Simon Hess, President, Gulliver Preparatory School

In an interview with Invest:, Simon Hess, president of Gulliver Preparatory School, discussed the school’s commitment to academic excellence, diversity, and innovation. He highlighted recent capital investments, the integration of technology, real-world learning opportunities, and the importance of attracting and retaining top educators to shape the future of education.

What are you most excited about at Gulliver Preparatory School?
One of the most exciting things for me was witnessing the achievement of last year’s seniors. Many had been at Gulliver for 14 or 15 years, and the class was exceptional; not just in the awards they earned but also in their post-secondary destinations. Twenty-seven students were accepted into Ivy Plus schools, and another 150 are attending Top 50 schools nationwide. We also had students head to world-class art schools and institutions in Europe.

At the same time, we welcomed over 200 new families this year, many with children as young as 3. Their energy and enthusiasm are infectious, and it’s exciting to see them begin their journey at Gulliver. Everything at Gulliver starts with the students; they are at the heart of everything we do.

We’ve also had a transformative period of capital investment. We opened our Academic Building, home to our Signature Academic Programs, offering specialized studies in architecture, engineering, entrepreneurship, international law and diplomacy, biomedical science, and more. It’s an incredible, state-of-the-art learning facility, especially at the secondary school level. Next to it, we have a premier outdoor playing field, home to our soccer, lacrosse, football, and softball teams, and we are especially proud of our boys soccer team which won both the state and national championships last year.

Additionally, we recently opened what I believe is Miami’s finest high school Athletic Center. It includes a collegiate-level gym, weight room, training facilities, and locker rooms, along with our Woolworth Family Executive Offices and a new parking garage — an essential resource in our neighborhood. More importantly, these new spaces allowed us to unite all high-school students on one campus, making Gulliver truly one school. It’s been an extraordinary year, celebrating our graduates, welcoming new families, and creating exceptional spaces where learning happens every day.

How does Gulliver foster a sense of belonging among its diverse student body?
With students from so many different backgrounds, there’s always a concern about whether everyone will feel like they belong, are seen, and are valued. One of the most beautiful things about Gulliver is that the answer is a resounding yes. We see diversity as a strength. Families choose Gulliver because they want their children exposed to new ideas, challenged intellectually, and shaped into global citizens. Building that kind of community takes intention. We don’t assume one way of thinking will define our culture. Instead, we actively teach students to appreciate diverse perspectives, experiences, and identities.

Our values – Exploration, Nurturing, Empowering, and Pioneering – reflect our commitment to fostering an inclusive and dynamic environment. These principles guide us in ensuring every student is supported and encouraged to grow.

How do Gulliver’s values contribute to students’ professional and personal growth?
When I first researched Gulliver, the value that stood out to me was “Pioneer.” Many associate it with invention, but I see it more like the pioneers who built this country — visionaries willing to take risks despite uncertainty.

At Gulliver, we embrace that pioneering spirit. The future is unpredictable. I graduated in 1989, but for today’s students, that might as well have been 1889. The world they are inheriting is completely different. And for our youngest students, the world they will enter as adults will be even more transformed.

We must prepare them to be resilient, navigate uncertainty, and remain optimistic. That mindset allows our students to act boldly, dream big, and approach challenges with confidence and heart. It’s something we’re incredibly proud of.

How does Gulliver incorporate technology and innovation into its educational approach?

We focus on balance and thoughtful integration. There’s growing concern about technology’s impact on children, especially with books like ”The Anxious Generation,” by Jonathan Haidt highlighting these issues. While we embrace technology, we also prioritize student well-being.

Our 1:1 device program starts in fifth grade, and even our youngest students have access to technology. Our high school offers advanced coursework in robotics, computer science, and other tech-driven subjects. However, we also teach students to be responsible users. One way we do this is by limiting cellphone use on campus during the school day. Phones are powered off, and we’ve seen a significant increase in face-to-face interaction and deeper connections. We’re proud to put student wellness first, ensuring technology enhances learning rather than distracts from it.

When it comes to AI, we see opportunity rather than just a risk of cheating. I remember when Google first emerged, and schools worried about students using it to cheat. In reality, it expanded knowledge access in incredible ways.

At Gulliver, we encourage students to use AI as a learning tool. For example, they might generate an argument on a topic and then critique it or create mathematical models and analyze their accuracy. These exercises teach critical thinking and digital literacy, essential skills for their futures.

Beyond the classroom, AI improves our operations, from automating meeting notes to helping our finance and development teams analyze data efficiently.

Ultimately, we want students to navigate technology with purpose, embracing innovation while also learning to unplug, interact, and grow as well-rounded individuals. It’s all about balance.

What are some of the biggest opportunities in education right now, and how is Gulliver planning to take advantage of them?
While what happens on campus is incredible – the learning, exploration, and sense of community – there’s an entire world beyond our gates. One of the biggest opportunities we see is expanding learning beyond the classroom, taking students out into Miami, across the state, and even the country.

We actively encourage students to engage with the broader world. Our Model United Nations team competes in Washington, D.C., California, and Tallahassee. Our arts programs showcase talent nationwide through dance, music, visual arts, and performing arts. These experiences expose students to invaluable feedback, diverse perspectives, and the spirit of competition, all of which elevate their skills.

Service is another priority. We encourage students to work with nonprofits and participate in internships, especially in high-need communities.

We’re also focusing on workplace readiness, particularly through our Signature Academic Programs. For example, Digital Mass Media students gain real-world experience in media firms. The goal is to make education more relevant and applicable.

This shift isn’t limited to K-12 education — we see it at the university level as well. Schools like Vanderbilt and Northeastern are expanding into Miami, and co-op programs are becoming more common globally. Education is moving beyond traditional classrooms, and we’re excited to give our students opportunities to apply their learning in the real world while still in school.

What are your main goals and priorities for Gulliver Prep?
We aspire to be an internationally recognized center for excellent teaching and learning. Over the next four to five years, our top focus will be human capital. We’re on the verge of a teacher shortage crisis. Fewer people are entering the profession, and more are leaving than ever. In Miami, rising living costs make it even harder to attract and retain top educators. So, we’re focused on keeping our incredible teachers while recruiting nationally and internationally to bring the best talent to Gulliver. That means ensuring we have the resources to compensate teachers fairly and making Gulliver a true destination workplace. At the end of the day, the quality of a school is directly tied to the quality of its teachers.

This isn’t just a Gulliver issue; it’s an education sector priority. I come from Boston, where there’s a thriving educational ecosystem: the top-ranked public school system in the country, outstanding independent and charter schools, and some of the best universities in the world. Miami, by comparison, is a young city. As it grows, we must invest in developing a strong pipeline of educators, not just for Gulliver, but across all schools, including our independent school and Miami-Dade Public Schools peers.

I have spent 30 years in education, and I firmly believe Miami’s future depends on recruiting, retaining, and developing outstanding teachers. Education is the foundation of a thriving city, and that starts with investing in the people who make learning happen every day.