Leading Webb

Head of Schools Selection

The Webb Schools Board of Trustees has named Associate Head of Schools Dr. Theresa Smith to succeed Taylor B. Stockdale in July 2023. At that time, Mr. Stockdale will transition to Head Emeritus. Stockdale, appointed in 2010, will have served Webb for 35 years, including 13 as Head of Schools. He is the sixth Head of Schools in Webb’s 99-year history.

Read more about the Head of Schools

Hooper Community Center Front Entrance school name etched in stone

Hearing Your Views

A Diversity of Perspectives

The Webb Schools Board of Trustees reviewed input from across our community to inform our Head of Schools selection process, beginning with a comprehensive survey and interviews with virtual focus groups. Our Board believes deeply in the power of assessing the Webb Community’s collective inputs to assist in the selection of the next Head of Schools. We thank our community for providing invaluable input during the search and selection process.


Search Timeline

  • Week of March 8, 2021: Internal announcements and Community notification. Sourcing of external, diverse pool of candidates. First interview with Associate Head of Schools, Dr. Theresa Smith
  • Week of March 15, 2021: Community Survey released, soliciting leadership qualities feedback. Interviews of Trustees and Administration.
  • Week of March 22, 2021: Zoom focus group meetings and Community engagement, along with interviews and background/reference checks.
  • Week of March 29, 2021: Focus group meetings continue. Dr. Smith’s application provided to Selection Committee.
  • Week of April 5, 2021: Dr. Smith interviews with Selection Committee. Written assessments of Dr. Smith and comparisons to initial external candidates completed by Educational Directions, with recommendations and final report.
  • Week of April 12, 2021: Full Board of Trustees Q&A with Dr. Smith. Selection Committee convenes to deliberate and make initial recommendation to the full Board.
  • Week of April 19, 2021: Final deliberations and decision.
  • Week of May 17, 2021: Communication of next steps to Webb Community.


Questions or Comments?

Contact our Board of Trustees Selection Committee or our consultants with Educational Directions with any questions or comments:

Selection Committee

Sanjay Dholakia
Wendin Smith ‘89
David Loo ’79
Christina Mercer McGinley ’84
Miles Rosedale ’69
Roger Millar ’61
Rahmi Mowjood ‘90
Blake Brown ’68
Denis Yip
Larry Ashton ’70
Jenna Gambaro ‘95
Deval Dvivedi ’00

Educational Directions

Chris Arnold
Amy Richards

Head of schools Search

Frequently Asked

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.


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 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 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 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.


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.

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.

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.

Head of Schools Search

Recent Announcement

Dholakia, Sanjay

Mar 11, 2021

Community Update: Head of Schools Search

May 17, 2021

Board of Trustees Selects Dr. Theresa Smith as Head of Schools Starting July 2023