Jesse McMillan
Principal, Westfield Middle School: Age 33
Jesse McMillan comes from a family of educators, and he counts himself lucky to have had teachers who made a big impact on his life — and inspired him to want to do the same.
So, it’s natural that he would find his way into that field.
But the path he’s taken has been anything but typical.
Indeed, he was named principal of New Hingham Regional Elementary School when he was just 24, making him the youngest principal in the Bay State at that time.
“I had people around me who really believed in me and gave me opportunities to grow; that made all the difference,” he said of his quick ascension to a top administrative role. “I loved being in the classroom, but I realized I wanted to have an impact beyond just my own students. Becoming a principal gave me the opportunity to support teachers and improve the experience for an entire building of kids at once.”
This mindset has propelled him to reach higher and seek new challenges, including his current position as principal of Westfield Middle School, where he leads a staff of 100 and provides direction and motivation to 700 students.
And as he goes about his work, he draws inspiration from his own middle school principal. “Every morning he’d greet me with ‘Hey, Jess!’ and it made me feel seen,” he recalled. “That stayed with me. It showed me the kind of impact a principal can have on a student.
“At the end of the day, it’s about people,” he went on. “If students feel safe and supported, and teachers feel valued, everything else starts to fall into place. That’s what I try to build every day.”
He said that he loves all aspects of this job, but especially the fact that no two days are the same, and every day provides a new opportunity for him to learn and build on those experiences.
“That process of continuous learning and refining my approach is what’s helped me grow as a leader,” he said. “And I hope it creates a culture where staff and students feel comfortable taking risks and learning from mistakes as well.”
“I have always seen myself as a learner first,” he continued, adding that this applies to everything from his teaching as an adjunct at Massachusetts College of Liberal Arts to learning something completely new like beekeeping. “It all comes back to that same curiosity. I think that mindset makes me a better educator and leader.”
It also makes him a 40 Under Forty honoree.
—George O’Brien
