Steven Bertozzi Named New Middle School Principal

When people learn that Steven Bertozzi is a middle school educator, their response — perhaps recalling their own experiences or the challenges of raising a child through the middle grades — often falls somewhere between awe and sympathy.

But for Steven, who became the principal of Milton’s Middle School in December, the magic and messiness of tween and early teen years affords an opportunity to support students as they navigate the important transition from childhood to young adulthood.

“I think one part of the challenge of being a middle school principal or teacher is that you just want everyone to know how amazing this age group is, how resilient they are, how curious they are,” he says. “The rest of the world doesn’t always see promise in this age group, so it’s our responsibility to continually remind kids how special they are when the rest of the world treats them like they’re not.”

Middle school is an exciting time for students to become more independent, discover their interests, and explore aspects of their identities. Steven’s dedication to middle school education comes from inspiring teachers who helped guide him through those years.

“They had such an impact on my life and took such an interest in me and my growth as a learner and as a person. I loved school growing up; it was a place where I could learn, play sports, do art, and just discover what I liked to do,” he says. “Middle school is about character, and as the adults in the community, we get to set the tone for who these young people are going to be.”

Steven began the 2019–2020 school year as interim principal, and strong support from students, faculty, and families soon made it clear he was the right person for the job, Head of School Todd B. Bland says.

“Steven is a dedicated educator who has proven to be an effective leader. His passion for teaching our Middle School students — helping them to grow intellectually, socially, and emotionally — shines in his work,” Todd says. “I am thrilled to work with Steven as he transitions to a role in which he can develop and implement a long-term vision for our Middle School.”

Steven has more than a decade of experience working at independent schools, including teaching and serving as a grade dean at Hawken School, in Lyndhurst, Ohio, and as a department chair at Hyde School in Woodstock, Connecticut. Prior to becoming principal, Steven was a Grade 7 social studies teacher and coach at Milton and a leader of student cultural clubs and affinity groups. He has also been a member of the Middle School’s leadership team for the Office of Multiculturalism and Community Development (OMCD), helping the division in its strategic diversity, equity, and inclusion (DEI) work.

DEI initiatives are central to Steven’s focus in the Middle School. He plans to expand faculty professional development and to work with the faculty and the OMCD to identify specific action steps going forward. He has been impressed with student leadership in DEI work: Students join and lead discussions about social identities like race, gender, and socioeconomic class, and the student diversity leadership group conducts workshops on important topics such as body image.

Additional priorities include strengthening the academic program with interdisciplinary and service-learning opportunities. “The students are recognizing the resources we have at our fingertips, both in the city of Boston and from families and community members,” he says. “It’s amazing how often our kids ask for community service work.”

Steven is also excited to continue working with the principals of the Upper and Lower Schools to align curriculum throughout the School. It’s important for students and teachers to thrive within their own divisions, but also to recognize that Milton is a K–12 community, he says.

What makes Milton’s Middle School such a special place is the level of support students receive from their teachers, advisors, coaches, and counselors.

“In all the different ways we interact with them, we know our kids well,” he says. “We take the time to meet with them, look at patterns, discuss their growth. We celebrate who they are beyond just learners. We celebrate their individuality and what they bring to our community. We celebrate leadership in all its forms in the Middle School. We see the value in the whole child.”


The curiosity to ask why and the courage to speak out are qualities that lead to innovation and change. The individuals featured in this issue embody these qualities. Through their questioning, leadership, and willingness to share their views, they are making a difference–in their professions and in the world.