The Search for Winsor’s Next Head of School

July 17, 2024

Dear Winsor community,

With the news of Sarah Pelmas’s departure, the Winsor Board of Trustees is actively moving toward the launch of a national search for the new head of school who will lead Winsor into our next phase. We are well positioned for this search, and will be guided by Winsor’s culture, values, strengths, and traditions, as well as the entrepreneurial spirit that serves the school so well. We are committed to excellence in this search and will provide updates to the community as it develops.

We have retained Carney, Sandoe & Associates (CS&A) as our search firm. CS&A is an internationally recognized education search and consulting firm with extensive knowledge of independent schools and over 45 years of experience successfully guiding schools through searches for exceptional heads of school, senior administrators, and faculty. Marsha Little, Susanna Jones and President Devereaux McClatchey—our consultants at CS&A—have outstanding credentials. We are excited to partner with them.

Our priority in this search will be to find the very best person to lead Winsor down the important road ahead. We aim to identify a new head of school for the 2025–26 school year, but there is a great deal of work to be done in this process, and we will follow best practices and take the time necessary to find the top candidates for Winsor. In the event that the process requires an interim head of school for the 2025–26 school year, we have several excellent candidates to consider.

The most important responsibility of any governing board is to select the right person to lead the institution, and I want to assure you this is the highest priority for me personally, and for all of our trustees. The search will focus on both the continuity of Winsor’s values and the preeminent qualities of leadership. We will seek a new head of school to build on the achievements of the past 138 years while encouraging us to evolve, always bettering ourselves. This is an opportunity for our community to identify an outstanding new head of school for Winsor, and we are confident we will find an exceptional and impactful leader.

Our conversations and reflections throughout the search process will be directed by the mission and character of this exceptional school. Guiding us will be our shared commitment to a diverse, vibrant community that values intellectual curiosity, authentic engagement, and personal integrity; our shared mission of preparing young women to pursue their aspirations and contribute to the world; and our shared expectation that our students apply their Winsor educations and values in a world that needs them.

We have assembled a deeply committed team to serve as our search committee:

• Larry Cheng P’23, ’25, ’28, Vice President of the Winsor Corporation, Co-Chair of the Search Committee
• Lori Whelan P’23, ’25, Treasurer of the Winsor Corporation, Co-Chair of the Search Committee
• Julian Braxton, Director of Community and Inclusion and Bezan Chair for Community and Inclusion, 25 years of service to Winsor
• David Griffin, Dean of the Class of 2026, English Faculty, Fall 2023 Interim Upper School Head, 10 years of service to Winsor
• David Humphrey P’28, ’31, Current Trustee
• Marlyn McGrath ’66, P’96, ’03, Former President of the Winsor Corporation
• Suzanne Ranere Norris ’94, Current Trustee
• Allison Kaneb Pellegrino ’89, P’21, ’22, President of the Winsor Corporation
• Emily Lubin Woods ’91, P’26, Current Trustee

The search committee intends for this process to be inclusive and to reflect our community well. We will seek input and perspectives from various members of our community to ensure we have a thorough understanding of our needs as we aim to recruit and interview the most talented leaders in the country. You can expect periodic communications about the status of the search. The co-chairs of the search committee and I look forward to keeping you updated.

As we activate this search, we remain fully committed to the Winsor Leads Campaign. Already, the success of this historic campaign is an undeniable signal of the powerful support of our multigenerational Winsor community and our shared belief in the importance of Winsor as a distinguished leader in girls’ education. And as always, we remain fiercely focused on upholding the mission of the Winsor School and maintaining the school’s high academic, athletic, and personal standards for every member of our community. Thank you for your partnership during this pivotal moment for Winsor.

While our world is continually changing, Winsor remains grounded in our mission and heritage. We are eager to continue our work on behalf of Winsor in the coming academic year, and we look forward to beginning Winsor’s next chapter with all of you.

Warmly,

Allison Kaneb Pellegrino ’89, P’21, ’22
Chair of the Winsor School Board of Trustees

July 16, 2024

Dear Winsor community,

As a school community, we understand the range of feelings we all may experience when saying goodbye, especially after so recently seeing our newest class of Winsor graduates off into the world. We know that even in the most celebratory times, goodbyes are never easy.

I write to you today with the news that Sarah Pelmas has informed the Winsor Board of Trustees that her ninth year as Winsor’s head of school will be her last. While we are saddened by her departure, we are grateful for her effective leadership, selfless dedication to the education of Winsor’s students, and her work positioning the school for success in our next chapter. Sharing her decision with us now gives us the opportunity to plan for one more highly rewarding year together. I know you will all join me in thanking Sarah for her commitment to Winsor.

Sarah’s work at Winsor has been deep and wide-ranging. When she arrived, we were just finishing the largest fundraising initiative in the school’s history, and it was imperative that our head of school focus on utilizing the incredible new Lubin-O’Donnell Center and reimagining the student experience at Winsor.

Sarah nurtured the creation, development, and execution of innovative curriculum updates and a new school schedule while simultaneously shepherding us through a global pandemic. Her leadership during COVID is an excellent case study in effective management, and we are all the beneficiaries of her commitment, diligence, and disciplined leadership during a complex and volatile crisis. None of us could have known what we—and the world—would be asking of Sarah when she arrived at Pilgrim Road in July of 2016.

Sarah has presided over an exciting but challenging time at Winsor that has resulted in consistently strong applicant pools and enrollment and the very best academic, athletic, and collegiate outcomes, but most of all, she leaves what I believe to be the strongest administrative team and faculty in place to support our next head of school to lead Winsor. Through Sarah’s strong leadership, we will enter our next chapter with stability, energy, and enthusiasm for girls’ education and this storied institution.

Tomorrow I will share with you the detailed plans for our search for Winsor’s next head of school. Until then, on behalf of the Winsor Board of Trustees, I want to sincerely thank Sarah for her service to and immeasurable impact on Winsor. I know you will all join me as we celebrate her Winsor legacy throughout the coming year.

Warmly,

Allison Kaneb Pellegrino ’89, P’21, ’22
President of the Winsor Corporation

July 16, 2024

Dear Winsor community,

After much deliberation, and many bittersweet moments, I have decided that the 2024–25 school year will be my last year at Winsor. I don’t imagine there would ever be a good moment to leave Winsor, a school I love deeply, but I believe that this is the right moment for me to take a pause, and to pursue other educational opportunities. The past eight years have shown me just how much can be accomplished in a community whose values are clear, whose love for one another supersedes everything, and whose commitment to constant growth makes us just that much better each year. I am so grateful to everyone: the Winsor Board of Trustees for their commitment; the faculty and staff for their unwavering excellence and dedication; the alumnae for their loyalty and love for one another and the school; the parents for their incredible partnership through good times and challenging ones; and above all, the students, whose curiosity, energy, and delight in one another and in their education has been the greatest gift of my career.

Together, we have accomplished so much. We have built a more open and inclusive school culture—including the establishment of the Bezan Chair for Community and Inclusion; reimagined reunion weekend and introduced stronger programming for alums; increased faculty and staff compensation to ensure that it is competitive nationally; significantly increased financial aid for students and adopted a new system to identify need more broadly; expanded student leadership throughout the school; deepened partnership with families and developed a more robust Parents’ Association; increased opportunities for students through clubs, athletics, and the arts; recreated the “house” system with Panthers and Jaguars; redesigned our admission outreach, process, and experience; and created a Wellness Department with thoughtful support for student health throughout the school. We not only survived COVID but found ways to grow and improve through that time. We are engaged in a comprehensive curriculum review to ensure that Winsor’s academic program is second to none. We have upgraded all elements of the campus, and have a robust campus master plan in place that will prioritize state-of-the-art labs. We have improved much of the school’s infrastructure and have strengthened the school’s already strong financial position. We have launched the most ambitious campaign in Winsor’s history, and have tremendous momentum in our work to support students and faculty. All these accomplishments have required all of us, together. I am so honored to have stewarded this remarkable school through this time, and helped ensure that Winsor continues to thrive.

Looking ahead, Winsor has important and rewarding work to do. The Winsor Leads Campaign will continue on its record-breaking path, the curriculum review will yield exciting student-centered changes that we will roll out over the next several years, and we will continue to connect the Winsor community—students, alums, parents, past parents, friends, and faculty and staff—through events, programs, and activities that help us come together in shared support for one another and our amazing students.

In the upcoming year, my administrative team and I will work closely together to ensure a smooth transition to the new leadership of the school. Winsor has always been blessed with strong leaders and seamless transitions, and this time will be no different. As I reflect on my time, I have been blessed to spend these past eight years with you all, and I look forward to a productive and fulfilling next school year. It has been a gift to lead this school, to watch our wonderful students learn and grow up together, and to support the extraordinary experience that is a Winsor education. I could not be more grateful—from the bottom of my heart, I thank you all.

Warmly,

Sarah Pelmas
Head of School and O'Donnell Family Chair