Thomas Flemma

Tom is the head of school at North Shore Country Day School in Winnetka, Illinois. An historian by training, he has worked in independent schools his entire career, after earning his B.A. at Stanford and M.A. and Ph.D. at the University of Virginia. For 17 years, Tom worked at the Hotchkiss School, where he taught American history, coached, lived in the dormitory, and served in a number of administrative positions, including associate head of school and dean of faculty.

In 2016, Tom moved to Winnetka to become the ninth head of school at NSCDS, a JK-12 school just north of Chicago. In his time there, Tom has led the celebration of the School’s centennial, launched a capital campaign, and navigated COVID-19, along with the usual myriad of head of school duties.