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Mr. Stockdale will continue to lead Webb as Head of Schools until his current contract concludes on June 30, 2023. At that time, he will retire, having served Webb for 35 years, including 13 as Head of Schools.

No. The current leadership structure will remain as it is today, carrying us through our Centennial Years.

The plan has two primary parts – 1) Mr. Stockdale’s continuing role with Webb, and 2) Transitioning to a new Head of Schools.

  1. Mr. Stockdale 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.
  2. The Board has engaged an external consultancy, Educational Directions, to support the Board Selection Committee with conducting a thorough and complete process to firmly establish the most important leadership qualities Webb will seek in its next Head of Schools and make a final recommendation on a new Head. 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 goal of bringing to the Board the strongest candidate to support Webb’s future.

During the past decade, Webb has:

  • Become a leader among independent schools in academic, co-curricular, and student life programs.
  • Doubled the size of the campus by acquiring adjacent hillside properties.
  • Strengthened its reputation and stature among domestic and international admissions markets while, at the same time, increasing financial aid.
  • Maintained the Alf Museum’s standing as a preeminent institution as well as the leading and only accredited paleontology museum curated by, and on the campus of, a secondary school.
  • Experienced significant growth in its endowment.


Looking to the Centennial and beyond, the Board seeks to ensure that the next Head of Schools has the necessary skills, work experience and inspiration to build upon the school’s strong trajectory and momentum. Our new Head must have the highest levels of integrity and moral courage, as well as a passion for Webb’s unique boarding & day program and culture. Our new Head must also be a community builder and leader who is able to drive the innovation, curricular advancement, and technology opportunities that will lead Webb into our next 100 years.

To help us identify and prioritize the desired leadership qualities, Educational Directions – an independent school search and consulting firm – will be engaging the entire Webb Community with a survey in the near term.

The most important responsibility for the Board of Trustees is attracting, hiring, evaluating, and retaining the Head of Schools. Your Board takes this responsibility seriously and is working proactively to manage the selection process.

The Board Chair, Mr. Sanjay Dholakia, along with Dr. Wendin Smith, are co-chairing a Selection Committee that is working with consulting firm Educational Directions. The Board has charged the Selection Committee with conducting a thorough process to identify the strongest possible candidate for appointment as the next Head.

In addition to Educational Directions, the Board has also 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.

As part of the initial process, the Selection Committee has asked Educational Directions to compile a list of highly qualified potential new Head applicants that represents diversity of gender, race, religion, thinking and sexuality.

In addition to the new Head search, Webb has engaged the Glasgow Group to evaluate all our hiring practices from a DEI perspective.

Finally, the Head of Schools selection is only part of the Board’s commitment to DEI. The Board remains committed to building a community that fosters an inclusive school characterized by openness, acceptance, and empathy, where all members are valued, respected, and supported. The school is committed to DEI long-range goals in all hiring, retaining employees, and in crafting and delivering student experiences that reflect and embrace those objectives. The Board will attract and retain trustees from a broader spectrum of potential members.

The Board of Trustees agrees with the recommendation of our Educational Directions consultants, Mr. Chris Arnold and Ms. Amy Richards, that the search for the next Head of Schools should begin within the organization and with our Associate Head of Schools, Dr. Theresa Smith. The timeline for Mr. Stockdale’s transition to Head Emeritus allows for a thoughtful examination of the leadership potential already in place at Webb as well as outside candidates.

The Board and Selection Committee are committed to an inclusive search for our new Head. We will seek input from the Webb Community throughout, including via formal and informal channels. All Community members will receive a survey, and there will be opportunities for open discussion through Zoom focus group meetings with our consulting leads. We will be posting updates to the website and communicating with the Community at periodic intervals. Please feel free to contact any member of the Selection Committee at any time during the process.

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.

This process will consider options that range from conducting a national search to evaluating our current Associate Head of Schools, Dr. Theresa Smith.

Educational Directions has advised the Board to evaluate our potential internal successor first while it sources potential external candidates.

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.

Webb was founded in 1922. The Centennial will be celebrated in 2022.