Head of Schools Search

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Educational Directions, the consulting working with the Board of Trustees on the search effort, received more than 300 survey responses from a cross section of alumni, families, teachers, staff, students and supporters and conducted eight community meetings to gather perspectives on the selection of Head of Schools.

Comments in the surveys and focus groups said Webb’s next Head of Schools should be an inspirational innovator and visionary; an effective communicator; a strategic thinker and community builder; a person who can support external affairs, who values DEI and is focused on students; a person with rich experience open to listening to all perspectives; and someone with an authentic love for Webb.

The Board solicited input from faculty, staff, parents and alumni as well as from many Life Trustees, including Paul Reitler ’54, GP ‘13 and Susan Nelson, P ’95, ’97, former Head of Schools.


Head of Schools Taylor Stockdale will continue to lead Webb under the direction of the Board of Trustees until July 2023, when Dr. Smith will assume the executive post. During the two-year transition period, the two school leaders will continue their highly successful collaboration as Webb celebrates its centennial. In July 2023, Mr. Stockdale will shift to his new role, supporting the Webb community as Head Emeritus.

Dr. Smith has championed diversity, equity and inclusion at Webb. Her hiring practices over the last five years have created the most diverse faculty ever on the Webb campus. She also led efforts to adopt our statement of commitment to DEI values in 2018. She is a Planning Committee member of the SoCal Diversity Recruiting Fair and was the driving force behind the gender equity changes in dormitory accommodations for Vivian Webb School.

Dr. Smith will also add to Webb’s diversity on a personal level when she becomes one of the few women to serve as Head of Schools at an independent co-ed secondary boarding school.

The Selection Committee conducted an initial interview with Dr. Smith, followed by a second, more extensive discussion and a presentation/interview with the full board, Life Trustees, and a Faculty and Staff Advisory Group. She was also extensively interviewed on several occasions by our search consultants from Educational Directions.

In addition, Educational Directions engaged in one-on-one conversations with more than 15 individuals who worked with Dr. Smith, consulted with the Faculty and Staff Advisory Group and reviewed the results of the surveys and focus groups. The consultants and the Board also conducted 14 separate reference checks.

The Selection Committee began its search by assessing the potential match between the leadership skills sought and the skills, experience and vision of Dr. Smith, whose role at Webb placed her at the top of the search list. Educational Directions also gathered resumes from a diverse and representative pool of leaders that are potential applicants for 2022 headship roles to ensure Dr. Smith’s evaluation was conducted within the context of a competitive field. In all, resumes from 10 other potential applicants were examined.

The Board of Trustees formed a Selection Committee led by Board of Trustees Chair Sanjay Dholakia, WSC ’87 and Executive Committee Member Dr. Wendin Smith, VWS ‘89.

The committee retained Educational Directions, an independent school search firm with deep experience. This firm assisted with the leadership transition to Taylor Stockdale 14 years ago. The committee also worked with the Glasgow Group, which has assisted Webb with initiatives centered on Diversity, Equity and Inclusion.

The first stage of the process was to determine leadership qualities desired in the next Head of Schools. All members of the Webb community, including parents and alumni, received surveys seeking their perspectives, followed by invitations to participate in focus groups managed by our consultants. The Board also determined that it would begin its review of candidates with Associate Head of Schools Dr. Theresa Smith.


The Centennial Years will allow us to celebrate Webb’s past 100 Years, its Next 100 Years, Mr. Stockdale, and other longstanding faculty and staff members, in multiple moments and venues. Plans will be adapted appropriately for the COVID-19 environment.

More information will certainly follow, and we encourage you to engage our Development Team, Alumni Council, and other channels if you have questions or suggestions.