Taylor Stockdale has developed a broad range of experiences and skills in independent schools over the past 25-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. Currently Head of Schools at The Webb Schools, Taylor’s career has included classroom teaching (Economics and History), managing day to day operations including academic leadership, co-curricular activities, student leadership development, and residential programs. Taylor has also lead the recruitment, professional development and retention efforts of a highly talented Webb faculty and staff.
He also served for nine years as Webb’s Director of Institutional Advancement. In that 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.