Taylor Stockdale has developed a broad range of experiences and skills in independent schools over the past 23 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.

Prior to being named Head of Schools at The Webb Schools, he served as Assistant Head managing the day to day operations of Webb including academic leadership, co-curricular activities, student leadership development, and residential programs. Taylor also led the recruitment, professional development and retention efforts of a highly talented faculty and staff.

Taylor previously served nine years as Webb’s Director of Institutional Advancement and led two successful campaigns totaling over $50 million. During that time, Taylor 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. Taylor also secured the school’s first-ever seven figure commitments, while establishing a planned giving program and developing 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 also served as a trustee of St. Mark’s School (Upland, CA) and of South Kent School (CT), his alma mater.