In early January, Head of School Tom Gilder announced his plan to retire at the end of the 2024-25 school year. This timing gives the School ample opportunity to engage in a thorough search process to identify its next Head of School. 

It is impossible to adequately express the immense impact Tom has had on the School over his 37 years as Head. While we are sad to see him go, we are also overjoyed for him as he looks forward to his well-deserved retirement. Thanks to Tom’s efforts, and that of our Board of Trustees and Administrative Team, the School is in an excellent position as we prepare for this transition. Our enrollment numbers are at an all-time high, our Capital Campaign is in full swing, and the construction of our new state-of-the-art Innovation & Arts Center is already underway. We also launched our new Strategic Plan last year which outlines the direction and guiding principles of the School for the next six years. 

A search committee of current and former trustees has already begun the nationwide process to recruit a new Head of School. We are proud to announce that we have enlisted the services of Resource Group 175 (RG175) to aid us in our search. RG175 specializes in helping independent schools recruit and identify their next leaders. The Search Committee is committed to a search process that is inclusive and transparent. We are confident that the combined efforts of the Search Committee and RG175, with the valuable input of our entire community, will help us  identify the leader best suited to build on our School’s rich history.

Search Consultants

The Board of Trustees and Head of School Search Committee are very pleased to partner with Resource Group 175 (RG175) in the effort to identify Windward’s next Head of School. Our search team includes Deborah ReedSteve Morris and John Farber, each of whom have many years of experience as heads of independent schools.

search TIMELINe

  • Announcement: January 2024
  • Position Posted: February 2024
  • Application Deadline: March 25, 2024
  • Semifinalist Interviews: April 2024
  • Finalist Visits: May 2024
  • Appointment: June 2024
  • Start Date: July 1, 2025

search committee

  • Elliot Gordon '74  - Committee Co-Chair, Current Trustee
  • Michelle Alvarez Taub - Committee Co-Chair, Current Trustee
  • Ted Fikre - Former Trustee
  • Alex Kwit - Chair of the Board of Trustees
  • Chelsea Patterson - Current Trustee, Parent Guild President
  • Colin Rose - Current Trustee, Faculty Member
  • Amy Eldon Turteltaub - Current Trustee

Frequently Asked Questions