When Ian Craig stepped onto Shipley’s campus this summer as its 11th Head of School, he did so with a deeply rooted belief in the power of relationships and a steady commitment to what he calls “the work that matters.” With 20 years of experience as a head of school across a range of educational settings, Craig brings to Shipley not only expertise but also humility, humor, and heart.

Born in Montreal and raised on Long Island, Craig is a second-generation educator who took his first job in finance after college. “I was terrible at it,” he laughs. “I hated every minute.” At the urging of his own intuition—and against the advice of his father, a seasoned Head of School—Craig pivoted to teaching. He earned a master’s degree from NYU and completed his student teaching at Stuyvesant High School. “I loved every day,” he recalls. “That’s how I knew I was in the right place.”

From there, Craig’s path led him into leadership roles at schools across the country. Along the way, he has developed a clear sense of what great schools—and great leadership—require: “It’s all about the people. Nobody comes back to visit a building. They come back for their teacher, their coach, their mentor.” This people-first approach informs not only how he hires and builds teams, but also how he defines success for students.

“There’s no one-size-fits-all version of thriving,” Craig says. For some students, success means acing a rigorous course load. For others, it’s about finding joy on the playing field, in the art studio, or on stage. “The best schools,” he explains, “create an environment where all kinds of kids can be seen, valued, and stretched.”

Craig’s leadership is marked by a focus on balance, between tradition and innovation, rigor and well-being, autonomy and accountability. His first priority at Shipley, he says, is to listen: “You can’t lead well until you understand the culture. What matters here? What’s sacred to the community? What do students and teachers care most about?”

Those values—connection, curiosity, and compassion—are precisely what drew Craig to Shipley in the first place. “When people talk about Shipley, they don’t just talk about it as a place of work or study,” he says. “They speak with deep, personal feeling about what the School has meant to them. That’s rare—and incredibly compelling.”

Now living on campus with his wife, Holly, and their daughter, Maia ’37, a new First Grader, Craig is not just leading the community—he’s becoming a part of it. “Being both a parent and a Head gives me a unique lens. I get to see the School from all angles, and I love that.”