Woelper among 100 independent school educators recognized for advancing innovation in the curriculum, AI, and school leadership
Cheshire Academy Head of School Tom Woelper is one of The 100 Independent School Innovators 2026, a select group of school leaders whose work is making learning more meaningful, more equitable, and more future-facing. Recognized by Toddle, a leading AI-powered platform for teaching and learning, Woelper was invited to join those chosen at The Summit, a December gathering for peer exchange and curated roundtables with other top national educators.
Toddle, used by 100,000+ educators worldwide, chose the winners from more than 600 applications. Woelper was recognized for his work on Cheshire Academy’s forward-thinking Strategic Plan in the Leadership & Systems Change category, which considered ways leaders reshaped the culture, governance, or structures that determine what schools prioritize, fund, and sustain.
“I’m grateful for this recognition, and I accept it on behalf of the people who did the work,” said Woelper, who has written essays about school innovation published in Independent School Magazine and EdTech Digest. “Our faculty, staff, students, families, and trustees spent over a year telling us who Cheshire Academy is and who it needs to become. The plan reflects that. What I’m proudest of is that it is already changing how we support students and how we organize our work.”
The 100 strives to recognize those who are redefining what education looks like in America today. The selection panel included some of the most respected names in education, including author award-winning author Jay McTighe, Stanford University Senior Lecturer Denise Pope, and facilitator and strategic advisor Eric Hudson.
Since arriving at Cheshire Academy in January 2025, Woelper has guided the school’s strategic planning process to answer two crucial questions: “Who are we?” and “Where are we going?” More than 250 members of the school community – students, faculty, staff, alumni, donors, trustees, families, and friends – have joined the conversation. Their thoughts, concerns, and praise led to a refreshed mission statement and then the Strategic Plan approved by the Board of Trustees in June 2026.
Read more about Cheshire Academy’s Mission Statement and Strategic Plan.
