Taylor Stockdale is the sixth head of The Webb Schools in Claremont, California. The youngest of four sons of the late Admiral James B. Stockdale, Mr. Stockdale joined The Webb Schools in 1988 as Associate Director of Admission and teacher of AP Economics. He has since served as Director of Alumni Relations, Director of Institutional Advancement and Assistant Head of Schools. Throughout his 23-year tenure at Webb, Mr. Stockdale has developed a broad range of experiences and skills – from administration to coaching, teaching and dorm parenting – and, in doing so, has acquired a track record of success in strategic planning, board development, capital fundraising and educational leadership.

Taylor and Anne Stockdale, Claire '14, Bailey '11

In his most recent role as Assistant Head of Schools, Mr. Stockdale managed the day-to-day operations of Webb including academic leadership, co-curricular activities, residential programs, and student leadership development (he was the sole administrative representative to the Honor Committee, the schools’ primary leadership and disciplinary review board). Mr. Stockdale also led the recruitment, professional development and retention efforts of a highly talented faculty and staff, and assisted with administrative tasks such as campus master plan negotiations, school budgeting, WASC re-accreditation, and strategic planning.

Mr. Stockdale was one of Webb’s longest-serving directors of institutional advancement. In this capacity, over nine years, he led two successful campaigns totaling over $40 million. During this time, Mr. Stockdale also built a professional development operation for the school, including a more effective annual fund, and a more focused effort on major gift fundraising and school marketing. Mr. Stockdale secured the first-ever seven figure commitments, including eight $1 million-plus gifts and more than 50 six-figure commitments. He also established a planned giving program and developed a special faculty initiative fund which supports faculty growth and development.

As a volunteer, Mr. Stockdale has served CASE (Council for the Advancement and Support of Education) in a number ways, including as a frequent speaker, a member of the faculty for the new advancement summer workshop, and as chair of the CASE-NAIS national conference. Mr. Stockdale also served St. Mark’s Episcopal School (Upland, CA) as a trustee as well as a trustee at South Kent School (CT), his alma mater.

Prior to his affiliation with The Webb Schools, Mr. Stockdale taught Latin, American Government and Algebra at Rumsey Hall School in Washington, CT, where he also coached football, basketball and crew and was the Director of Summer School. He graduated from Colorado College with a B.A. in History and Political Science. He received his M.A. in Economics from the University of Delaware, and a Certificate in Leadership from The Drucker School of Claremont Graduate University.

Mr. Stockdale is married to Anne Stockdale and together they have two children, Claire (VWS Class of 2014) and Bailey (WSC Class of 2011). They reside on the Webb campus.