The son of educators, Tyler Casertano grew up on two different prep school campuses. But when it came time to choose a career, he wanted to try finance. “I didn’t know if my interest in education was born out of comfort, so I went to work on Wall Street,” says Casertano.
He lasted a year.
In 2009, Casertano was hired as a teacher and coach at St. Albans School in Washington, D.C. By 2019, he was St. Albans’ assistant head of school for advancement and strategy. This fall, he begins his role as the Haverford School’s 10th head of school, completing an arc that’s made perfect sense—and is a world away from lower Manhattan.
Casertano is taking over at an interesting time in the school’s history. Haverford’s campus overhaul has been complete since the debut of its new middle school in 2020. So there’s no need for an immediate capital campaign to fund facilities. The school has also closed on a $20 million property in Radnor—43 acres that could reshape its footprint in the coming years. And after years of struggling with enrollment issues in its lower school, Haverford appears to be rebounding.
Casertano’s job won’t be easy. Leading a $40 million operation with 150 employees never is. But the Ivy League-educated 36-year-old has the luxury of few distractions as he concentrates on curriculum, faculty, staff and, of course, the school’s 950 boys. He’ll even be teaching history to ninth-graders this year.
It’s all part of the board of trustees’ plan to make Haverford “the best boys’ day school in the country,” says board chair Maurice Glavin.
“We want to be the best school for boys,” Casertano adds.
And that’s a subtle—but important—difference. It’s one thing to have the facilities, programs and faculty to stake a claim as number one, and quite another to ensure that every student benefits. At a time when nothing fits everyone, Casertano and Haverford are trying to craft an institutional culture that favors individual growth. “A sense of community and togetherness can exist on a really good boys’ school campus,” Casertano says. “That can transcend who you can be friends with, the classes you take, or the sports you play. My hope is that the sense of community allows boys to engage on a deeper level, so they can grow.”
For its previous two heads of school, Haverford turned to Joe Cox and John Nagl, both decorated U.S. Army veterans. In that regard, Casertano signals a return to the civilian model.
For its previous two heads of school, Haverford turned to Joe Cox and John Nagl, both decorated U.S. Army veterans. In that regard, Casertano signals a return to the civilian model. “Sometimes, you have a tendency to go with what works, and sometimes that tendency is a pendulum that swings from one side to the other,” says Bart Smith, an alum, a trustee and the head of the most recent search committee.
In lieu of military credentials, Smith’s committee sought out someone with a strong educational background and experience at a boys’ school. Casertano was a perfect match, having served St. Albans’ all-male student body as a history teacher, a lacrosse, soccer and hockey coach, an admissions counselor, and a development officer. “One thing that stood out about Tyler relative to other people he was competing with was his high emotional intelligence,” Glavin says. “His EQ is amazing.”
It doesn’t hurt that Casertano is on the young side. He and his wife, Annie, are also the parents of 7-year-old Mac and 4-year-old Bailey. “In my own perception of other people’s perceptions, I knew my age would be something that was an aspect of their idea of my identity,” he says. “But people don’t make me feel aware of it. I’m fortunate to have experience at other schools—especially St. Albans—and I’ve drawn on that. I’m not old by years, but I have experience.”
It’s worth noting that Casertano didn’t attend an all-boys institution, graduating from Loomis Chaffee, a coed boarding school in Connecticut. He earned a history degree from Yale University and a master’s from Columbia University’s Klingenstein Program for Independent and International School Leadership. But as you might expect, he’s committed to single-sex model, believing that coed schools don’t always allow boys to show compassion and emotion and express themselves in the arts and humanities. “At St. Albans, I saw the magic that can happen when you give boys the chance to be full versions of themselves,” he says. “I think one of Haverford’s strengths is its commitment to its mission—it has a strong sense of self.”
Casertano is also encouraged by the school’s eagerness to embrace growth. “Haverford is not scared of change, but every decision must be made through our mission for the boys,” he says. “While I hope my leadership and some of the new opportunities enhance the mission, that doesn’t change who we are and what we do.”