Community Update: Head of Schools Search

March 11, 2021
Dholakia, Sanjay

Dear Members of the Webb Community,

I am writing to you today, on behalf of all of my fellow Webb Trustees, to share an update about our long-term leadership plans. As a proud member of the Class of 1987 and a member of this wonderful Board for over a decade, I am privileged to serve as our Chair. Our incredible Head of Schools, Taylor Stockdale, informed the Board last year that he intended to retire when his current contract concluded on June 30, 2023. At that time, Taylor will have served Webb for 35 years, with 13 as Head of Schools. It would not be possible in this short space to describe the positive impacts that Taylor has had on our Schools, but suffice it to say, during Taylor’s tenure at Webb, the school has flourished, becoming a thought leader among independent schools in academic, co-curricular, and student life programs. Our Alf Museum has soared to global repute, our campus footprint has doubled in size, and our faculty, staff, and senior leadership team are second to none. These notable successes have helped to drive significant growth in our endowment and even stronger demand for the Webb experience from prospective students and families around the world.


Taylor’s leadership has set the stage for us to collectively celebrate our upcoming 100-year birthday – and he will be the perfect leader to carry us through “The Centennial Years.” With that said, he has certainly earned the right to move into a new chapter in 2023. In respecting Taylor’s wishes, the Board also wants to maintain Webb’s momentum and to continue to advance the impressive programs launched during Taylor’s leadership. I am excited to report to you that Taylor has enthusiastically accepted an offer to transition his role at Webb to Head Emeritus, commencing July 1, 2023 and keeping him actively engaged until at least 2027. As Head Emeritus, he will play a lead role in completing the Centennial Campaign and in exploring strategic opportunities for Webb, while also being a powerful resource for the new Head of Schools. He will live off campus and focus his attention on securing the funding and support that will continue to fuel Webb’s future.


With Taylor’s position secured, the Trustees have turned our attention to identifying Taylor’s successor. The most important responsibility shouldered by the Board of Trustees is hiring and evaluating the Head of Schools. With that task in mind, I will co-chair a Selection Committee with fellow Executive Committee member, Wendin Smith (VWS class of 1989). This Committee will be augmented by external advisors to solicit voices, input and perspectives across our community. Notably, we have retained Amy Richards and Chris Arnold from Educational Directions, an independent school search and consulting firm based in Rhode Island, to assist the Selection Committee. Educational Directions has deep experience and expertise in our marketplace, having helped many schools like Webb. Chris assisted with the leadership transition from Susan Nelson to Taylor Stockdale 13 years ago, and Amy was the Head of School at Crystal Springs Uplands School in Hillsborough for 14 years. We also have engaged the counsel of the Glasgow Group, our Diversity, Equity & Inclusion (DEI) consultant, given our ongoing commitment to all forms of diversity, including gender, race, religion, and sexual orientation. The Board has charged the Selection Committee with conducting a thorough and complete process. This process will consider a range of options from conducting a national search to evaluating our current Associate Head of Schools, Dr. Theresa Smith – with the ultimate goal of bringing the Board the strongest candidate to support Webb’s future.

We are committed to an inclusive Head of Schools search and will seek input from the Webb community throughout. The first stage of our process will be to firmly establish the most important leadership qualities Webb will seek in order to continue thriving in the coming 10 years and beyond. As a valued member of our community, you will soon receive a survey asking you to let us know what leadership qualities you deem most important. Afterward, there will be opportunities for open discussion through Zoom meetings with Chris and Amy. You will receive timely updates from the Selection Committee on our progress, and information will be posted on the schools’ website. Please contact any member of the Selection Committee or the Educational Directions team with questions or suggestions (Click here for contact details).

The Board will begin its search by assessing the potential match between the leadership qualities we seek, and the skills, work experience, and vision of Dr. Theresa Smith. Theresa has demonstrated her strong abilities and leadership during her 10 years at Webb, particularly in the past two years as Associate Head of Schools through the pandemic. The Selection Committee’s initial evaluation of Theresa will compare her vision for Webb with the Board’s and our community’s expectations of leadership. Concurrent with our evaluation of Dr. Smith, the Committee will also identify and review a diverse pool of other leaders and potential applicants across the Boarding/Day School landscape.

Given the timing of The Centennial Years launch this fall and the competitive nature of the market, we have decided to begin our search now and complete the first phase of the Selection Committee’s evaluation of Dr. Smith by April 2021. The committee will then determine our next steps as we proceed toward July of 2023.


We will provide you with more details of the timing of the selection process in our first update in a few weeks. For now, what we know for sure is that Taylor will be the Head of Schools through June 30, 2023 and will lead us through our Centennial Years before he transitions to Head Emeritus. Our Centennial Years are a topic for another letter, but please rest assured that we have even more exciting news to announce! We are so very proud, not only of what Webb has been for these past 100 years, but also of what Webb will become in the Next 100 Years. Webb’s strength comes from the collective leadership and energy from all of you – the Webb Community. Thank you for all you do to support The Webb Schools.

I am proud to be on your team.


Sanjay Dholakia
Chair, Board of Trustee
The Webb Schools

March 11, 2021

11:06 AM PST