Cheshire Academy Head of School Named One of Toddle’s 100 Independent School Innovators

Tom Woelper recognized for leadership in strategic planning and schoolwide change

CHESHIRE, CT, UNITED STATES, October 23, 2026 /EINPresswire.com/ — Cheshire Academy Head of School Tom Woelper has been named one of Toddle’s 2026 List of The 100 Independent School Innovators, a national recognition honoring educators and school leaders advancing meaningful change in education. Woelper was selected in the Leadership & Systems Change category for his work guiding Cheshire Academy’s strategic planning process. Toddle, an AI-powered teaching and learning platform used by more than 100,000 educators worldwide, selected the honorees from more than 600 applications. The 100 recognizes leaders whose work is reshaping how schools approach 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. “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.”

Since joining Cheshire Academy in January 2025, Woelper has led a strategic planning process centered on two crucial questions: “Who are we?” and “Where are we going?” More than 250 members of the school community—including students, faculty, staff, alumni, donors, trustees, families, and friends—contributed their perspectives. Their input informed a refreshed mission statement and a Strategic Plan approved by the Board of Trustees in June 2026.

The recognition highlights Woelper’s approach to building a shared vision for the school and translating community input into priorities for its future. One example is Cheshire Academy’s new Purposeful Action Framework, which puts the school’s long-held motto, “ich dien,” or “I serve,” into practice by making service a more intentional, integrated part of school life. The initiative began with faculty and staff working in small groups on service projects across campus, in Cheshire, and throughout the greater New Haven area during opening meetings.

The Toddle selection panel included education leaders and authors Jay McTighe, an award-winning author; Denise Pope, a senior lecturer at Stanford University; and Eric Hudson, a facilitator and strategic advisor.

Learn more about Cheshire Academy’s Mission Statement and Strategic Plan and The 100 Independent School Innovators.

About Cheshire Academy
Founded in 1794, Cheshire Academy is a coeducational college-preparatory boarding and day school for grades 9-12 and postgraduate. With 370 students from 13 states and 18 countries, Cheshire Academy takes a tailored approach, providing students with a wide variety of academic and extracurricular offerings that are optimal to their individual needs, strengths, and interests. Located in Cheshire, Connecticut, the 104-acre campus rests in a quintessential and safe New England community conveniently located between New York and Boston. Cheshire Academy’s supportive, one-to-one college counseling program begins early on, resulting in commitments to some of the country’s most competitive colleges and universities. With a wide range of programming, Cheshire Academy offers the world-renowned International Baccalaureate, Roxbury Center for Learning & Leadership, Global Citizenship Diploma Distinction. The Academy is home to 17 athletic teams, with over 30% of student-athletes in the Class of 2025 going on to play at the collegiate level. Learn more at cheshireacademy.org.

Sarah LeBlond
Cheshire Academy
sarah.leblond@cheshireacademy.org
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