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GEAR UP Alum Dylan Bertolini returns to VSAC as a counselor in the NEK

Written by
Dilys Pierson

June 23, 2021


dylan bertolini

For Dylan Bertolini, the decision to accept a job as a VSAC outreach counselor in the Northeast Kingdom this past February was more than just a career move. It was personal.

Dylan, who grew up in Danville, is driven by the opportunity to be involved with the community that raised him, in which, he says, “Kingdom kids” face a set of obstacles that their peers in Chittenden County don’t tend to share. Unfortunately, these challenges often play into their ability to pursue higher education.

“It’s not just poverty; poverty is everywhere,” says Dylan, who taught in Philadelphia before returning to Vermont last year. “But kids in the NEK are dealing with some extra roadblocks that might prevent them from experiencing an opportunity. For example, travel. You have a student who wants to go to the Governors’ Institute and can’t travel there. The lack of high-speed Internet is another example,” he says.
“Vermont is a really progressive place, and we have a ton of opportunities here,” Dylan says, making special mention of the dual enrollment program, as well as the new Green Mountain Grad scholarship, which allows any high school graduate of the Class of 2020 or 2021 to take one course free of charge at any of the Vermont State Colleges. (Learn more about the program at

“I want to make sure that students in the Kingdom have access to all of those things too,” Dylan says, by paying forward the many benefits he received from VSAC’s guidance, connections, and financial support when he was in high school.

Dylan’s parents, both successful business owners, did not go to college, though they emphasized the importance of postsecondary education for Dylan and his younger sister. “We were always told that college would be our ticket out,” he recalls. “And our parents were very encouraging and supportive, but they were also up-front about the fact that they didn’t have a lot of money to pay for it, so we’d better go out and get some scholarships,” he laughs. 

For Dylan, VSAC — and in particular, his VSAC outreach counselor, Marti Kingsley — helped connect him to the opportunities that would ignite his interest. 

“What I remember about my experience with VSAC was Marti Kingsley,” Dylan says, noting that she was the one who made possible one of his most significant high school experiences: attending the July Program at Bennington College. It was an incredible enrichment opportunity that his parents never could have paid for on their own, he says. 

“The whole month, I lived on campus, took college classes, and got to meet 250 kids from all over the country. It was awesome. It was also a real academic challenge,” he recalls, thinking in particular of the philosophy class he took that summer. “It was the first time in my life when I had to read something two, three times in order to understand it. But I was actually reading Kierkegaard in high school. VSAC provided that for me. They introduced me to the opportunity, and they paid for it.” 

When it came to deciding where to go to college, Marti also played a key role. 

“When I said I wanted to go to college out west and that I was interested in Arizona State University, Marti actually connected me to a friend of hers in Tempe who was an ASU alum. Somehow, I got a plane ticket out there, and that family hosted me for a week and gave me a personal tour of the campus.” Dylan ended up graduating from ASU in 2005 with a degree in history.  

After college, Dylan spent a few months working in Montana, then a few years working and traveling in Europe, before returning to Vermont to work in his father’s construction business. While Dylan enjoyed building houses alongside his dad, working outside in the winter eventually got to him, and he decided to go back to school at Lyndon State to earn his teaching certification.  

He then taught in Philadelphia for a time, before a conversation with an important mentor brought him back home. Once again, it was Marti Kingsley who suggested an opportunity she thought Dylan would love: working at VSAC. 

Dylan says that his eclectic life experiences have prepared him well for the role. 

“I can talk to students about a lot of different things they might be thinking about — whether it’s the typical Kingdom things of hunting and fishing, traveling the world, working in the trades, or going to college. But whatever they do, I want them to love it, and I want it to be a career, not just a job. That’s my main message,” he says. 

“Working at VSAC, I get to tell my story — talk about what worked, and what I would have done differently — so I can help others make good choices,” he says, and connect his students with opportunities in the same way that Marti did for him. 

“For instance, this spring I was working with a young woman who wanted to do a medical camp at George Mason University,” Dylan recalls. “Her family couldn’t pay for it, so I said, ‘Let me check with my boss.’ Turns out, VSAC was able to pay for half of the tuition, and she got her school and the local rotary to chip in the remaining amount, so she’s going. It’s that kind of stuff that makes me love what I do.”   

Need help with pursuing your career goals and education? VSAC is here to help you. For information on college and career planning and help with financial aid, go to and check out our online workshops and events. For an update of how we can help during COVID-19, click here. You can also give us a call at 800-642-3177, 8:00 am to 4:30 pm, Monday through Friday, or e-mail us at 

This story is produced by Vermont Student Assistance Corp., created by the Vermont Legislature in 1965 as a public nonprofit agency, to advocate for Vermont students and their families to ensure that they achieve their education goals. Our vision is to create opportunities for all Vermont students, but particularly for those—of any age—who believe that the doors to higher education are closed to them. We begin by helping families save for education with Vermont’s state-sponsored 529 savings program. To help Vermonters plan and pay for college or career training, our counselors work with students in nearly every Vermont middle school and high school, and again as adults. Our grant and scholarship programs attract national recognition, and our loan programs and loan forgiveness programs are saving Vermont families thousands of dollars in interest. For more about VSAC initiatives, go to

Need help with pursuing your career goals and education? VSAC is here to help you. For information on college and career planning and help with financial aid, go to and check out our online workshops and events. For an update of how we can help during COVID-19, click here. You can also give us a call at 800-642-3177, 8:00 am to 4:30 pm, Monday through Friday, or e-mail us at