Head of School Search

February 15, 2021

Dear Winston Community,

It is with great excitement that I announce to you that the Board of Trustees has voted unanimously to appoint Dr. Josephine Iacuzzo Diemond as Head of School of The Winston School effective July 1, 2021, upon the retirement of Dr. Peter Lewis in June. Josephine comes to us from McLean School of Maryland, a K-12 co-educational, college preparatory school located in Potomac, Maryland, where she has been Head of Upper School since 2006.

Last fall our Search Committee, under the leadership of Trustee Leslie Lloyd (P’20) and aided by Wickenden Associates, embarked on a process to engage the community in defining and seeking the essential attributes for our next head of school. After receiving this community input, the committee reviewed numerous applications from a nationwide search and conducted interviews with seven well-qualified semi-finalists. From this group, three outstanding finalists were chosen to visit our school in January for interviews with representatives of our community, including parents, faculty, administrators, alumni and Trustees. The Search Committee carefully reviewed community feedback from these interviews and numerous outside references for each finalist. At the conclusion of this comprehensive process, the Search Committee unanimously recommended that Dr. Josephine Diemond was the right candidate to lead our school, and our Board unanimously concurred.

From the onset of the search, we sought a visionary and innovative leader who values community, embraces individuality, and celebrates diversity - espousing a personal and educational philosophy consistent with Winston’s mission and core values. We have found that in Josephine Diemond. Guided by a life-long passion for learning and strong desire to share the gift of education, Josephine brings 26 years of experience as a teacher and administrator, including 15 years at McLean working with many bright students with language-based learning differences. Josephine has a strong track record of putting student needs first while leading and growing exceptional educational programs that address the “whole child.” At McLean she led the development and expansion of a newly formed upper school, increasing programming and enrollment and helping to manage a major facilities expansion, while keeping the feel of the institution as a small, caring place.

Her dedication to student success is built on a belief that the best student experiences are built on a foundation of collaboration and community. She understands that faculty and staff provide the energy needed for students to thrive and that her support, as head of school, is essential. Similarly, she understands that parents are critical partners in the education of any student. Josephine works tirelessly at fostering positive relationships with faculty, students and parents.

The Board of Trustees was impressed by Josephine’s credentials and breadth of experience as an administrator. She earned her doctorate in Educational and Organizational Leadership from the University of Pennsylvania, a master’s degree in French Literature from New York University and a bachelor’s degree in biology from Princeton University. Throughout the process, Josephine’s colleagues offered consistent outstanding praise for her steady and reliable leadership and ability to develop a culture of trust and support with faculty, students and parents. 

We look forward to welcoming Josephine, her husband Jed, and daughter Gabriella, a current high school senior, to Winston this summer. In the meantime, we will work with Josephine and Dr. Peter Lewis to ensure her successful transition to The Winston School. During the next few months, you will hear more about Josephine as she meets and learns more about our community. We intend to host multiple opportunities for you to meet Josephine and will share details when we have them.

I am confident that under Josephine’s leadership, The Winston School will reach new heights in our mission to recognize difference and enable success.

On behalf of the Board of Trustees, please join me in welcoming Dr. Josephine Diemond to The Winston School. We believe she will be an exceptional leader for our school.


Jennie Tinkelman

President, Board of Trustees

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