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myWindward

The Search for Windward's Next Leader

Search Statement

Looking Ahead

THIS SECTION WILL FEATURE WELCOME FROM SEARCH COMMITTEE CHAIR

Learn more about the position
girl writing on paper with a pencil

Meet the Search Committee

Windward Search Committee Board Members

Denis O’Leary III ’06

Search Committee Chair, Trustee, Windward Alumnus

Maria Reed

Board President, Alumni Parent

Beth Demba

Trustee, Current Parent

Petra Miebach

Trustee, Alumni Parent

Josh Rosen

Trustee, Alumni Parent

Reed Switzer ’19

Trustee, Windward Alumnus

Windward Search Committee School Members

Lori Squillante

Assistant Campus Head, Westchester Lower School, Alumni Parent

Diane Kissner

Director of Outplacement

Nicole Berkowitz

Coordinator of Language, Speech-Language Pathologist, Manhattan Middle School

Alex Frelinghuysen

Mentor Teacher

Search Communications

Dear Windward Community,

I am writing to share an important update on our search for Windward’s next leader. Following a thorough process in which we considered several leading search firms, the search committee has selected Russell Reynolds Associates as our search partner.

Russell Reynolds stood out for the strength of its team, its experience across education, nonprofit, and corporate leadership searches, and its understanding of Windward’s mission and needs. We also valued the firm’s thoughtful strategy for engaging the Windward community and its commitment to building a broad and diverse pool of candidates. We believe Russell Reynolds will be a strong partner in this important work. You can learn more about the firm here, and click these links to meet consultants Anne Coyle and Claire Godwin who will be leading the process at Russell Reynolds.

Russell Reynolds will visit each of our campuses and hold listening sessions across the Windward community. These conversations will give our faculty and staff, families, alumni, and supporters an opportunity to share what they value most about Windward, their perspectives on its future, and the qualities they believe are most important in our next leader. You will receive further information regarding these visits soon.

As we shared when we announced the Search Committee, we have a clear mandate: to identify a leader who is committed to Windward’s mission, can build on the School’s nearly 100-year record of educational impact, and can set its strategic direction in collaboration with the board for the years ahead.

We will continue to share updates on the search timeline and key milestones as the process moves forward. You can find these on a dedicated page on the School’s website in the coming days.

If you have questions about the search, please contact the Search Committee at SearchCommittee@thewindwardschool.org. If you would like to nominate a candidate for Windward’s next leader, please contact Russell Reynolds at windward@russellreynolds.com.

Throughout this process, Windward’s mission and the impact we have on our students will remain at the center of our work. We understand the importance of this responsibility and are grateful for the community’s engagement and support as we take this next step together.

Sincerely,

Denis O’Leary, III ’06
Search Committee Chair

Dear Windward Community,

I am writing to share an update on the search committee for Windward’s next leader. We are pleased to welcome Alex Frelinghuysen as the newest member of the Committee.

Alex brings an important additional perspective to our work as a current member of the Windward faculty. A mentor teacher who has been at Windward for nearly 15 years, Alex was the recipient of the 2021 Isabel Greenbaum Stone Master Teacher Award in recognition of her work with students and commitment to the Windward community. Her experience in the classroom and understanding of Windward’s educational approach will be valuable as the Committee continues its work.

With Alex’s addition, the search committee includes:

Windward Search Committee Board Members

Denis O’Leary, III, Search Committee Chair, Trustee, Windward alumnus
Maria Reed, Board President, alumni parent
Beth Demba, Trustee, current parent
Petra Miebach, Trustee, alumni parent
Josh Rosen, Trustee, alumni parent
Reed Switzer, Trustee, Windward alumnus

Windward Search Committee School Members

Lori Squillante, Assistant Campus Head, Westchester Lower School, alumni parent (25-year tenure at Windward)
Diane Kissner, Director of Outplacement (30-year tenure at Windward)
Nicole Berkowitz, Coordinator of Language, Speech-Language Pathologist, Manhattan Middle School (10-year tenure at Windward)
Alex Frelinghuysen, Mentor Teacher (nearly 15-year tenure at Windward)

Please join us in welcoming Alex to the Search Committee.

Sincerely,

Denis O’Leary, III ’06

Dear Windward Community,

Selecting Windward’s next head of school is one of the board of trustees’ most important responsibilities. Today, we are writing as board president and search committee chair to announce the Search Committee and outline the process ahead.

The board has appointed a search committee to lead this work and make a recommendation to the full board of trustees. We have a clear mandate: identify a leader who is committed to Windward’s mission, can build on the School’s nearly 100-year record of educational impact, and set the strategic direction in collaboration with the board for the years ahead. In alignment with Windward’s core values, the search committee is dedicated to cultivating a diverse pool of leadership candidates.

Windward enters this process with strong leadership in place. Interim Head of School Alexis Pochna has served Windward for more than 20 years and has had a significant impact on the School and its community. She has the full confidence of the board. We are grateful for her leadership and for the work of Windward’s faculty and staff each day.

The Search Committee includes trustees and school leaders with a deep understanding of Windward and its community:
Denis O’Leary, III, search committee chair, trustee, Windward alumnus
Maria Reed, board president, alumni parent
Beth Demba, trustee, current parent
Petra Miebach, trustee, alumni parent
Josh Rosen, trustee, current parent
Reed Switzer, trustee, Windward alumnus
Lori Squillante, assistant campus head, Westchester Lower School, alumni parent (25-year tenure at Windward)
Diane Kissner, director of outplacement (30-year tenure at Windward)
Nicole Berkowitz, coordinator of language, speech-language pathologist, Manhattan Middle School (10-year tenure at Windward)

We will share additional details in the coming weeks, including the searchtimeline, our search partner, and how we will seek input from across the Windward community.

Windward’s mission and its impact on students will remain at the center of this process. We understand the importance of this responsibility and look forward to keeping the community informed as the search progresses.

Sincerely,
Maria Reed
Board President

Denis O’Leary, III ’06
Search Committee Chair

Contact the Search Committee

If you have questions about the search, please contact the Search Committee. If you would like to nominate a candidate for Windward's next Head of School, please contact Russell Reynolds.

Search Committee
SearchCommittee@thewindwardschool.org

Russell Reynolds
windward@russellreynolds.com

History

The Windward School officially celebrates its centennial anniversary in 2026.

Mission

Every decision at Windward is mission-driven, anchored by a deep commitment to the students we serve.

Core Values

At the heart of Windward's approach to education are four core values