Steering the Development Office from the Head of School Seat

I did not come to my headship as a fundraiser.

Like most heads of school, I came up through teaching, administration, and leadership roles that centered learning, people, and mission. Fundraising was part of the Head of School job description, but it was not the work that initially drew me to the role.

It did not take long to realize, however, that development would become one of the most consequential—and complex—dimensions of my headship. What surprised me most was not the asking. It was understanding who I was supposed to be in relation to the development office.

Being Both the Boss and the Team Member

As a senior administrator, I had interacted with development. I appreciated the work. But that experience did not prepare me for the reality of leading the function as head of school.

In development, the head occupies an unusual position. You are responsible for setting direction, allocating resources, and evaluating effectiveness—and at the same time, you are deeply dependent on advancement professionals who bring expertise you may not have. Development has its own rhythms, pressures, and methodologies. Understanding those realities takes humility and time.

I recently participated in a Blackbaud webinar with John Gabriel, president of Nerinx Hall High School, in which he shared his framing of the head of school/advancement director dynamic: “She works for me, but I work for her,” meaning his advancement director holds him accountable for donor outreach and he welcomes that.

The relationship must be powered by mutual accountability and shared ownership.

Julie Faulstich

To me, it is more of a partnership: the head of school and the advancement director co-create annual goals, drawing on data and each other’s perspective. But however you frame it, the relationship must be powered by mutual accountability and shared ownership. That means the head of school sets ambitious goals—and genuinely asks, “How can I help?”

The Head as Chief Relationship Manager

In conversations I’ve had with Hilary Wirtz, a deeply experienced development professional, she often describes the head as the “chief relationship manager and chief storyteller.” That framing resonates because it reflects what only the head can do.

Heads sit at the intersection of constituencies. Parents, alumni, trustees, donors, faculty, and students all experience the school through the head. The stories we tell, the way we listen, and how we show up in moments of joy and stress shape how people understand the institution.

John offered a compelling example of this. He shared that he personally calls every donor, including those making very small gifts. He personalizes tax letters. He writes to every student at the start of the year. None of this is about efficiency. It is about relationships. It communicates that philanthropy is not transactional—it is participatory.

Listening Before Leading

One of the hardest lessons for me was learning how little donor conversations are actually about me. Many donor meetings for which I carefully prepared ended up being almost entirely about where the donor was in their lives—what they were worried about, what they cared about, what was on their mind that day. I often shared only a fraction of what I had planned.

Those moments taught me that the work is not about delivering a polished pitch. It is about being present, curious, and responsive. Some of the most meaningful development moments of my headship came not from making an ask, but from creating space for connection.

Data as a Shared Language

Fundraising is deeply human work. But it is supported—or undermined—by systems.

Early on, I relied heavily on others to pull information for me and that dependence limited my effectiveness. Having real‑time access to development’s donor database changed how I showed up—at events, over meals, and in the unplanned moments that often matter most.

John echoed this, noting that he keeps his fundraising CRM open every time he makes a donor call. Knowing family context, giving history, and prior interactions allows him to approach conversations with continuity and respect.

Shared data creates a common language between the head’s office and the development office. It supports better judgment, clearer priorities, and more strategic use of time.

Strategy Over Habit

One of my ongoing concerns is how much money schools leave on the table—not because donors are unwilling, but because institutions rely on habit instead of strategy.

• Appeals sent at the same time each year because “that’s how we’ve always done it”
• Limited differentiation among donor segments
• Fundraising disconnected from the school’s most urgent priorities

At the same time, tuition sensitivity is real. Asking tuition-paying parents for more money without evaluating their capacity to give can damage the relationships you’re trying to nurture.

Philanthropy is not about extraction; it is about invitation.

People want to help deliver on mission when the need is clear. Campaigns grounded in data and realistic assessments of capacity can strengthen other forms of giving, including recurring donations and scholarship funds.

Trustees as Partners

No conversation about development is complete without addressing trustees. Boards must be more than passive recipients of fundraising reports. They must be active partners in the work. Hilary is clear on this point: trustees should have explicit philanthropic expectations articulated in a job description. They should understand the development strategy and how they can help advance it.

At their best, trustees extend the school’s relational reach. They serve as ambassadors who can speak credibly and confidently about why the institution is worthy of investment and introduce the school’s mission to new audiences. That role requires preparation and shared messaging—not assumption. Heads should be involved in crafting that message.

Staying in the Right Lane

Heads often ask how involved they should be in development work.

In my experience, the answer is deeply engaged—but not mired in the weeds. Heads need enough context and data to make strategic decisions and answer board‑level questions. At the same time, development directors need trust, autonomy, and respect for the complexity of their work.

As Hilary has said, the ideal head understands the depth of the operation, asks hard questions, partners thoughtfully—and then stays firmly in the role of chief fundraiser.

Why This Work Matters

Despite its challenges, development work offered some of the most unexpectedly meaningful moments of my headship. Sitting with donors, hearing their stories, and helping them connect their values to the life of a school put me in touch with the highest aspirations of an institution.

Fundraising is not a distraction from educational leadership. It is an extension of it.

The question for heads is not whether development belongs in the role—it does—but whether we are willing to approach it with the same intentionality, discipline, and humanity that we bring to every other dimension of school leadership.

That is work worth steering well.