Webb Community Honors Head of Schools Taylor B. Stockdale

Webb leaders honored retiring Head of Schools Taylor B. Stockdale for 35 years of service to the organization during an emotional program on Feb. 17, thanking him for leading efforts to double the campus footprint, re-imagine the academic focus and deepen a commitment to educating morally courageous leaders.

“Head of schools is truly one of the most complex jobs you can imagine. The true measure of an incredible leader is someone who makes it look easy,” said Sanjay Dholakia, chair of the Webb Board of Trustees. “Taylor deserves every accolade and 10 more.”

Dholakia said Stockdale’s commitment to Webb has transformed the school and its community.

“Over the last decade, our stature in the world has doubled,” Dholakia said. “This doesn’t happen alone – but there has to be somebody who inspires. Taylor inspires. Taylor creates connections with his ability to put people at ease with a smile or a word. One of Taylor’s gifts is to be able to create community everywhere he goes.”

In recognition of Stockdale’s impact, Webb has named its newly renovated Community Center, which sits at the center of campus, the Taylor B. Stockdale Community Center.  The honor captures Stockdale’s unwavering support of community life.

The announcement was made at a triennial leadership dinner honoring Stockdale and attended by Webb’s Board of Trustees, the Alf Museum Board of Trustees, the Webb Alumni Council, leaders of the Affiliates parents group, senior staff and faculty, and alumni.

Stockdale was stunned by the honor.

“This I did not expect at all. I’m still totally in shock,” he said.

Stockdale thanked his wife, Anne, and children, Claire and Bailey, who were raised on the Webb campus, Dholakia and other leaders of the Board of Trustees. He also recognized his mentor at Webb, former Head of Schools Susan A. Nelson, for whom he served as assistant head of schools and director of institutional advancement over nearly two decades.

Nelson praised Stockdale for his impact on Webb.

“From the moment I met him, I knew that Taylor was destined for school leadership. What I didn’t know was that he and I would have the special gift of a long and enduring friendship,” she said.

Nelson recounted travels with Stockdale to visit Webb alumni, friends and supporters across the globe.

“It’s difficult to describe Taylor’s impact because he excelled in so many different arenas. In all the challenges that he was faced with, he not only fulfilled needs and expectations – he exceeded them. He worked very, very hard to do that. It was a joy to work with him.”

Stockdale built a community of dedicated alumni and supporters as well as strong faculty and staff committed to elevating Webb, Nelson said.

“Taylor raised the bar on people’s expectations for what Webb could be and would become,” she said. “Thank you, Taylor, from me and from all of us. You’ve done great.”

Dean of Faculty Michael Szanyi said Stockdale embodies Webb’s mission, inscribed in stone at the entry to the campus.

“You have thought boldly, mindfully and creatively about how to continue to propel Webb into a prosperous future,” he said. “You acted with honor and moral courage. You led with distinction. And, it goes without saying that you continuously served with a generous spirit year after year. You’ve demonstrated your leadership, commitment and love for the Webb community.”

Stockdale will become head emeritus in July, when Head Elect Dr. Theresa Smith becomes Webb’s seventh head of schools. Smith, who worked for 12 years alongside Stockdale as his assistant head of schools and then associate head of schools, also voiced her admiration.

“You’re genuine and you’re real. I admire your tireless work ethic, all the behind-the-scenes planning that often goes unnoticed – that you let go unnoticed. I admire the way you take time to express gratitude, to make people feel seen for their contributions and to recognize the way people’s efforts help to build up this community.”

Stockdale’s leadership ensured Webb has successfully navigated political, cultural, social and health challenges – including the pandemic, Smith said.

“Your steadfast resolve held this community together and encouraged us all to continue going,” she said. “You never worried about making the popular decision or making the easy decision. You took the time, and you were thoughtful and deliberate and you worried about doing what was right. Day in and day out, you modeled a clear and unswerving devotion to Webb’s mission and the enduring values embedded in it.”