Sara Rubinstein, Head of School, Carrollwood Day School

August 2026 —Invest: spoke with Carrollwood Day School Head of School Sara Rubinstein about an increasingly competitive education landscape, Carrollwood Day School’s IB foundation, and its forward-looking approach to student development. “Seeing students take what we teach in the classroom about global citizenship, critical thinking, and interconnected ideas and apply it on a global platform has been really exciting,” Rubinstein said.

What key changes over the past year have most impacted the school, and in what ways?

When I reflect on this past year, some of the changes that have had the most impact on our community have been the growth of our entrepreneurship initiatives, our AI initiatives, and our global programs.

We worked with a talented team to develop a K-12 AI curriculum. That does not mean we are putting kindergartners directly on AI tools, but we are teaching them the rudimentary basics of data science, such as how to recognize and sort things. As they move into the uses and programming of AI later, we want them to understand that there is nothing magical happening with AI. It is a system that can make their lives more productive, but they need to use it ethically as well.

We have developed character-driven programs around the ethical use of AI, a library of useful and future-ready applications for students transitioning to college, and a deeper curriculum around how students can become the programmers of AI. We want them to understand what it is doing so they are not manipulated by it, but can use it effectively.

On the global programs side, we are part of Round Square, a network of 280 international schools around the world. We have sent teachers to Australia to learn about theater, and I went with students to Dubai for a global conference, Beyond the Dunes, on sustainable future development. We also hosted our first Round Square conference, The Seeds of Ingenuity, which brought students from around the world to our campus to learn how to apply the principles of entrepreneurial thinking to environmental challenges. Seeing students take what we teach in the classroom about global citizenship, critical thinking, and interconnected ideas and apply it on a global platform has been really exciting.

This year, we also launched our Entrepreneurship Institute, where students engage in design sprints to solve problems in our community and the greater world, including a pitch competition at the University of Tampa. They also can join teams through Patriot Labs to practice the problem solving and technological skills they need to thrive in college and beyond on a series of real-world projects designed to help the school and the community.

Even our youngest Patriots can be a part of our Yumtrepreneurs program, which invites them to design and run a food truck for a day, targeting the middle and upper school market. The Entrepreneurship Institute helps students see that they don’t need to wait. They can have an impact now. 

How does the IB program differentiate Carrollwood Day School in an increasingly competitive education landscape?

IB has always been ahead of the curve in truly preparing students for their futures. It is grounded in developing core competencies and skill sets that transcend disciplines. Students learn to be critical thinkers, communicators, and empathetic, kind people. Those skill sets help them whether they become neurologists, English teachers, or pursue something entirely different.

IB also includes rigorous course content that prepares students to step seamlessly into college. It gives students credit for not just being machines who memorize and repeat things, especially now that machines can do a lot of that. IB allows students to exercise their critical thinking and their ability to ask good questions and come up with innovative, unique answers earlier than in traditional structures.

I think IB has always distinguished us in that way, and as the world faces a moment of technological transformation, it is even clearer how future-proof IB is as an educational system. It develops core competencies that will never be irrelevant or outdated.

How are you attracting, developing, and retaining top teaching talent?

That is a core question we talk about all the time at the board and administrative levels. Our number one priority in our strategic plan is to attract and retain top talent.

Like any industry, we have to look at the emerging workforce. For education, the number of students completing education degrees has really fallen off, so it is harder to attract top people into education. What you offer as a school and as a workplace has to stand out.

We have developed a growth system for teachers where we truly invest in their ongoing professional development, increasing our professional development budget profoundly over the past five years. Teachers love to learn, so creating high-quality educational opportunities throughout their careers is important to us.

We have high expectations, but also a lot of support. To show our teachers how we value them, we have created step points where teachers can build portfolios to demonstrate mastery and become master teachers or mentor teachers. Teaching can be difficult because people become better and better, but there is not always a clear promotion path that allows you to stay in the classroom doing what you love, which is having an impact on kids. We wanted to create recognition and reward for increasing mastery throughout the length of a career.

As an IB World School, we also offer unique benefits, including an international teacher exchange. Teachers can visit schools around the world, learn from global educators, and pursue their own passions. We are always looking for ways to extend our mission to faculty and keep them engaged.

What are some of the most pressing challenges facing independent schools today?

Independent schools have to continually show their value proposition because families are investing a tremendous amount. That motivates us to be excellent.

Independent schools are also facing the same challenges educators face everywhere. The world is evolving rapidly, and it is our responsibility to ensure our curriculum and instructional methods are truly preparing students for the future.

Students are growing up in a complex world. They face many different pressures as developing young people, so we are constantly challenged to make sure none of them slip through the safety nets we create. We have to fully understand the student and adolescent experience from a social-emotional view and educational aspect. This allows us to create programs and opportunities that help them navigate childhood and adolescence well from all angles.

How do you engage with the community?

Our vision is to build a community prepared and inspired to better the world. It begins and ends with the connection of the people in our community. As an IB World School school, we have a place here for everybody. We come together with respect and around a shared purpose to prepare and inspire our children for the future.

One thing I love about the IB mission is the idea that people with their differences can also be right. To me, that means people with diverse viewpoints, backgrounds, and perspectives can sit together, talk about real things, disagree, and come out with better solutions because of that disagreement.

We are not here to make everyone think the same or be the same. We are here to appreciate each other in all of our differences so that together we create something unique. 

Our students are our best examples and ambassadors. Together they do extraordinary things. They are involved in community projects, state organizations, and volunteering. A group of our students in See US Now have written, advocated, and helped pass legislation on Capitol Hill protecting foster kids. Another group engages with Mort Elementary to offer consistent, high quality literacy support and mentorship. Another is working with the local school dsictrict to create a platform to help all students access high quality college guidance. They truly showhow CDS can have an impact on Tampa Bay, now and well into teh future, as our home-grown talent plants seeds here. 

Personally, I am also involved with the Tampa Bay Chamber’s Workforce Development Committee and the board of the Florida Council of Independent Schools. We are always looking for ways to showcase Carrollwood Day School as a resource for Tampa Bay, providing a globally minded, entrepreneurial education and our future community leaders.

What are your key goals and priorities for the next two to three years?

We are beginning our strategic planning process next year, and it is all about the school of the future. That means making sure we are the school of the future for educators and for students.

For educators, we want to be the destination school for exceptional teachers and be responsive to their lives and needs in a way that no other school is.

We want students to know we are at the top of our game, looking around the corner of the future, and truly preparing and inspiring them to be leaders in that future by providing a relevant education and unmatched opportunities.

It’s an exciting time to be in education, and the students are amazing. If anyone needs an optimistic boost, come to our school and see what these kids are doing every day in their classrooms, and you will know the future is bright.