Leadership

Leading Women

The Winsor School has long benefited from strong, stable leadership. There have been just eight heads of school since Winsor’s founding in 1886. The trustees serve as the governing body of the school. The Winsor Corporation, part of the school’s governance structure, approves nominations to that board. Its ranks include many of the school’s most ardent and loyal supporters and ambassadors.

Meredith Legg, head of school

Winsor’s Head of School

Meredith Legg

Head of School and O’Donnell Family Chair

In describing her perspective on leadership, she reflected, “School leadership is a complex, fulfilling, and deeply human endeavor—an art and practice that requires constant attention and crafting."

Winsor's Historic Leadership

1886–1922: Mary Pickard Winsor
1922–1939: Katherine Lord
1939–1951: Frances Dorwin Dugan
1951–1963: Valeria Addams Knapp
1963–1988: Virginia Wing
1988–2004: Carolyn McClintock Peter
2004–2016: Rachel Friis Stettler
2016–2025: Sarah Pelmas
2025–present: Meredith Legg

Virginia Wang

Miss Virginia Wing, Winsor's director from 1963 to 1988

“I am honored and deeply humbled by the opportunity to serve the Winsor community as the ninth head of school. Winsor students are ambitious, thoughtful, and curious; I am excited to be a part of the educational environment at Winsor that shapes how students walk through the world with confidence and purpose.”

Meredith Legg

Administrative Council

Julian Braxton  is a board/advisory member at The Winsor School

Julian Braxton

Director of Community and Inclusion
Meet Julian
Janelle Browning  is a board/advisory member at The Winsor School

Janelle Browning

Director of Strategic Communications
Meet Janelle
Kate Casper  is a board/advisory member at The Winsor School

Kate Caspar

Associate Head of School
Meet Kate
Karen Geromini  is a board/advisory member at The Winsor School

Karen Geromini

Chief Operating Officer
Meet Karen
Sherren Granese  is a board/advisory member at The Winsor School

Sherren Granese

Director of Athletics
Meet Sherren
Denise Labieniec  is a board/advisory member at The Winsor School

Denise Labieniec

Institutional Researcher
Meet Denise
Erika Mc Mahon  is a board/advisory member at The Winsor School

Erika McMahon

Chief Advancement Officer
Meet Erika
Audra McFarland  is a board/advisory member at The Winsor School

Audra McFarland

Director of Admission and Financial Aid
Meet Audra
Sharon Jones Phinney is an African American woman wearing a gray

Sharon Jones Phinney

Head of Lower School
Meet Sharon
Kimberly Ramos  is a board/advisory member at The Winsor School

Kimberly Ramos

Head of Upper School
Meet Kimberly
Marcus Young is an African American man wearing a gray suit jacket and pink shirt

Marcus Young

Director of Technology
Meet Marcus

Board of Trustees