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The Webb School Names Historic 14th Head of School
Dave Trout


The Webb School is pleased to announce Polly A. Parker, Ph.D., as its next Head of School - the 14th such appointment in The Webb School's 154-year history, and the first female to hold this office. The Search Committee unanimously recommended Dr. Parker to the Board of Trustees, citing her extensive experience, collaborative vision, and proven leadership in independent and boarding school education. The Board also voted unanimously to appoint Dr. Parker, who will officially take on her role in Summer 2025.
 

“Webb is in an exciting season filled with opportunities and challenges as we chart the next chapter in our 154-year history,” shared Dr. Chase Spurlock, Co-Chair of the Search Committee. “The Search Committee and Board of Trustees recognize the importance of finding a new Head of School who can build upon Webb's accomplishments and growth over the last several years, honor what makes Webb unique, and confidently lead the school into the future. We believe we have found that person in Dr. Polly Parker. We look forward to the vision, enthusiasm, and expertise she will bring as she leads this historic institution.” 
 

“The Webb Board of Trustees enthusiastically welcomes Dr. Parker as our next Head of School,” shared Farrar Vaughan, Chair of the Board of Trustees. “She has the experience, leadership, community-building, and problem-solving skills needed to lead Webb in the coming years.”
 

Dr. Parker’s distinguished career includes strengthening boarding schools, fostering inclusive communities, and promoting student-centered programming. Her leadership philosophy is rooted in collaboration, transparency, and continuous improvement. With extensive experience in financial management, fundraising, and strategic planning, she is well-equipped to address Webb’s current needs while honoring its traditions and values as the Webb community looks ahead to the future.
 

“The Webb School has a storied legacy of academic excellence and character-based education,” shared Head of School Elect Dr. Parker. “I am deeply honored to become part of Webb’s rich history and to serve as its first female Head of School. As I take on the privilege of leading this institution, I am deeply committed to embracing, cherishing, and nurturing the vibrant spirit that defines Webb.”
 

Earlier this month, Dr. Parker visited campus as a final candidate and interacted with faculty, staff, students, parents, alumni, and community members. The Search Committee incorporated these groups' surveys and comments into the decision-making process.
 

One survey respondent described her as "straightforward, honest, professional, and experienced,” while another highlighted her dedication to being part of the local community. Another Webb community member shared, “She demonstrated her willingness to cultivate personal relationships with students, listen to feedback, and use that input to create actionable strategies.”
 

Current Head of School, Ken Cheeseman, looks forward to working with Dr. Parker in the coming months. “My hope has always been that Webb would find a leader to help this amazing school thrive in the years to come,” shared Cheeseman. “We are truly blessed to have someone with this caliber of experience, character, business savvy, and leadership ability ready to take the reins. I have been thoroughly impressed with Dr. Parker in all my interactions with her, and I am truly excited for this next chapter in her life and the next chapter in Webb’s history.”
 

Mr. Cheeseman and Dr. Parker will collaborate throughout much of the first half of 2025 to ensure continuity in the transfer of leadership. In the coming months, we will share more from and about Dr. Parker, including a feature story in the Winter edition of Webb Magazine.