In the public eye: Rossetti develops community leaders of tomorrow

Editor’s note: This is another in an ongoing series of Windham and Raymond town employee profiles.

By Ed Pierce

In a way, leadership is really about unlocking someone’s potential to become better, and that’s something Phil Rossetti practices every day at his workplace.

Phil Rossetti has worked as either a teacher, coach or
administrator at Windham High School for 26 years.
He is currently serving as an assistant principal and was
honored in 2002 as Maine's 'Assistant Principal of
the Year' and he was a finalist for the National
Assistant Principal of the Year. FILE PHOTO  

Rossetti has served as the Assistant Principal at Windham High School for the past seven years and has been associated with Windham High School as either a teacher or a school administrator for 26 years. His experience in teaching, coaching and leadership is exemplary and led to his recognition as 2022 Maine Assistant Principal of the Year and he was a finalist for the National Assistant Principal of the Year Award last spring.

“Our job encompasses many things but mainly working with students and staff to ensure all parties are able to teach and learn effectively,” Rossetti said. “The best thing about my job is helping students find success in school. Not everyone's journey is the same and school can be challenging for folks to navigate. Building relationships and developing trust with students, staff and families has allowed us to create an inclusive environment where people feel safe and able to take healthy risks.”

He grew up in Casco and graduated from Lake Region High School before earning a Bachelor of Science degree in Social Science Education from Plymouth State College in New Hampshire. Rossetti obtained a master’s degree in education leadership from St. Joseph’s College.

His first job in his educational career came as a Social Studies teacher at Windham High School in 1996. In 2015, he became the Assistant Principal of South Portland High School for a year before returning to Windham High School in 2016 and he continues to excel in that role as one of the school’s assistant principals. He’s also served as a football coach, girls’ basketball coach, and baseball coach.

According to Rossetti, the most challenging aspect of his work involves finding the support necessary to help students that are struggling socially, emotionally and with substances.

“There is a real lack of resources in our state, county and community for youth that need support,” he said.

From his perspective, Rossetti says some people think his position as a school administrator is all about one thing.

“The biggest misconception people may have about my work is all we do is discipline,” he said. “It is certainly a part of what we do, but it's a small percentage.”

In more than two decades of interacting with staff and students at Windham High School, Rossetti has accumulated many fond memories through the years, but several stand out over all the others.

“One that sticks out for me was winning the 2009 State championship in football. It was amazing to see all the neon shirts and most of the town of Windham on hand to watch the game, and it was truly a great moment for the community,” he said. “The other moment happens every June at graduation. The handshakes, hugs, tears, laughter, and Thank Yous as we celebrate each student’s journey to graduation is an incredible moment.”

The long hours at the school are worth it to Rossetti as he relishes his role in positively shaping community leaders for the future, and he says that his family understands how important his work as an educator is to him.

“They're proud of my dedication to the RSU, the students, and the staff I work alongside,” he said. “They like the schedule that allows us to still have quality family time during vacations and summer.”

Rossetti’s work with students doesn’t stop outside the front door to the school.

“I spend a lot of time working to include the community in our school and the school in our community,” he said. “I serve on the Board of Directors of Be the Influence; I am a member of the Third Thought Advisory board; I serve on the Substance Prevention Grant Committee for the Town of Windham; and I am an advocate locally, statewide and nationally for education supports as a former Maine Assistant Principal of the year and a National Finalist for Assistant Principal of the Year.”

He says the most important thing that he‘s learned while working for Windham High School is simple.

“RSU 14 works hard to support all students and seeks out multiple pathways for all students to find success,” Rossetti said. <