Making a Difference in Education: Jessica Wasilewski '98

Jessica Wasilewski ’98 always knew deep down she wanted to be a teacher. She sees joy in learning something new each day and is passionate about spending time with her students to help them grow, something she says her own teachers at Community School helped inspire.

“I can remember an important lesson I learned from every single teacher, coach, and advisor I had at Community School,” said Jessica, who skied cross country, played soccer, and served as Student Senate president her senior year. “They were people who made me feel confident and capable. They pushed me to be better. They were good listeners and made it clear that they were there not only there to help us succeed as students, but also thrive as human beings.”

After graduating, Jessica attended Middlebury College, where she earned bachelor degrees in economics and math. She honed her teaching skills as a student teacher through the school’s teacher education program, and, after graduating in 2002, landed her first job teaching high school math in Maine. Jessica headed back to school and earned her MS in Leadership from Northeastern University in 2007. After teaching at various day and boarding schools in Boston, she moved back to the Wood River Valley in 2011 to join Community School as its first Director of Residential Life for the brand new Residential Program.

“I had an amazing experience as Director of Residential Life at Community School,” she said. “It was fun and rewarding to be a part of something new at a place that did so much for me as a student. I learned a remarkable amount and got to work with some amazing students and colleagues. It was an important time in my career and my life, and it was a privilege to work there.” 

She remained at her alma mater for two years before she and husband David moved to New York, where she joined Manhattan’s Trinity School. She currently teaches upper school math and economics at Trinity, and, this fall, was appointed the Head of the Math Department.

“I think everyone who has made a career in education finds energy from working with students, but I think the single greatest thing I get out of teaching is that I honestly learn something new each day. I love how willing my students are to tinker with ideas, to make mistakes, and rework things. Class always ends too soon. The conversation between student and teacher is at the heart of Trinity’s mission, and we spend a lot of time working with our students one-on-one or in small groups outside of class. It is really fun to work with such engaged learners. This dialogue between faculty and student is something I valued when I was a student at Community School. I am certain that having teachers who really listened to me as a student helped influence my philosophy as an educator.”