Guest
Tom Woelper
Head of school at Cheshire Academy in Connecticut. Tom brings more than 30 years of experience in independent education. He served as the founding head of New England Innovation Academy, and his career includes work in Gronton, Taft, and Hotchkiss. He holds a bachelor's degree from Princeton University and a master's degree in history from the University of Connecticut. He also earned a master's in educational leadership from Teachers College, Columbia University with a focus on private school education. In his November 2025 guest column for EdTech Digest, The Case for Private High School in a Tech-Driven World, Tom explores how teachers can help students develop the judgment and independence they need in a world shaped by AI.