Introducing Head of School Tyler Casertano

He likes to take in the “ambient noise” of the campus. It gives him energy to see people working through a project or solving a problem together in a classroom. More than once he’s been found listening in on a Middle School math lesson. Recently, he took the Haverford/EA Day Sweater for a tour of the Lower School, leading to squeals of delight from Haverford’s youngest students.

It’s a quiet leadership trait that serves him well in his first year as Haverford’s Head of School. While he’s becoming acquainted with The Haverford School, its culture, and its many traditions, he already knows a startling number of students’ names, offering fist bumps and words of encouragement to boys and faculty alike as he tours campus.

“He cares about and comes to know every student. His classes seemingly always started with a sort of banter about a student’s performance in a choral concert, or a big play made on the field,” said Sherry Rusher, Dean of Faculty at St. Albans School and longtime friend and colleague of Casertano. “He’s keeping track. He pays attention. As a result, you’d find a wide variety of boys seeking his advice on one thing or another. He became a safe space for boys to be themselves. He’s certainly doing the same at Haverford.”

He’s building relationships, one walk at a time.

Tyler Casertano became Haverford’s Head of School—only it’s tenth since 1884—on July 1, 2021. He inherited a School in a strong position, complete with a new, state-of-the-art Middle School and a team of extraordinary faculty members.

Casertano has dedicated the beginning of his tenure at Haverford to learning from his faculty and staff and to supporting the boys, both of which require strong relationships and trust.

“Relationships can allow someone to recognize their best self,” said Casertano. “It can allow a boy to have a fuller understanding of his abilities and the courage to pursue those abilities. I want to foster that in all our students.”

A CALLING Casertano’s love for being in the classroom runs deep. So deep that he’s making time in his tight schedule to return to the classroom as an Upper School history teacher in the 2022-23 school year.

“I like understanding who the kids are and what they need. I like meeting them where they are,” he says.

This fall, Upper School boys in Mark Fifer’s U.S. History class got a preview of what it is like to be Casertano’s pupil. He almost visibly sinks into the role of teacher, removing his ‘Head of School hat,’ and replacing it with a well-worn and well-loved ‘teacher hat.’

In a lesson about indigenous peoples and civilizations of North America, of which Casertano is an expert, he seamlessly crafts a story about the sophistication of Native American civilizations and the incorrect perceptions that unfairly perpetuate today. He weaves in a broader global conversation to his lesson, bridging to how trade, globalization, geography, and invention impacted these civilizations and how we remember them.

The boys react with interest and with thoughtful questions. They see their Head of School in a new light. In a single afternoon, Casertano walked into the classroom and humbly added another brick to the foundation of a relationship—this time with the boys.

A PARTNER AND A FRIEND “I’ve often said that my mother—with a small bit of help from my father—built a great school at Millbrook,” said Casertano, with a smile. “My parents certainly modeled how to support one another and to be a team.”

It’s that sense of partnership, of teamwork, that permeates Casertano’s interactions with everyone he meets on Haverford’s campus. It’s a hallmark of his personality; an indicator of him as a leader, and apparently a familial trait.

“In one word, Tyler is steady,” said Brendan Sullivan, a member of St. Albans Governing Board who worked closely with Casertano on their Strategic Plan. “He shows up when you need him, when you expect him, and even sometimes when you’re not expecting him. He does it all with quiet humility and always in service to someone else.”

Casertano feels the support of his family, while also recognizing the support that he must give in return. He notes that his wife Annie’s career in real estate development is of major importance to him.

“Annie and I have often reversed the stereotypical gender roles when it comes to our careers,” he said with a laugh. “She goes to work in a hard hat on construction sites, while I go to work as a teacher. She has been very successful in a traditionally maledominated industry, and it is important to me to support her career, too, in this move to Haverford.”

He calls Annie, who he met at Yale while she attended Trinity College, the strongest person in their family. “She is an amazing

Head of School Tyler Casertano and his father Drew Casertano, the former Head of School at Millbrook School, discuss topics related to their careers, the memories they have of living on Independent School campuses, and of the family who support them. combination of sensitive and tough. She is deeply kind and considerate, while also being resilient and gritty.”

Their children, Mac, who is 6 and in kindergarten at Haverford, and Bailey, who is 3 and attends The Haverford Center, are enjoying time on Lancaster Avenue and are delighted when they see Dad on campus.

ON LEADERSHIP:

TC: I admire my dad’s resilience and range of leadership. He shows a great deal of courage. He took over a school that wasn’t in great shape, and the first eight years there were hard for him as he righted a massive ship. I still find inspiration in his range of interacting with others and his ability to connect with people in such an authentic way.

DC: I think Tyler has a lot of those qualities, too. Tyler combines thoughtfulness with intention and team building. He’s got a very clear vision of what a great school should be, but he also sees that it takes time. I think he has a good idea of what he needs to learn and how to know the institution.

ON THE ROLE OF PARTNERS:

DC: Having a strong partner is everything. My experience was very much a partnership with Linda, and she had a strong career of her own. When we went to Millbrook in 1990, she cried the entire way there—she was sad to leave the life we created at Loomis Chafee— but she was with me every step, regardless.

TC: Annie is so special. We are each other’s best friends first and foremost, and we have a true partnership. I had a great example

Bailey, in reference to the candy dish outside Casertano’s office, thinks her father gets to eat candy all day with his friends. Mac, while not entirely correct, seems to be onto something: he thinks his dad walks around all day.

“I love bumping into them while I’m around campus,” says Casertano. “I underestimated how powerful and rewarding it would be to have them here with me. Watching my children become part of the community has been one of the most fun parts of this process. They’re excited to go to school every day and so am I.”

FOR THE BOYS Casertano has a track record of making school a place to look forward to for his students, even on the days that are hard for them.

“Tyler was the featured speaker at a Governing Board retreat — giving a major presentation on the Strategic Plan. It was vital for the presentation to go well,” said Joe Viola, Director of Admissions at St. Albans School. “We were driving together, and I anticipated a quiet, reflective ride. I got something very different.”

Instead of reviewing notes of his presentation or thinking through possible questions from the Board, Casertano spent the entire hour-long ride on the phone with a student who was having trouble in a class.

“On an extremely important day of his professional life, he made the choice to be there for that student. It spoke volumes about Tyler’s leadership,” said Viola. “He capably handles all parts of his job without losing sight of the things that are most important: his family, his students, and his colleagues.”

This is the same energy Casertano exhibits each day at Haverford. He has a strong focus on learning the School and its traditions, but his priorities and goals lie with the boys and the faculty that support them. His walks are a conduit for connection, a deeply intentional leadership approach that results in strong, meaningful ties in the classroom, in his family, and as a leader.

of balancing careers with my parents. I aim to support her and be invested in her and our children’s lives just as much as they are supporting me in my role at Haverford.

DC: No Head of School can succeed without a supportive, tough, and courageous partner. Linda—and now Annie—are courageous that they left jobs they loved and communities they loved and went to new places. That’s love.

ON MEMORIES:

TC: I recall having a lot of independence on Millbrook’s campus. It was all we knew, but I remember it dawning on me that my brothers and I had access to these amazing resources. We would have birthday parties in the art studios or the hockey rink. It presented non-stop stimulation. I’m glad my children got to experience some of it; I have a photo of Mac petting a panda at the school’s zoo when he was two. I’m seeing my children now get the opportunity to explore Haverford’s campus with new friends.

DC: I do remember us getting to Millbrook’s campus and some faculty children coming over and asking to take a walk with you and your brother. It got to be about dinner time, and you still weren’t back, so I asked the parent of the other child—a faculty member at Millbrook—whether we should go out looking for you. He said “No, they’ll come back at some point.” I think Tyler was about four!

TC: I remember paying a lot of attention to what you were doing as the leader of the Millbrook community. In your office talking with students or faculty, or dictating letters on the way to my hockey practice. Even at a young age I had an interest in what you were doing, and an appreciation for how you were doing it. That was one of the neat parts of growing up on a campus—I got to see my parents in action as professionals.

ON MEANINGFUL WORDS:

DC: Before Tyler’s first day at Haverford, I gave him a handwritten note telling him I was proud of him and telling him that “you’ve got this.”

TC: That note is still on my desk. I look at it often. I have a sign prominently displayed in my office that my younger brother gave me—it says “What good shall I do this day?” I also have a paperweight on my desk with a quote from Winston Churchill saying “These are great days,” which my father gave me to remind me that even the most challenging days are great days. Annie and I created a family mantra for our kids that has stuck over the years—“helpful, happy, nice.”