HHS Welcomes New Principal Jeffrey DiLollo


Kristen Caruso

Principal JeffreyDiLollo talks with students during lunch.

Rebecca Ries, Editor-in-chief

With the start of the 2022-2023 school year comes new beginnings – and a new principal. Meet Jeffrey DiLollo, HHS’s newest leader. Coming from a background of vast experience: from history teacher to coach, and administrative positions, DiLollo now takes on the role of HHS Principal. His eagerness to meet everyone is already evident in just a few months on the new job.

Principal DiLollo served for a time as a high school teacher of history and social sciences, with a focus on psychology and 20th century American studies. He also has worked as a coordinator of many programs, such as special education, at-risk student support, athletics, clubs, and department leadership. Clearly, Mr. DiLollo has much experience from an array of areas.

He already has had the chance to interact with different groups of students and faculty alike, such as the robotics team and the Peer Mentoring program. He remarked how unique HHS is for a large school.

“One of the things that surprised me a bit is how there’s a family feel here, in even such a large school,” DiLollo said. “I don’t think everybody here notices that, but it’s a rare thing to have a school this size with this type of family feel and small community feel, which is great.” 

DiLollo has been impressed with HHS in other aspects too. He is excited about all of the programs offered, and is hoping to build on some of those groups as well. He appreciates that there are “plenty of great experiences and opportunities” in a school where people still support one another. 

There’s certainly been a lot of staff changes at Hillsborough within the last few years, and Principal DiLollo understood this from the start.

“I really think it’s important to not fit the school to the principal, but the principal fit to the school,” he said.

He’s eager to grow the HHS community, while still holding strong to past traditions and experiences at the school. 

DiLollo is excited to join the Hillsborough ranks, and his time here has already been full of meaningful connections and positive impressions.

“It has been such a breath of fresh air to start here with so many people, students and faculty alike, who are just eager for new people and new ideas, and really accepting and embracing, and I’ve just enjoyed every moment of it,” DiLollo said.