The success of independent school fundraising hinges critically on the involvement of the head of school. For advancement directors, the HOS is not just your ally but a vital partner, wielding a unique influence that can turn a good fundraising campaign into a great one. 

While not every HOS has a natural knack for—or interest in—fundraising, they often possess an abundance of talent and skill that can be leveraged into effective fundraising strategies. As an advancement leader, you play a significant role in this process. Your influence can guide their inherent abilities and establish internal mechanisms of support. 

In this blog, we’ll explore ways to develop HOSs into masterful fundraisers, harnessing their strengths and aligning them with your school’s philanthropic goals.

The Fundraising Responsibilities of the Head of School 

A successful head of school is impressively multifaceted, embracing roles that span academics, administration, fundraising, community engagement, and strategic planning. As the face of the institution, the HOS must skillfully navigate these fundamental responsibilities to secure the financial future of the school: 

1. Lead vision and strategy. When they step into their role, heads of school also take the position of “fundraiser-in-chief.” It’s their job to identify new opportunities and craft clear, compelling strategies. The board and community will have input, but it’s the HOS that carries the weight of publicizing and implementing the vision.
2. Cultivate donor relationships and stewardship. Successful fundraising relies on efforts to nurture relationships with donors and build trust. While many fundraising transactions are handled by other advancement team members, donors appreciate hearing from the head of school. Especially with major-gift donors, the head of school’s efforts to understand their interests and align those with the school’s needs go a long way to reinforce long-term trust and support.
3. Build strong alumni connections. By leveraging the enthusiasm and relationships of alumni, the head of school can seamlessly integrate this community into the school’s culture of philanthropy. Alumni seek and value authentic and passionate leadership, a clear and compelling vision for the school’s mission, and a representative who is both accessible and engaged. Through these actions, an effective head of school can transform mere association into genuine partnerships. 
4. Articulate the school’s case for support. As the CEO of a school, the HOS must have an intimate understanding of the school’s financial picture. Ideally, HOSs can transform this fiscal data into a compelling story that makes the impact and needs of the school both tangible and relatable. In nearly every interaction and across all communication materials, the HOS must articulate a clear and convincing case for why the school is a worthy investment.   

Fundraising Challenges for the Head of School

Besides having a lot on their plates, most up-and-coming administrators aren’t exposed to fundraising until they become a head of school. That can be a scary proposition at first. In fact, according to a 2021 NAIS study, just 40 percent of sitting heads and 19 percent of aspiring heads feel prepared to fundraise. Let’s address this and other common challenges:

1. Time constraints. Dedicating adequate time to fundraising can become a significant challenge. It’s a delicate balance, where the HOS must make judicious decisions on how to invest limited time to nurture potential donors without compromising other vital aspects of the head role.
2. Limited experience or training in fundraising. The shift from being primarily an educational leader to a “fundraiser-in-chief” can be daunting. Lack of training or experience in this domain requires the HOS to embark on a learning curve, often seeking mentorship, attending training sessions, or learning from failures and successes.
3. Aligning fundraising goals with educational mission and vision. The HOS must continually assess how fundraising initiatives contribute to educational goals, ensuring that the pursuit of financial support does not detract from or distort the institution’s guiding principles.
4. Navigating donor expectations and balancing constituent interests. Balancing various constituent interests, including those of parents, alumni, and staff, adds a layer of complexity that must be delicately managed. The HOS must harmonize diverse interests while keeping the school’s overarching goals in sight.

Tailoring Strategies of Success for New and Established Heads of School 

While the fundraising challenges faced by the head of school may seem daunting, they are not insurmountable. The key lies in recognizing the unique position of the HOSs and then tailoring strategies to support and enhance their fundraising efforts. Whether you’re working with a new head of school adapting to the role or an established leader aiming to refine his or her approach, the following strategies will make you an influential partner.  

Build a Cohesive Internal Team

In many cases, independent-school leadership models rely far too heavily on the head of school. This has proven to be an unsustainable strategy, causing fatigue and attrition in this critical position. 

Schools must foster a culture where all revenue influencers—the business, advancement, and enrollment departments—are involved in analyzing trends and data, setting goals, and working together to maximize opportunities and growth. This not only makes each department more effective, but it helps create a more efficient model that promotes sustainability in leadership roles.

 

Chart a Shared Course of Action

We’ve established that the HOS cannot be present at every event or meeting. Therefore, a rigorous examination of your school’s leadership or cabinet structure is necessary. Ask the following questions:

• Is the HOS empowered to be as focused on donors as needed?
• Are we using the HOS’s presence to most effectively enhance fundraising efforts?

Collaboration is key. Your leaders in advancement and alumni relations must work closely with the HOS to scrutinize the calendar of annual events and stewardship efforts. Together, determine which are most crucial for the HOS to attend, taking into consideration the school’s goals and the head’s unique value in fundraising. Confidently delegate anything outside of this essential list to other capable team members.

 

Create Supportive Systems for New Heads of School

The announcement and arrival of a new HOS is a substantial opportunity to rally key leadership, the Board, and administration to generate excitement and nurture key donor relationships. 

If needed, it’s also a time to reset the alliance between a head of school and its development program. Here are a few approaches to establishing a beneficial partnership:

• Work together with communications, development, and alumni to strategically roll out the new HOS to the community. The more touch points there are early on, the more confident people will be—and the easier fundraising will become. 
• Coordinate special events and fundraising appeals that piggyback on the excitement. Make sure HOSs are familiar with any appeals that go out in their name.
• It can take a few years for new HOSs to feel completely confident in their knowledge of their community members. Have team members create donor profiles that provide a cheat sheet of family names and notable details on major-gift donors. Additionally, provide HOSs with a list of the top five to eight people they need to connect with at major events.   
• Don’t skip name tags at events while the HOS is getting acclimated. Make them even more worthwhile by adding notes like “alumni,” “parent,” or even listing their students’ names.   
  
   

Leverage the Experience of Established Heads of School 

Established heads of school typically feel more confident in the academic leadership and business aspects of their role. Often, this allows them to make connections with parents, alumni, and community leaders with greater ease. 

In your role as advancement leader, you can work closely with an established HOS to cultivate deeper donor connections and strategies. You can also let the HOS know about career-development opportunities in fundraising. 

Take, for example, these two highly recommended opportunities:

• Fundraising for Heads of School 2023
• CASE-NAIS Independent Schools Conference 2023