Ms. Caroline Reilly ’87, director of alumni and parent engagement, has been a cornerstone of the school community for over 15 years. She has played a pivotal role in developing the school’s extensive network of alumni and parents, which helps support the school’s daily operating expenses and long-term projects.
Ms. Reilly ensures that every five years alumni have the chance to revisit the school’s campus with former classmates. The Alumni and Development Office hosts reunions in both the fall and spring every year. This spring’s reunions will welcome alumni from class years ending in four and nine from as far back as the class of 1949 to the fifth-year reunion for the recent graduates of the class of 2019.
Ms. Reilly works closely with Mrs. Lisa Brown, chief of staff to the head of school, to plan special events for alumni. Mrs. Brown said, “Ms. Reilly is a valued colleague, friend, and advocate for all Bearcats. She remains cool under pressure, and she always brings camaraderie, collaboration, and calm to events in which she is involved. She is an integral member of the community, as she helps connect the past and the present by engaging with alumni. She has deep knowledge of people’s interests and accomplishments both on and off campus and is an invaluable resource to us all.”
Ms. Serena Oh Castellano, director of college counseling, is currently working with Ms. Reilly on the Alumni Outreach Committee for the celebration of the 50th anniversary of coeducation at the school, which will occur during the 2024-25 school year. Ms. Oh Castellano said, “Ms. Reilly embodies the ideal qualities of a strong leader. I can’t think of a better role model for the school’s students.”
The Alumni and Development Office stays busy year-round. It plans events years in advance and hosts many of them during breaks. Ms. Reilly said, “When I do get some time off, I spend it with my family. We love to go skiing; my sons are really great in terrain parks, so that’s always fun to watch. Going into their games and watching them compete is a joy.”
A crucial part of Ms. Reilly’s work is helping maintain and reestablish the relationships alumni formed as students. She said, “Part of the value of going to school at Hotchkiss is the network that you develop. After you graduate, you become part of this larger body of people spread all over the world doing incredible things. You won’t know how important the connections you made at Hotchkiss are until you’re a few years out. Staying connected to your Hotchkiss friends is really important, because those people will be your best friends for life, no matter where you are in the world.”
