Taylor B. Stockdale

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 acting 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.

In his current position as Assistant Head of The Webb Schools, Taylor manages and oversees the day to day operations of Webb including academic leadership, co-curricular activities, student leadership development, and residential programs. Taylor also leads the recruitment, professional development and retention efforts of a highly talented faculty and staff.

Prior to his current role, Taylor served as Webb’s Director of Institutional Advancement for a period of nine years, and in this capacity, led two successful campaigns totaling over $50 million. During this 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 St. Mark’s School (Upland, CA) as a trustee and currently is a trustee of South Kent School (CT), his alma mater.

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