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Meet Vail Mountain School’s new head of school

A lifelong educator, Steve Bileca is looking forward to furthering community, knowledge and relationships as VMS’ new Head of School

Steve Bileca sits around a campfire in his new office at Vail Mountain School. Bileca started his new role as Head of School on July 1, 2022.
Ben Roof/For the Vail Daily

When you enter Vail Mountain School, one of the first things you’re confronted with is the all-glass office of its head of school. Front and center, the transparent office represents the forthright, exploratory and collaborative nature with which new Head of School Steve Bileca wishes to run the school.

And looking out from the office, Bileca — who joined the school in his role on July 1 — is embraced by not only sprawling views of Vail but of the faces of the community he’s excited to join.

“There is very little in the world that makes me happier than seeing happy kids learning, and seeing happy kids learning in such a spectacular and truly awe-inspiring environment is something that makes me feel like I won the lottery,” Bileca said.



Bileca describes himself as a lifelong educator — with his teaching and learning experiences spanning the country and the world. And for him, this passion and love for education traces back to his upbringing as a first-generation American.

“Both my parents were born overseas and from my earliest ages, my earliest memories, curiosity and questioning were very highly prized in my home,” Bileca said. “And such a great portion of what education is, is just that: How do we develop curiosity and how do we develop the ability to ask these great questions?”

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This philosophy — led by both his parents, but specifically by his mother, who herself was a lifelong public education teacher  — clearly was impactful as he and his three siblings all pursued careers in education.

Bileca joins Vail Mountain School after serving as the assistant head of school for academic affairs at Hackley School in Tarrytown, New York. Throughout his career, he worked on both coasts in roles such as assistant head of campus, dean of students, history department school and as a teacher of Spanish, German, history and philosophy.

His own academic background includes a bachelor’s in modern thought and literature as well as history, a master’s in history as well as a Ph.D. and ABD in modern European intellectual history from Cornell University. In addition, he has studied at the University of Chicago, the University of California Berkeley, and the Freie Universität in Berlin, Germany.

For him, his path to becoming head of school at Vail Mountain School started when his girlfriend — and now wife of 26 years, Angela — took a job as a Spanish teacher at an independent school in Oakland, California. Bileca, who was writing his dissertation at the time, was immediately intrigued by the school and took a three-week job as a substitute there.   

“From the very first moment I stepped in I knew that this was going to be a magical profession, something that would really speak to me,” Bileca said. “By the end of the three weeks, I did a 180 and decided, I love academia, but I think I’d love this more.”

For him, the independent school model embodied not only what he valued and loved about education, but gave him the freedom to construct his own courses and really build relationships — core tenants of his philosophy on education.

“I think all great schools are built on relationships. And the ability to help shape a young person’s disposition toward learning is a great gift and a great responsibility. And learning how to connect with students in that way, for me was eye-opening and something that I felt very deeply about,” Bileca said.  “Having that freedom, together with the founding values of the school, the mission, was something that I felt was very powerful.”

As Bileca’s career progressed as a teacher — staying within independent schools  — he “slowly, over time” entered into more administrative roles where he was able to not only continue teaching but also play a role in shaping schools’ missions and intentionally driving them forward.

In fact, it was Vail Mountain School’s mission — “build community, seek knowledge, develop character” — that initially attracted him to the school and led him to interview for the position.

“Those six words speak so deeply to me and so deeply to what I think great schools are and can be,” Bileca said.

On education

As previously mentioned, Bileca’s philosophy on education began with the value his parents put on curiosity and questioning at a young age. And over the course of his life, as he traveled the globe and became a parent himself, he continued to develop his stance and philosophy as an educator.

While Bileca has taught a number of subjects over the years, there’s one course that he’s developed and taught over the years that embodies why he loves education and is “the most important” to him. Titled “The Good Life, an Introduction to Ethics,” the course explores the prime focus of education to him, he said.

“The prime focus of education is trying to answer the question: What kind of human being should I be? What’s worth striving for? And how can I incorporate others in my journey in a meaningful and productive way in order to reach self-insight and insight into what will make for a meaningful life?” Bileca said. “It’s about setting the right tone and setting the right atmosphere so that they can feel supported and sometimes a little challenged and answering those questions.”

This course — and the questions it poses  — really gets at the core of what education should be, to Bileca. As both a teacher and an administrator, there are three principles that he keeps at the forefront of all that he does.

“One, I meet kids where they are, and take them a little further than they think they can go,” he said. “We need to see children for who they are, what their interests are, what their abilities are, and in the right way, help them go just a little further than they think they can. And it works when children feel a bond of trust. It works when children feel genuine care and it works when children are given the right kind of support from teachers.”

The second, he added is taking what we have learned through brain science about how students learn and applying it in the classroom pedagogically.

“That’s an ethical response that we have to taking what we know and translating it into practice,” Bileca said.

And the third principle is based on an understanding that school is where students — and future members of a participatory democracy — learn how to learn, he said. With this in mind, Bileca emphasized the importance of school being a place to help students learn how to build understanding and listen to others with differing viewpoints and backgrounds.

“Great education, no matter where it is, is about empathizing and giving courage to students to be who they are,” Bileca said. “If you teach children how to empathize with those who are sitting next to them, who may be like them, who may not be like them, and how to have the courage to then be themselves, you can create an atmosphere where great learning happens and where great human beings can be developed.”

As for how these philosophies apply to teachers, the answer is simple, he added.

“I really believe that we want our children, our students, to be lifelong learners. And first and foremost, as teachers, we need to always be learning,” Bileca said. “We model, in everything we do for the students that we have, what it means to be a good learner and a good human. Our role in their development is to help them come to their own insights by engaging them in a process of learning that engages their whole being, really. So we need to be conscious and cognizant of the fact that our interactions with them really mean something.”

On Vail Mountain School

Not only was Steve Bileca drawn to Vail Mountain School by its mission, but also by the outdoor opportunities it offers to student athletes.
Steve Bileca/Courtesy Photo

As Bileca takes this philosophy and seeks to find ways to emphasize it at Vail Mountain School, he sees its six-word mission as the perfect embodiment of education.

From developing character, seeking knowledge and building community, Bileca said that finding “a school where that’s front and center at the heart of what it does to me was just a dream.”

Another aspect that sold him on the school was that Bileca said it was the only school that combined “world-class K-12 education” with “serious outdoor education.”

As an avid outdoorsman himself, he was drawn to the way the school encourages “kids go outside to go inside.”

Ultimately, Bileca said that he took the job at Vail Mountain School because he was attracted “by the reputation of the school and by its mission, by the folks that I met, by the kids, especially that I met during my visits.”

“I see the real focus of my job is to enhance, amplify and extend those things that make the school what it is,” Bileca added.

In no particular order, he said this included continuing to cultivate relationships between teachers, students and parents; continuing to find ways for highly competitive athletes to excel academically; extending the notion of community between all students at the school and finding meaningful ways for them to connect; attracting and retaining quality teachers; finding ways for kids from all walks of life to have a great education; as well as bringing a greater sense of connectivity to the greater community, including through service projects.

“I’m looking forward to helping the school step into its next iteration of itself to write its next chapter,” Bileca said. “The school has so much to give.”

On the future

Steve Bileca with his wife, Angela, and his two sons, Daniel and Alexander. As Bileca readies himself for his new role at VMS, he also is looking forward to exploring all the community and recreation opportunities the valley has to offer.
Steve Bileca/Courtesy Photo

As Bileca enters his first year at Vail Mountain School, he’s looking forward to getting to know the school in a “deep way,” asking questions and really getting to know the students and the community.

“I think it’s early for me yet to say, here is the imprint I’d like to leave,” he said. “I’d like to come to know the school, come to understand on a deep level what our students are looking for and capable of, come to understand our parent community, to build connections with the community.”

While Bileca is looking forward to joining the school with great anticipation and excitement, he’s also coming in ready to face the challenges many schools and educational institutions are facing in the shadow of the pandemic and greater economic turmoil.

For him, these challenges include access and affordability for families and employees. As such, “seeking ways to help make Vail Mountain School as affordable as possible” is high on his list of priorities, he said.

And secondly, it includes addressing the long-term impacts of the pandemic that all educational organizations in the country are facing.

“(Long-term impacts) include impacts on children’s social, emotional and academic development, faculty exhaustion, as well as include the ability of schools to sustain a healthy sense of community,” he said. “Relationships are built one interaction at a time and of course ideally face-to-face. I look forward to inviting our community fully back into relation with one another, and on campus.”

However, overall Bileca is looking forward to embarking on this new experience. Especially, he added, he’s looking forward to taking on the journey alongside his family, which includes his wife, Angela and his two sons, Daniel and Alexander. Moving to the valley, the family is excited about the opportunities for exploration and outdoor recreation, which he said have always held a high value for his family.

“Having a sense that this is a very tight-knit valley community, not just the Vail Mountain School community, but the whole community, we’re really looking forward to exploring all of that,” Bileca said.

Already, the family is embedding itself in all the opportunities the valley has to offer. Not only has the family been hiking and biking local trails and camping (most recently at Piney Lake), but they are all working locally. His wife will begin teaching Spanish to middle schoolers this fall at Eagle County Charter Academy and his two sons have spent the summer working for local fly-fishing outfitters and bike shops.

“The joy that I feel in starting something new and starting something fresh with my whole family would be hard to overstate,” Bileca said. “The excitement that we feel coming into a new community and coming to learn and understand more about what makes the Vail Valley tick is just something that is, for us, endlessly intriguing.”


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