RAISE Podcast: Kelly DeGregorio, Boston College High School

On this episode of the RAISE podcast, Brent chats with Kelly DeGregorio, Vice President of Institutional Advancement at Boston College High.

Check out this recap featuring our favorite takeaways from the episode, or listen yourself! 



Here are some highlights from the episode…

Kelly grew up in the Berkshires and attended Hamilton College. During her college experience, she lived abroad in Rome with Temple University. Fun fact: She DJ’ed throughout college as a side job. She launched her professional career in New York City working in children’s book publishing for William Morrow. 

Kelly’s first role in advancement was working for Scott Nichols in the annual fund at Harvard Law School. She credits this opportunity for teaching her what a high-functioning team looked like, and for giving her the opportunity to learn “how to do things the right way.”

Kelly spent over a decade at a community hospital system in Florida, where she learned how to be politely persistent. The outreach to a donor looks significantly different in a medical institution than at an educational institution. Often healthcare recipients are less interested in immediately engaging in a conversation about their experiences, though the impact of the institution is still a deeply valuable one. 

Early in her fundraising career, Kelly learned that the “right people need to be involved in every conversation”, and that’s not always apparent during the first conversation. She constantly asks her team, “Are you talking to the right person and not making assumptions about who has the influence to make a gift happen?”

Like many leaders, Kelly juggles her role as VP with her role as a fundraiser. She relies on her senior leadership team and uses tactics like biweekly standups to ensure she’s plugged into the needs of her team while on the road. For her, it is important to let “go of the idea of perfection as a manager and perfection as a fundraiser.”

Kelly believes that “if you get what you ask for, you didn’t ask for enough.” Often she’ll ask donors to tell her “about the impact you made with [a] gift” so she can understand what they expect to see from their philanthropy. 

During her time at Brigham and Women’s Hospital, which focuses on research, she learned to show donors the entire scope of a program so they can have a conversation about what impact they want to make with the institution. The hardest part of the job is getting numbers on the table without making it feel transactional. 

Kelly has moved between healthcare and academic fundraising throughout her career. She learned that she prioritizes community, presidential partnership, and institutional mission over the industry of the institution.

About Kelly… 

Kelly Degregorio, CFRE, is the Vice President of Institutional Advancement at Boston College High School. Kelly joined BC High in October 2018 following sixteen years building comprehensive healthcare philanthropy programs in healthcare. Prior to joining BC High, Kelly was Assistant VP, Major Gifts at Brigham and Women’s Hospital, where she led major and principal gifts initiatives for clinical and research programs including women’s health, cancer, newborn medicine, and obstetrics and gynecology during the hospital’s $1.5 billion Life Giving Breakthroughs campaign. Previously she had served as the Assistant Vice President at the Martin Health Foundation in Stuart, Florida, where she helped build a major gifts program that generated more than $115 million for the community hospital system. She has also held development roles at Goddard College and Harvard Law School, as well as marketing/communications roles in the media industry.

Kelly has presented on numerous fundraising topics at professional conferences, including serving as a faculty member at the Association for Healthcare Philanthropy’s Madison Institute. She is a graduate of Hamilton College.

Kelly lives in Milton with her husband Chris, son Will and two undisciplined dogs.

Boston College High is hiring! Want to work for Kelly? Connect with her on LinkedIn, and visit BC High’s website.  

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