Jack Chielli is a higher education professional who has spent the last two decades working across marketing, communications, and enrollment to help institutions grow, evolve, and—most importantly—connect with students in meaningful ways. Most recently, he served as the Vice President of Enrollment Management and Marketing & Communications at Mount St. Mary’s University.
Coming from a family of educators, Jack is well aware of how education can transform lives. Currently, Jack is exploring his next professional chapter and looking for a new challenge where he can continue to make an impact.
Extracurriculars
Jack loves to write poetry and has a master’s degree in creative writing. His poetry has been published multiple times in literary journals over the years. Recently, he learned that his poem “Spring Delivers Us” will be published in Keystone: Contemporary Poets on Pennsylvania, which is an anthology released by Penn State University Press.
Why we love Jack
Jack displays a strong dedication to his work and to the transformative effects it has on other people’s lives. With his penchant for creative and unconventional thinking, he has made unique impacts across three different careers within the institutions he’s worked for. With these qualities, he fits right into the Cowork Frederick community. Jack clearly has a passion for serving others in unique ways.
Q&A with Jack:
How did you get into a career in education?
I come from a family of educators, and their example shaped not only my values but also my career. I’ve seen firsthand how education can transform lives—open doors, shift perspectives, and create lasting opportunities for generations to come. That’s what drew me to this field and what has kept me committed to it for more than two decades. My time in education has centered around helping students find their path and thrive in higher education.
Cowork Frederick members tend to be a little unconventional. How does that apply to you?
That’s a pretty heavy question because everyone’s life is unique in every aspect, but from a professional viewpoint, I’d say this: I’ve had three very different careers—journalism, politics, and higher education—and in each one, I’ve tried to shake things up a bit. I’ve always been the person who looks at what’s not working and asks, “How can we do this better?” And I have not been afraid to take risks.
In government, I launched a public information office from scratch for an elected official. In higher ed, I restructured communications at two colleges and later unified four departments—marketing, communications, enrollment, and financial aid—under one strategic directive — to grow enrollment, which we did.
One of my favorite “rebel” moves? I was the first person in higher ed to put college recruitment ads on pizza boxes. It’s not as cheesy (lol) as it sounds. Students loved it—and so did the media. The story ended up in The New York Times, Fox News, NPR, and on the AP wire nationwide.
Who/What inspires you and keeps you going?
Family—and the desire to leave behind a respected legacy.
Which of the guiding values defined by Cowork Frederick members speaks to you?
They are all powerful values, and I think we adopt different ones at different times in life. Right now, I’d say it’s RESILIENCE. I wasn’t expecting to be job searching at this stage in life—and to be honest, it’s tough in this economy. But I’m not letting it define me or get me down. I’ll keep looking until I find the next right thing. This experience has humbled me and given me a new level of empathy and respect for what it’s like to be without work.
Any tips for others?
It’s all about relationships—and everything is political. Not political in the partisan sense, but in terms of navigating personalities, priorities, and institutional dynamics. Never underestimate the power of a positive attitude—or the damage that a negative one can cause.
Why Cowork Frederick?
One of the things I liked most about working was being around people and building relationships. I really missed that, so I joined Cowork Frederick. I still have a lot more Cowork folks to meet, but I like having a space outside my home office—and I love that it’s right downtown.
For those who want to learn more, how can you be reached?