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Philip Cocchiola: Nurturing Student Growth Through Individualized Learning


For over a century, the Oxford Academy in Westbrook, Connecticut has stood as a beacon of individualized education, guided by the timeless wisdom of Socrates: “Know Thyself.” At the forefront of this transformative institution is Philip Cocchiola, who has served as Head of School since 2010.

Cocchiola’s journey with Oxford Academy began in 1998 when he joined as a social studies teacher and basketball coach. Even then, the seeds of his educational philosophy were taking root, shaped by the school’s unique one-on-one teaching method and its mission to empower each student to reach their full potential.


“Oxford isn’t just a school, it is a community with one purpose: your success,” Cocchiola affirms. “It is our belief that the most important part of your life is ahead of you, not behind, and we are far more interested in where you want to go than in where you have been.”

This forward-thinking approach is woven into the very fabric of Oxford Academy, which was founded in 1906 with a vision inspired by the mentoring pedagogies of the prestigious universities of Oxford and Cambridge. The school’s one-to-one classroom structure incorporates Socrates’ active, personal approach to inquiry and critical thinking, encouraging students to find their voice as partners in their own learning.

Cocchiola is a fervent advocate for this individualized model, likening it to the experience of an Olympic athlete. “Imagine what a student could accomplish if they had a personal trainer pushing them beyond their limits, challenging them to new heights, and at the same time offering support that leads them to success,” he posits. “Frankly, it sounds like a dream, but I am here to tell you that this dream is a reality, and has been for a select group of students for over one hundred years.”


This unwavering commitment to tailoring education to each student’s unique needs has been a hallmark of Cocchiola’s tenure at Oxford Academy. From the initial admission process, where one-on-one interviews explore a young man’s learning profile, experiences, and aspirations, to the collaborative effort between teachers and students in shaping each course’s direction, personalization is at the core of the Oxford Method.


The results speak for themselves. As Cocchiola notes, “Typically, students begin to flourish after spending a year here. By the second year, they are achieving at higher levels than before and have grown as young men.” The school’s rolling admissions policy allows students to enter whenever space is available, catering to those who have struggled in traditional settings or seek an accelerated pace.


Yet, the Oxford Academy experience extends far beyond academics. Cocchiola himself exemplifies the school’s holistic approach, having lived on campus in various residences throughout his tenure, fostering a true sense of community. “You get to know students really well. It really raises accountability. You know exactly how they’re spending their time,” he reflects. “You really get a sense of making a difference in their lives. And that’s why people teach here.”


This immersive experience is a hallmark of life at Oxford Academy, where faculty members reside on campus alongside students, creating an environment that Cocchiola describes as akin to a traditional boys’ boarding school, but with a distinctly non-traditional teaching methodology.


For Cocchiola’s own family, including his wife and twin boys, living on campus has been a profound privilege. “The real benefit is that I get to see my family during the day. I’m very lucky,” he shares. His sons have been exposed to a rich tapestry of cultures and perspectives, interacting with students from around the globe and fostering a sense of social confidence from an early age.


Cocchiola’s dedication to education, however, was not always a certainty. After graduating from the University of Connecticut with a degree in history, his first foray into the professional world was with IBM. But as he quickly discovered, corporate life was not his true calling. “It took him just two years there, though, to realize it wasn’t what he wanted,” he recounts.


It was then that Cocchiola embarked on an accelerated master’s in education program at the University of New Haven, juggling a full course load at night, student teaching during the day, and working weekends at IBM to make ends meet. As he neared the completion of his degree, a friend who was already teaching at Oxford Academy suggested he join the faculty – a pivotal moment that set Cocchiola on his life’s path.


“The first year here was interesting – teaching, coaching, and residential responsibilities for duty nights,” he reminisces. Yet, it didn’t take long for him to become hooked on the Oxford experience, a passion that has only deepened over the past 25 years.

Now, as Head of School, Cocchiola’s influence extends far beyond the campus grounds. He serves as chair of the Independent Education Consultants Association (IECA) Foundation, co-chair of the Middlesex Chamber of Commerce, Westbrook Division, and on the Westbrook Park and Recreation board.


Despite the demands of his role, Cocchiola remains a lifelong learner, immersing himself in his favorite periods of medieval and Civil War history. He has even indulged his passion by visiting historical sites like Gettysburg, reveling in the stories and insights they offer.

For Cocchiola, however, his greatest source of fulfillment lies in the lasting impact he has on the lives of his students. “We have a community of incredible young men and women who are now shaping the world, and that gives me comfort to know that a new generation of Oxford is making the world a better place.” he beams.


As the world continues to evolve, Cocchiola’s vision for Oxford Academy remains steadfast: to provide an unparalleled educational experience that empowers each student to discover their true potential. “If you want something more from your education, then I hope you will continue to read on and pursue our website and ideally come for a visit,” he encourages. “I have no doubt that you will see that an Oxford Academy education is unlike anything you have experienced before.”


We had a chance to catch up with Philip recently as he prepared for the students’ return after Spring Break.


What is it like for your family to live on Campus with the whole Oxford Academy family?

“It has been a true gift for me and my family. My wife and I consider it a privilege that our sons get to experience a true community where we support one another and true friendships are made. My sons get to meet boys from all over the world who bring with them different beliefs and customs and it has opened their eyes to a wider world and given them a unique perspective on other cultures. I also know that they are more comfortable in social situations as they have grown up meeting and interacting with people of all ages at Oxford events, nightly dinners, sporting events, etc…”


What does your regular day look like?

“My typical day consists of arriving at my office at 7:00 AM and getting a head start on the day. I have a few Oxford boys who are early risers who will come for a visit to chat before everyone arrives in the building. At 7:50 AM, I attend the all-school meeting, and from that point on I am in Knight Hall answering calls, sending emails, or on zooms with various folks. Some are current families, prospective families, or alumni. Sometimes it is meeting with contractors, vendors, etc. Teachers and students are always in my office as well. I also interact with our Oxford community in the halls, classroom, or study hall. At 3:00 when classes end, I typically try to answer a few more emails before I go home sometime around 3:30-4:30. I then go work out, followed by a bike ride if I can or watching my sons play sports or attending an Oxford athletic event. I then attend dinner with my family in the dining hall at 6:00 and hang out there for a while before heading home. Evenings are often busy with Town meetings where I serve on various boards or spend time at home with my family.”


How does your professional goal align with the School’s teaching philosophy?

“I am a firm believer that everyone learns differently which obviously aligns well with our one-to-one and true individualized educational model. As an example, I am a bit of a hobbyist carpenter but I do best building things after I have watched a video on how something was built and then going off of plans. Like our students, I need that information delivered in a way that makes sense to me. Growing up, I navigated a traditional educational model and I wonder how much more successful I would have been had I had the privilege of an Oxford education.”


What does it mean to you to win the SBSA Gorman Award?

“Anytime you are recognized by your peers it is an honor. I was truly humbled and surprised that I received the award but I am a true believer in small schools and what we all do for our families. The award is proudly on display in my office as a reminder to keep working hard to support schools like Oxford and the amazing work that we do.”


What is your most proud moment as the Oxford Academy’s Head of School?

“This is difficult to say because there have been so many beautiful moments over my 25 years here but if I have to single one out,  I would say, ironically, it was also one of our most challenging moments. Navigating the Covid pandemic was one of the most difficult things our community had to get through but everyone came together and we made it through and we are stronger now because of that experience. It has proven to me just how strong and dedicated our community is and that Oxford will be around for many years to come.”


Have you built lasting friendships with the Oxford Alumni?

“As a result of my time at Oxford, I have built hundreds of lasting friendships with alumni. It is one of the best parts of the job, keeping in contact with our families and hearing what they are doing after Oxford. I always look forward to our events or trips when I get to catch up with our alumni, especially the boys I used to teach who are now raising families on their own. We have a community of incredible young men and women who are now shaping the world and that gives me comfort to know that a new generation of Oxford is making the world a better place. I also should mention how supportive our alumni are. We are one of the only schools without any debt (if not the only one) and all improvements to our campus have been made possible by the generosity of our families who believe in what we do but are also so appreciative of what Oxford has done for them.”


With Cocchiola at the helm, Oxford Academy stands poised to continue its legacy of transforming lives, one student at a time.

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