At a time when many schools are grappling with how to re-engage young men, South Kent School is offering something increasingly rare: proof that a boy-centered education can work, and is working.
“We’re not surprised that South Kent is growing,” says Head of School Brian D. Sullivan. “We’ve built something intentional, and the outcomes are real.” In the past year alone, the School has seen a 20% jump in enrollment, the highest boarding numbers in the School’s history, and a sharp rise in applications. Donor support and bequests are also steadily rising, as alumni are increasingly more engaged as stewards of the School’s future. At the same time, South Kent continues to earn national recognition for its mission-aligned programs, high-impact mentoring, and commitment to forming young men of purpose, resilience, and integrity.
While headlines often dwell on the so-called “crisis” in boys’ education, Sullivan prefers a more grounded view, one rooted in observation and experience. “Boys aren’t broken,” he says. “But they do need an environment that understands how they learn, how they connect, and what helps them grow.”
Recent data from Georgetown’s Center on Education and the Workforce echo this point: many young men are making rational economic decisions to pursue trades or bypass college altogether, not because they are disengaged, but because they are navigating a shifting landscape with different pressures than their female peers. In that context, schools like South Kent offer more than just academics; they offer clarity of purpose and pathways to opportunity.
That purpose is baked into South Kent’s model, from a curriculum that balances intellectual rigor with hands-on learning and executive functioning support, to a culture that values leadership, ethics, and adaptability. “It’s about building young men who are confident and prepared—not just for college, but for life,” Sullivan says.
South Kent’s growth is not accidental. It is the result of 101 years of refinement. Sullivan leads with a sense of optimism, not alarm. And in a world increasingly hungry for real solutions, that optimism feels not only refreshing, but necessary.
The school’s model is intentionally balanced; blending structure with flexibility, rigor with movement, competition with compassion. It’s a formula that works. South Kent graduates leave with a clear sense of who they are and what they stand for. They go on to top universities, serve in the military, become entrepreneurs, study medicine, play professional sports, and lead with integrity in all walks of life.
Looking ahead, Sullivan’s vision is bold but focused: by 2028, he wants South Kent to be known as one of the best small all-boys schools in the country. “We’ll stay intentionally small, unapologetically mission-driven, and fully committed to educating the whole person: mind, body, and spirit,” he says.
Fundamentally, South Kent stands for character. The school believes in simplicity of life, self-reliance, and directness of purpose. “This should be a place where boys grow into good men: resilient, grounded, and ready to serve the world with confidence and conviction,” Sullivan envisions.
A Journey Toward Purposeful Leadership
Sullivan became the tenth Head of School at South Kent in July 2023. His path to leadership was shaped by a lifetime of learning, teaching, and service. Raised in a family of educators that valued character, education, and faith, Sullivan has always believed in the power of schools to shape lives.
He experienced the impact of a boarding school education firsthand as a student at The Hotchkiss School, where he was also the recipient of financial aid. It was during this time that he realized the impact a community of educators, who truly know each student, can have on a students life trajectory. From there, he went on to study economics and organizational behavioral management at Brown University. He later earned a Master of Science in Education with a focus on Educational Leadership from the University of Pennsylvania.
Before stepping into education, Sullivan began his career in finance, working in wealth management and investments. That early experience taught him the value of long-term vision, strategic planning, and data-driven decision-making. But over time, he realized that his true passion lay elsewhere. “I came to understand that the most meaningful investment we can make is in people, especially young people. Education offers something no market can match: the opportunity to change lives in real time,” he reflects. “Growing up, I saw firsthand how my father, as a teacher and coach, connected with students in powerful ways. He didn’t just teach them skills, he taught them responsibility, commitment, and work ethic. Most importantly, he gave them hope.”
That realization drew Sullivan to the classroom. He started his teaching career at Boston Collegiate Charter School, followed by roles at Millbury High School and Berkshire School. In 2014, he joined Kent School, where he used his finance background to introduce new instruction in business and financial literacy. Over the years, he served in various leadership positions, including Class Dean, Assistant Dean of Students, Director of Admissions, Assistant Head of School, Associate Head of School for External Affairs, and Director of Development.
By the time he arrived at South Kent in 2021, he had developed a clear perspective on what strong schools need to succeed. He shares, “My professional experiences in finance, the classroom, and school administration give me a unique understanding of what makes institutions and students successful.” Sullivan’s leadership is rooted in a deep respect for South Kent’s mission, history, and community—alongside a clear-eyed focus on the future. “I’m committed to a forward-thinking educational model that engages the whole student with an innovative curriculum for the next generation of learners,” he asserts. “The world is changing rapidly, and the science behind education and the brain has never been stronger. As educators we must be willing to adapt our educational models to build the skills our students will need for their world, while also ensuring our students learn to think critically, communicate with clarity, and remain curious to the world around them.”
Sullivan lives on campus with his wife, Liza, a career educator and college counselor at Kent School, and their two young sons.
Building Culture Through People
One of the most important lessons Sullivan has learned as a school leader is that leadership is not about a title or having all the answers. It’s about asking the right questions, listening carefully and viewing challenges through various lenses and perspectives. It’s also about earning trust, day by day. He recalls, “When I first arrived on the Hillside, I knew we had strong bones. But I also knew we had work to do: to restore clarity, to rebuild momentum, and to continue to reconnect our community with our mission.”
That work has taken time and intention. It has meant having honest conversations, supporting the faculty, listening to alumni, and including students in decisions that shape the school they are part of. “I’ve learned to lead by listening, with empathy and intention, so I can truly understand our people,” he explains. “That means empowering faculty, honoring the stories of our alumni, and inviting students into the process of shaping the school they want to lead,” he explains.
For Sullivan, alignment is key. When people, program, and place come together with purpose, real progress becomes visible. “Small, mission-driven schools can move mountains when they’re aligned around a clear purpose,” he says. What’s become even clearer to him since becoming Head of School is that everything starts with people. “You can have the most beautiful campus, the strongest mission, and the best intentions in the world; but if you don’t have the right people in the right roles, the school will never reach its potential. Period,” asserts Sullivan.
Leadership, he says, requires vision and discipline. But it also requires a deep understanding that a great school is only as strong as its team. He relates closely to something Steve Jobs once said: “Recruiting allows you to have an impact not just on the organization, but on the lives of the people who join it.”
“That resonates with me,” Sullivan explains, “because every time we bring someone new to the Hillside—whether it’s a teacher, a coach, an administrator, a cook, or someone on the facilities team—we’re not just filling a job. We’re shaping the student experience, strengthening our culture, and defining the kind of community we want to be.”
At South Kent, the impact of the right hire can be felt across campus. When educators are driven by purpose, curious about learning, and genuinely committed to the growth of young people, that energy spreads. It shapes the way students participate in class, the way teams train together, and the way faculty support one another. “Culture isn’t created from the top down. It grows—person by person, hire by hire,” affirms Sullivan.
South Kent has made it a priority to bring in people who are not just qualified, but also deeply aligned with the school’s mission and values. These are people who find real meaning in their work. And according to Sullivan, that shared purpose shows up every day—in conversations, in classrooms, and in the way students respond. “The people at South Kent believe in what this school stands for. They enjoy what they do, and they see results. That’s powerful. It inspires our students, because boys model what they see and that starts with our employees,” he states.
For Sullivan, the team at South Kent is equally talented and transformative. “I’m deeply grateful to work alongside such dedicated people who make our school more extraordinary every single day,” he shares.
Leading with Empathy and Intention
Boarding school shaped Sullivan in lasting ways. It taught him independence, helped him build strong relationships, and prepared him to face challenges with confidence. That experience stays with him and guides how he leads South Kent today. “I understand the transformative power of this environment. But I also understand how vulnerable it can feel for a young person to leave home, to struggle, and to grow in real time,” he explains.
At South Kent, boys are given the space to talk openly about mental health. They learn that kindness is strength. They discover that leadership is rooted not in ego, but in service. “We give them room to fail, reflect, and rise,” Sullivan says.
Sullivan leads with empathy because he has lived it. He knows the difference it makes when an adult believes in you—when someone takes the time to say, “I see you. I believe in you.” That simple message had a profound impact on him as a student, and now, it shapes his leadership philosophy.
His goal is to make sure every boy at South Kent feels supported. He wants the structure around each student to be strong, and the adults in that structure to be fully present. He also looks to hire people who share this mindset. “I like the saying, Acta non verba—deeds, not words,” he adds.
Sullivan’s leadership is grounded in what South Kent calls its Trinity of Values: simplicity of life, self-reliance, and directness of purpose. These are not abstract values. They guide the daily decisions on campus. Simplicity of life, he explains, is about staying focused on relationships and purpose, not distractions. Self-reliance means helping students grow through their challenges, not avoid them. And directness of purpose, as Sullivan explains, “Reminds the entire community that the path to success is not a straight line, there will be challenges and obstacles, but if we stay true to our mission and our values, keep our students as our focus, we will be able to adapt and find success to stay aligned with the mission and keep students at the center of every decision.”
Sullivan says. “I lead with transparency, conviction, and compassion. I always come back to one core question: Will this decision help our students become thoughtful, capable, resilient young men?” If the answer is yes, the school moves forward. If not, he’s willing to pause, reflect, and adjust course.
Looking ahead, Sullivan hopes to leave a legacy of intentional growth. He wants South Kent to be remembered as a place where boys are not only educated, but transformed—prepared to live with purpose, curiosity, and integrity. “I want our students to leave here ready to lead and serve in a complex world—not just knowing what to think, but understanding how to live with purpose,” he says.
He also hopes South Kent continues to be a place where teachers feel inspired, where alumni feel proud, and where the mission stays clear and strong. His vision of success doesn’t focus on buildings or recognition. It centers on people. “My legacy is not about headlines. It’s about the lives we’ve touched, the boys who came here unsure of themselves and left ready to lead, serve, and make a difference. That’s the story I want South Kent to keep telling. That’s the legacy I hope to help build. Acta non verba,” he declares.
Tradition with Purpose, Innovation with Direction
At South Kent, tradition is active and intentional and it’s something practiced. The school’s core values—Simplicity of Life, Self-Reliance, Directness of Purpose—continue to guide daily life on the Hillside. But those values are not frozen in time. Their meaning evolves as students grow and the world around them changes. Sullivan shares, “Our history gives us clarity. It reminds us who we are. Innovation allows us to respond to the question: Who must we become?”
For Sullivan, the balance between tradition and progress is essential. South Kent doesn’t aim to replicate the past with new tools. “We’re not trying to build the school of yesterday with better Wi-Fi,” he explains. “We’re building the school that today’s young men need—emotionally, academically, and globally.”
That mindset shapes every part of the academic model. South Kent continues to uphold long-standing practices like weekly Chapel, the jobs program, environmental stewardship, and personal accountability. But it also invests in forward-looking programs like experiential learning, technology education, entrepreneurship, and financial literacy.
A strong educational model, Sullivan says, starts with a simple question: Who will our students need to become? It’s not just about what they need to know. It’s about what they will need to thrive in a fast-changing, uncertain world. This has led to key investments across campus. South Kent has expanded experiential learning at its North Campus–an agricultural, culinary, and science hub—launched partnerships with Syracuse University to offer early college credit, and introduced a reimagined advisory program focused on leadership through the Stockdale Leadership Program.
“We’re preparing students not just for college, but for complexity, for citizenship, for leadership,” states Sullivan. That includes both future literacies like innovation, tech, and global fluency and human literacies, such as collaboration, emotional awareness, and resilience. Sullivan wants South Kent graduates to leave with real-world skills and the confidence to use them with purpose.
This vision is reflected in how the school community works each day. In its most recent accreditation review, the New England Association of Schools and Colleges (NEASC) recognized the authenticity of South Kent’s culture. The review noted: “There are a lot of schools with noble missions and aspirational values, but the members of South Kent School truly personify the Trinity of Values—Self-Reliance, Simplicity of Life, and Directness of Purpose… These aren’t just statements on a wall or website; they infuse every interaction and aspect of South Kent’s daily life.”
For Sullivan, that kind of feedback matters. It shows that the school’s mission isn’t just written but lived. He explains, “This recognition affirms not only how we understand the future and our place in it, but also the responsibility to build a community that reflects and supports this rare and powerful culture.” At the center of that work is a daily commitment to forming young men of purpose, resilience, and character. It’s what defines South Kent and it’s what continues to drive its future.
Raising Boys with Purpose
The commitment to all-boys education is intentional at South Kent. The school’s programs are built specifically for how boys grow, learn, and connect. For Sullivan, that focus is foundational. “We are an all-boys school on purpose and with purpose,” he says.
That purpose is clear in every part of the student experience. The academic structure supports how boys learn best—through consistency, movement, mentorship, and meaning. Programs like the Stockdale Leadership Program, named after Admiral James Stockdale, whose sons attended South Kent, are central to this vision. So are future-focused electives that help students build resilience, form identity, and find purpose.
South Kent is also meeting an urgent challenge: the emotional health of adolescent boys. At a time when anxiety, isolation, and disconnection are on the rise, the school is committed to teaching students that strength includes self-awareness. “Strength is not found in silence. It’s found in knowing yourself, and being open to growth,” states Sullivan.
The goal is to develop young men who are emotionally healthy, intellectually curious, and morally grounded. That also means creating a space where students can laugh, explore, and stay curious about the world. “If one loses a sense of curiosity, the sense of wonder is also lost,” Sullivan adds. “And to lose a sense of wonder is deadening.”
While college is an important milestone, South Kent sees it as just one step in a much larger journey. The school’s curriculum prepares students for a world that is fast-moving, deeply connected, and full of moral and social complexity. To meet that reality, the academic program emphasizes adaptability. Students learn through interdisciplinary classes that connect science with climate issues, economics with entrepreneurship, and history with ethics. The goal is to develop critical thinkers who know how to apply what they learn in real life.
Thanks to South Kent’s partnership with Syracuse University, students can earn college credit before graduation. That early exposure gives them both academic confidence and a head start. But as Sullivan points out, it’s not only about content. “We teach them how to lead themselves, how to fail and recover, how to build relationships across cultures and disciplines. We’re equipping them not just to succeed in a classroom, but to lead in life with curiosity, courage, and conscience,” he explains.
At South Kent, character development is not an add-on. It’s embedded in everything, from Chapel and dorm life to athletic fields and advisory sessions. The belief is simple: boys are shaped by their routines, their relationships, and the choices they make every day. Students are taught that success without integrity doesn’t hold meaning, and that leadership without humility can be harmful. Through programs like Stockdale Leadership and student-led initiatives, boys learn to take responsibility, show up for others, and grow through honest reflection. “Character, for us, is not about perfection,” declares Sullivan. “It’s about persistence, purpose, and the willingness to do what is right, especially when it is hard.”
Tools, Access, and the Future We’re Building
Sullivan brings a background in finance to his role at South Kent. That experience has shaped how he views resources—not as an end in themselves, but as tools to serve a greater purpose. “I think of money not in terms of greed or accumulation, but as a tool. It’s what you do with it that matters,” he says.
That same thinking applies to technology at South Kent. The school doesn’t treat tech as a distraction but as a tool used intentionally, and with balance. Students are introduced to innovation in ways that align with the school’s human-centered approach to learning.
From hands-on coding and robotics to filmmaking and digital design, students are actively building skills that connect to the world around them. Partnerships like the one with Syracuse University give them access to early college courses, while in-house projects offer real-world application.
The North Campus is one example. Reimagined as a living lab, it’s where students engage directly with environmental science, agriculture, and sustainability. Whether they’re planting a garden or working on a team project, they’re building both knowledge and confidence. “From designing apps and filming documentaries to planting gardens from scratch,” Sullivan reflects, “our students are learning by doing and more importantly, learning who they are in the process.”
He recalls a recent example when a group of students took the initiative to update the school’s interactive map online. “They got interested, they got curious, so they tinkered with some ideas and improved what was right in front of them. That is really the best.”
Looking ahead, Sullivan believes schools must evolve quickly to meet a changing world. Technology, economics, and global dynamics are all shifting rapidly. Education, he says, can’t just keep pace—it needs to help lead. That’s why South Kent is moving toward skill-based learning. Academic rigor still matters, but so does emotional resilience, global awareness, and ethical thinking. The curriculum is being shaped to support all of that.
Sullivan asserts, “We are investing in future literacies: technology, innovation, emotional intelligence, and financial fluency. But more than that, we’re cultivating a mindset, one that embraces ambiguity, values collaboration, and remains grounded in purpose.” The goal is not only to prepare students for college, but for a future that doesn’t fully exist yet. South Kent wants them to be ready to shape that future with clarity, wisdom, and courage.
That vision also includes access. South Kent is committed to offering an exceptional student experience, not just to the privileged few, but to all who align with the school’s values. “We’re building a school with an elite student experience—not just a school for the elite,” Sullivan says.
Character, curiosity, and leadership potential can come from anywhere. To support that, the school has expanded financial aid, strengthened international recruitment, and continued to welcome students from all backgrounds who share the mission.
Excellence at South Kent is not defined by status—it is defined by potential. That commitment extends beyond admissions. The inclusion is also about the culture the school creates, where every student is respected, challenged, and given the opportunity to grow. “This is how we build a stronger, truer community, and a better world beyond our Hillside,” concludes Sullivan, a leader who believes that real progress in education starts with purpose, is driven by people, and always centers on the growth of the whole student.
For More Info: https://southkentschool.org/