Most independent schools have offices of “advancement,” but what are they advancing, exactly? Broadly speaking, these teams help their institutions grow at steady, strategic, sustainable clips through fundraising and community engagement. But you can’t engage a community (at least, not well) without knowing it deeply. So who better to lead this team at Commonwealth than one of our own? 

Alisha Elliott ’01 was advancing Commonwealth’s mission well before it became her official job in 2017. (Keep reading for her surprisingly early fundraising work for the school.) As alums, Alisha and Head of School Jennifer Borman ’81 share an understanding of “the unique intensity and magic” of this place, Jennifer says, that other alums instantly recognize, too. 

Here, they discuss the critical gaps philanthropy fills at Commonwealth and how our approach to fundraising differs from most schools, what folks can look forward to during the school’s inaugural Alumni/ae Reunion Weekend, and how Mrs. Chatfield shaped giving over her tenure—and shapes it to this day.  

Alisha, what attracted you to advancement work and brought you back to Commonwealth in particular?

Alisha Elliott: It all started freshman year! My very first Project Week was interning on a gubernatorial campaign, and I just immediately fell in love with the energy and the passion of nonprofit work. The people I was working with were driven and creative, and that first experience really led me down a path to a career in fundraising. In fact, the first fundraising appeal I ever wrote was my senior year at Commonwealth to raise money for the yearbook. 

Before coming back to Commonwealth, I worked in fundraising for a handful of social-service and advocacy organizations [including Facing History and Ourselves, Horizons for Homeless Children, and the Anti-Defamation League]. I remember early on in my career, some of my friends would say things like, “So, you’re just asking people for money? I could never do that!” The reality is, the amount of time spent literally asking for money is quite small in fundraising; it’s about building relationships and trust and—most importantly, I think—listening. You connect people’s individual interests with opportunities to support the organization. 

As I was growing as a professional, my relationship with Commonwealth was also evolving. After graduating, I remained active as an alumna: I was part of the fiftieth-anniversary committee, and, later, I became president of the Alumni/ae Association. One of my favorite memories from that time was an event we did in 2013 called The Mermaid, which was modeled after [public radio’s] The Moth. It was a storytelling event, and I and another alum got to emcee. One of the stories that stuck with me was told by Polly Chatfield, who I know we’re honoring in this issue, where she talked about her experience attending a Von Trapp family wedding—which, as a musical theater nerd, was particularly exciting for me. 

When the opportunity came up to work in advancement at Commonwealth, it felt like such a natural pairing of something that meant so much to me personally and my professional experience. It seemed like it was meant to be. Being an alum myself, I could connect quite deeply with folks from the outset. 

I love that I get to interact with people at all different stages of their Commonwealth journey: I meet alums from the very early years, parents of alums, grandparents, current families. One of the things I’m really proud of about the way we do fundraising here is that we invite every family to have a face-to-face conversation with us in advancement—that’s something you won’t find in most independent schools. The conversations we have with new families are always enjoyable and a nice way to get to know folks. It’s also an opportunity for me and my team to talk about all the things the advancement office does besides fundraising, like family engagement. We talk about what it means to be part of the Commonwealth community and what makes it possible.

How does your shared background as Commonwealth alumnae impact your work?

Jennifer Borman: Oh, it is incredibly meaningful and organic. Between our time as students and working here, Alisha and I cover a lot of years in the school’s history. And when I talk to other alums, we have such an instant and resonant shared frame of reference: We sat in the same classrooms. We read the same poems. We admired the same teachers. We struggled in the same subjects. Nobody who hasn’t gone to Commonwealth truly understands the unique intensity and magic of this particular experience. I hear so much appreciation from alums for what this education allowed them to do with their lives, and I feel the same: a profound sense of gratitude for what I learned here and the doors I was able to open with what I learned here. It immediately creates shared common ground.

AE: I absolutely agree. We have the opportunity to meet formally and informally with alums throughout the course of the year, and I think we all recognize what is core to Commonwealth. Of course, over the past sixty-five years, the school has grown and changed, and that’s a positive. But, as alums, we also have a sense of what people don’t ever want to change. For example, when the last major capital campaign funded an elevator for the building, one of the first things we heard from alums was, “Oh, does that mean you don’t pass the clay anymore?” (Twice a year, the entire student body lines up around the staircase and passes 1,500 pounds of clay, in twenty-five-pound blocks, up to the fifth-floor ceramic studio.) Passing the Clay is a physical effort but it’s really a community effort, and the addition of the elevator did not change that. 

You’re planning to tap into that shared frame of reference at Commonwealth’s first-ever Alumni/ae Reunion Weekend this fall. Why the new format, and what can alums and their families expect from the event?

JB: We have had lots of ways of connecting with alums: traveling to cities where there’s a critical mass, having alums come to Commonwealth for various reunions. Some classes are motivated to organize their own events; other classes, less so. But I do think it’s been a bit episodic. Our goal for the Alumni/ae Reunion Weekend is to establish a regular cadence where any alum, no matter when they graduated, knows this will be an opportunity to come back to school, gather, and reconnect with former teachers and classmates. Another thing that will be particularly fantastic about this weekend—and I know this from having met so many alums from so many eras—is talking to not just your classmates but others from every decade of the school. Commonwealth alums are some of the most interesting and engaged humans around. They have had fascinating careers and really diverse experiences. It’ll be an added excitement to come back and meet new people. I think it’s going to be incredibly engaging.

AE: Absolutely. We want to make this a uniquely Commonwealth experience, and alums always want to learn and connect in very deep, authentic ways. We’ve had a few events over the years with masterclasses, and those have been popular, and so that is a big part of what this weekend is going to be—an opportunity to not just come back to Commonwealth but to be a Commonwealth student again for a day. We are going to have an impressive slate of classes taught by current and former teachers, as well as an alumni/ae version of City of Boston, which is a class that has existed for ninth graders since the early ’90s. There will be a number of other events, too, but our goal, really, is for it not to feel like just a weekend of receptions but a weekend with the Commonwealth community. (Turn to page 34 for more.)

Charles Merrill founded Commonwealth to make a premier private-school education accessible to the inner-city communities that had been denied it. Perhaps lesser known: he also was the school’s biggest benefactor for most of his life. What role does philanthropy play at Commonwealth today?

JB: I teach seniors, and we read sections of The Walled Garden, so I feel like I get a weekly dose of Charles Merrill’s vision through those conversations and that material. It was clear from the get-go that he wanted this school to be intellectually elite but not elitist. He intended, worked for, and funded students to attend who came from low-income and working-class backgrounds, and he was particularly concerned with access and opportunity for Black students, reflecting his long-standing civil-rights commitments. Those remain bedrock for Commonwealth. 

Mr. Merrill was also able to fund those commitments out of his personal fortune for the first twenty or so years of the school. Although he remained generous after he retired, we’ve had to become fiscally sustainable and fund those commitments through our community, not just through our inspiring founder. Each year, I work through a very complex budget that honors those commitments, and we could not do that without generous support from our community. Typically, about twenty percent of our operating budget comes from varying sources of philanthropy. Without it, our financial aid, our Dive In program, and many of the wonderful, distinctive features of a Commonwealth education, like Hancock, would be really compromised. Philanthropy is critical to what we do every day. And I am so grateful to have Alisha and her colleagues continue to find ways to inspire our community—and our community has really stepped up.

AE: I did not know Charles Merrill as a student, but when I talk to alums who did, so many talk about what they learned from him, particularly the responsibility to give back and to invest in the future of our students. Now, it is on us and our community to take on that mantle. 

Even in the last ten years, so much has been created out of whole cloth thanks to philanthropy. Dive In—which has grown to such a significant, incredible program—started in the summer of 2019 when a small group of people said, essentially, “We want to make this happen now.” And they gave to fund the entire first year of Dive In, because the school-year budget had already been finalized. Similarly, through the last campaign, the community came together and gave to create our very first physics lab. Again, it was not in the budget, but our alums and parents and parents of alums made that happen. 

More recently, we received generous donations to renovate the ceramics studio and to support professional development for teachers. These things are uniquely Commonwealth and, again, only happened because of philanthropy. Talking to people about those opportunities was such a joy and a perfect example of the importance of listening and connecting in fundraising. When alums say, “This particular teacher changed my life,” or “The trip to Italy really opened my eyes, and Commonwealth took me there,” we can show them giving opportunities that directly support our students having similar experiences today.

If someone is considering giving to Commonwealth, what do they need to know?

AE: If someone is considering giving to Commonwealth, that alone speaks to their commitment to the school, which is a gift in and of itself. So, thank you! 

JB: There are so many different ways to give, and we are so grateful for gifts at any scale. Some people think, “Well, $25 won’t matter.” It actually does. And we have donors who are getting to that phase of life where they’re thinking about their estate plans and what they might do to remember Commonwealth, again, at whatever scale is meaningful to them. As Alisha alluded to, that might look like a series of conversations to first find out what is in their heart: What do they care most about? And how do our priorities and their priorities map onto each other? They might give to fund students, say, going to Spain or having all of their textbooks and technology funded if they have a financial aid grant. 

We’re also really mindful of the need to fund our school into an indefinite number of tomorrows, and that means endowment giving is a priority for us. We were able to start our endowment thanks to Charles Merrill and have continued to nurture and grow it. Again, we engage donors in conversations to find out what matters most to them and share different ways they can make an impact, now or in the future. 

AE: You mentioned long-term planning, Jennifer, talking both about the endowment and what’s called “planned giving,” or people giving from their estate. We use the word “legacy” in both of those conversations. When we’re talking about planned giving, it’s the individual’s legacy; when we’re talking about the endowment, it’s the legacy of the school. Connecting community members with those opportunities can be really powerful. (Turn to the inside back cover for more.)

There are multiple efforts over the course of the year and opportunities for people to give in ways that feel good to them. That’s always important to us. Like you said, Jennifer, that varies greatly: it could be a gift of $25, or it could be five or six figures. But I appreciate that a significant portion of what we raise over the course of the year comes from gifts that are closer to $25. 

This issue of CM is dedicated to Polly Chatfield, legendary for her generosity with her time and expertise in the classroom, as well as for her philanthropic work at Commonwealth and at many other organizations. Can you tell us about her impact on advancement at Commonwealth—as a member of the team and to this day?

JB: When I think of Polly, I think of somebody who was generous to the core. And there were all kinds of ways that generosity showed up: the time and attention she would spend with individual students, the quality of her passion for teaching and advising, for scholarship, for embracing the life of the school. I feel like her generosity as a philanthropist was just part of a truly giving heart. She, I think, was particularly moved by students who might have had a harder time here, however that harder time could have been expressed. And she, like Charles Merrill, was particularly moved to ensure Commonwealth remained accessible to students from many different economic walks of life. Her generosity continued long after she left Commonwealth, and that was beautiful to see.

One of our most beloved giving opportunities is the Mary P. Chatfield Cultural Scholarship. This fund was established in the early 2000s by an alum who, as a student at Commonwealth, had traveled to Italy, and it was such a transformative experience for him, he wanted to ensure those experiences would be possible for our students for years to come. He was particularly close with and inspired by Mrs. Chatfield. And so this fund makes it possible for students to participate in our international trips regardless of their family’s financial capacity. The trips are a critical part of our language learning experience, and certainly, travel and particularly airfare have become exponentially more expensive. So this [Mary P. Chatfield Cultural] scholarship is particularly important and impactful.

AE: I completely agree, and I know she was still very involved after she had retired as a teacher but served as Chair of the Board in the ’90s. She was instrumental in launching more professional fundraising efforts at the school, and she was a generous and committed philanthropist throughout her life. She made connections, spoke with people, thanked people. That’s another wonderful and critical part of fundraising: saying thank you. And donors were always happy to get a phone call—or, more likely, a long-form, beautifully genuine, handwritten letter from Polly, signed “with love.” That’s how she did everything: with love.

This article was originally published in the summer 2026 edition of CM, Commonwealth's alumni/ae magazine.

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