. Prior to joining KIPP DC, Cunningham was a member of the DC Teaching Fellows' inaugural cohort, where she taught fourth grade at Garfield Elementary in Anacostia for two years. Cunningham earned a B.S. in African American History from Florida A&M University and an M.A.T in Elementary Education from American University. She is a Fellow of the fourth class of the Entrepreneurial Leaders for Public Education Fellowship and a member of the Aspen Global Leadership Network.