Tom Gilder, Head of School at Windward

"Windward’s greatest strengths are its talented, accessible teachers and its nurturing community that creates a dynamic learning experience for our students. Our university partnerships and innovative programs, which are drawing national attention, enable our students to reach their full potential and prepare them for the new opportunities and challenges of our rapidly changing world."

-Tom Gilder

Vision of the Head of School

Tom Gilder is an accomplished leader and visionary whose more than 30 years as Head of School at Windward have been characterized by academic innovation and a talent for identifying and seizing opportunities.   
From establishing innovative programs and strategic university partnerships to supporting talented and diverse faculty and students, Tom has transformed Windward School into one of the premier independent schools in California. Windward has experienced impressive growth during Tom’s tenure, and he remains steadfastly committed to the founding values of Windward: "a dynamic education and a nurturing community."   
When Tom became Head in 1987, Windward’s 9.5 acre campus consisted of one academic building with small classrooms comparable in size to today’s offices. He understood that excellent facilities beget excellent programs, so, in partnership with the Board of Trustees, he created Windward’s Campus Master Plan. Through Tom’s leadership and the generous philanthropic support of the Windward community, Windward has completed two Capital Campaigns to create the amazing campus enjoyed today.   
During Tom's tenure, diversity at Windward has flourished. Today, 30% of the student body are students of color, compared with 1.5% in 1982. Tom recognized that a strong Financial Aid Program is the cornerstone of a diverse community and made growing the $10,000 budget a priority. In 2022-23, Windward awarded $3.2 million in financial aid. One financial aid beneficiary, now in medical school, described her Windward education as "the most precious gift anyone could have given me."   
Tom’s leadership and experience extend beyond Windward to advocacy of the broader independent school community through professional affiliations. He served as President of the California Association of Independent Schools (CAIS) and was previously the Chair of the Secondary Board of Standards for CAIS. He also served on the Steering Committee of Los Angeles School Heads (LASH) and has served on the boards of trustees for Village School and Wildwood School. Tom frequently speaks at educational conferences.   
Tom, who has spent his entire career in education, graduated from the University of California, Santa Barbara, with a B.A. in political science and earned his master’s degree in educational administration from Pepperdine University. Tom and his wife, Lori, are proud parents of two Windward alumni: Jeffrey ’08 and Jenna ’11. Jeffrey graduated from the University of California, Santa Barbara with a bachelor's degree in psychology and a master's degree in Education; he currently serves as Windward's Director of Alumni Engagement.  Jenna earned a Ph.D in Psychology from Claremont Graduate University and now serves as the Clinical Director at the May Center for Autism and Developmental Disabilities in Boston, Mass.