Nationwide search results in appointment of experienced private school leader
The Cheshire Academy Board of Trustees on Oct. 17 announced the appointment of J. Thomas “Tom” Woelper as the next head of school of Cheshire Academy upon the recommendation of the Search Committee and the unanimous approval of the Board. The announcement was made after a comprehensive, nationwide search in partnership with Educators Collaborative. Woelper will assume the head of school role on January 1, 2025.
Woelper, most recently the founding head at New England Innovation Academy in Massachusetts, was chosen after a national search and from a large, diverse pool of applicants.
“I am pleased to announce that we have found a highly respected career educator and seasoned head of school who has both the personal and professional qualities that were mandated in our search for our next head of school. Further, he has demonstrated the vision to lead CA into its next chapter,” Board Chair Jennifer Freedman P’15 in a letter to the Cheshire Academy community.
Woelper has spent his adult life working in education predominantly in the boarding school world at such institutions as Taft, Groton, Lawrenceville, and Hotchkiss. He was a head of school at a K-9 boarding and day school in New Jersey and was the founding head of school at a cutting-edge start-up school, The New England Innovation Academy. Woelper and his wife, Heidi, also lived abroad, where he was the head of school at the American Pacific International School, Thailand.
With a prestigious educational background, Woelper graduated from the Lawrenceville School and has an AB from Princeton University, where he was a scholar athlete and played Division I lacrosse. He then went on to earn a master’s degree in history from the University of Connecticut and a master’s in educational leadership, with a focus on private school education, from Teachers College, Columbia University.
“Upon visiting Cheshire Academy, I was impressed by the campus’s warmth and unique position among private schools, as a welcoming global community focused on rigorous academics, engaging arts and athletics, and peerless college counseling,” Woelper said. “I’m excited to call Cheshire Academy home.”
Woelper succeeds Head of School Julie Anderson P’19,’23, who has been part of the Cheshire Academy community for 22 years. Anderson, will be on sabbatical until July 1, when she begins her new post as head of school at Rectory School in Pomfret, CT.
“I am excited to watch Cheshire Academy’s continued growth under Tom’s leadership, and I will always be a proud supporter of this remarkable institution,” said Anderson, who initially announced in February that she would be stepping down.
This appointment marks an exciting chapter in the history of the school. “We believe that Tom will build upon the foundation laid by Julie Anderson,” Freedman. “We are immensely grateful to Julie for her passionate leadership and care, and will be honoring her in future communications and events.”
Cheshire Academy is excited to welcome the Woelper family, including sons Alejo and Tomás, to campus, as the school continues its rich legacy and meets the future together.
For more information, please visit our Head of School Search webpage.
