Taylor B. Stockdale

Taylor has developed a broad range of experiences and skills in independent schools over the past 37-plus years. During this time, he has held numerous roles ranging from classroom teacher to head of school, and in doing so, he has acquired a track record of success in educational leadership, strategic planning, board development, and capital fundraising. Most notably, as Head of Schools at The Webb Schools, Taylor has implemented a Centennial Strategic Plan and Centennial Campaign. Currently the Centennial Campaign stands at nearly $200 million, the majority focused on endowment to support student financial aid and faculty enhancements (compensation, professional development and housing). 

Before becoming head, Taylor was a classroom teacher, coach, dorm head, and held other administrative positions, including Director of Institutional Advancement for nine years.  In this capacity, he led two successful campaigns totaling over $50 million; 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; secured the School’s first-ever seven-figure commitments; established a planned giving program; and developed a special faculty initiative fund which supports faculty growth and development.

As a volunteer, Taylor 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. Taylor has served as a trustee for St. Mark’s School (Upland, CA) and for South Kent School (CT), his alma mater.