Head of School Zack Lehman has decided to leave the Hill School at the end of the 2022-23 School year to take on a new challenge as the new head of school at the Loomis Chaffee School.

After serving the Hill School for 11 years, Lehman, his wife, and family dog Reuben are relocating back to New England to stay closer to family and lifelong friends. “I felt it was a good time to seek a new challenge that was closer to our family and ‘home base’ in New England,” Lehman stated in an email. 

Four-year student Rocco Bressi ’23 was shocked when he heard about Lehman’s decision, “I was a little confused because the news came out without any warning.” However, Bressi understands Lehman’s decision to get closer to his family. “I wish him the best of luck and I appreciate everything he’s done for the school,” Bressi said.  

Since the start of his run at Hill, Lehman promised the Board of Trustees a minimum of 10-year ministrations to have enough time to “make substantial progress toward the school’s ambitious goals.” After a decade, Lehman believed that he has fulfilled his role. “Hill is once again considered one of the premier boarding schools in the world … because of the progress we have made at Hill, the school is in a terrific position for a leadership transition,” Lehman said.  

As such, Lehman felt his leaving as a “win-win” situation for both his family and the school’s future development. 

Lehman decided to pursue his future career at The Loomis Chaffee School, where he has some personal connections. “I have known Loomis Chaffee ever since I was in boarding school myself, the retiring head of school was my dorm parent at Exeter, and her husband was my adviser at Dartmouth,” Lehman said.   

Having a level of comfort with the school to begin with, Lehman was attracted by the “increased complexity and challenge of leading a larger boarding school” at Loomis Chaffee.  

“Like Hill, Loomis Chaffee has fantastic academics, athletics, and arts but has struggled a bit with building a strong community feeling as their enrollment has outgrown some of their community traditions and the capacity of their meeting facilities,” Lehman said. As an active community-builder at Hill, Lehman looks forward to using his experience and enthusiasm in that area to help Loomis Chaffee regain that very strong sense of community.  

Lehman recently signed a contract extension with The Hill School; however, The Hill board of trustees is very supportive of Lehman’s decision to depart ahead of schedule and transition to Loomis Chaffee.  

5th former Yuvi Singh ’24 came to The Hill School from India this fall. As a new boarding student, Singh said that it would definitely feel different without Lehman’s presence next year. “The other day I just saw him walking Reuben. It’s weird to think that I’m just getting to know him, but he is leaving next year,” Singh said.   

Stella Mueller ’26 remembered when she came to revisit day, Lehman named out each of the new prospect students and what activities they are good at. “I felt supported when he called my name during my revisit day, no one ever did that,” Mueller said.  

3rd former Robyn Eliason ’26 thought that it’s good that Lehman felt comfortable with the environment he had created at Hill that he knows he can leave, and the school will be as good as it is with the help of other faculties. 

As for the next Head of School, the Board of Trustees hired professional executive search firm RG175, which specializes in head of school searches. At the same time, Hill has composed a search committee consisting of trustees and faculty members. Together, the search firm and the search committee will develop a position description, often known as an opportunity statement, an application process, and a candidate interview and visit schedule. Lehman wrote in an email that the board of trustees hopes to name the next head of school sometime in January or February 2023, complete a transition process through the spring, and have the next Head of School assume leadership on July 1, 2023. More information about the head of school search can be found on The Hill School website.  

Lehman said that he wishes to have the best time ever with the Hill community in his last year. He is extremely grateful to the Hill community for all of their kind words and congratulations over the last few weeks since he shared my plans. “Mrs. Lehman and I have loved our experience at Hill and remain very proud of the school in every way possible. We are looking forward to a fantastic year ahead and to creating lasting memories with our collogues and students,” Lehman concluded.