While new Heads of School are often prepared for the academic and administrative aspects of the job, CCS has found that first-time heads are often surprised by the demands on their time posed by the school’s fundraising program. With ample time between appointment and the first day on the job, CCS has recommendations for how…

With increased enrollment challenges and constraints on tuition revenue, continued pressure to have competitive programs and facilities, and the growing need for endowment and financial aid, Heads of School are increasingly called upon to play an active role in securing philanthropic dollars. While new Heads of School are often prepared for the academic and administrative aspects of the job, CCS has found that first-time Heads are often surprised by the demands on their time posed by the school’s fundraising program.

With ample time between appointment and the first day on the job, CCS has recommendations for how new Heads can prepare themselves to be comfortable and confident in the role of “fundraiser-in-chief.”

Step 1: Foster a Culture of Philanthropy

A Head of School builds a culture of giving whether they realize it or not; each positive parent or alumni interaction, back-to-school night, soccer game, or science fair contributes to an invested and engaged community. As fundraiser-in-chief, a Head of School is responsible for the added work of articulating the need for continued support and making asks of the larger community.

The role of Head of School is an act of balancing both the internal and the external. Heads must manage internal priorities, including students, faculty, staff, finances, facilities, programs, DEI, and COVID-19 responses, along with external priorities, including communications, parents, and alumni. In addition to day-to-day administration, the Head serves as the voice and face of the school and its values. The Head is responsible for communicating the school’s vision and plan to all of the constituencies that make up an independent school community. While a Head’s time is limited and priorities are constantly shifting, fundraising touches almost every aspect of independent school life and merits dedicated time from the start to foster a strong culture of philanthropy.

Step 2: Chart Your Course

With many schools selecting new Heads a year in advance, newly appointed Heads have ample time to begin developing ideas for what they would like to accomplish during each year of their tenure. Any ideation around the big picture must also consider fundraising strategy, which can and should be different with each successive year of a Head’s time at a school.

To start, it is helpful to look at the first three years, the typical length of a new Head’s initial contract, to develop a better understanding of the types of fundraising activities a Head will participate in and the amount of time fundraising will require.

A Head’s first year should be spent getting to know the school community. Meetings with Board members, alumni, and parents will help a new Head gain a sense of where a school is and where it can go. These interactions will foster meaningful relationships with the school’s key stakeholders, which will lay a groundwork of trust that can only ease any future solicitations. A new Head will also need to rely heavily on the school’s advancement or development team to build a thorough understanding of fundraising development and culture. The development team will also play an integral role in helping a Head determine who to solicit and how to solicit them, in addition to arranging important cultivation and stewardship events that strengthen the school’s culture of philanthropy.

In our experience, a Head’s second year shifts away from year one’s focus on community building towards the development of a clear vision and strategy. A new Head will often begin a strategic planning or strategic initiatives process, during which he or she will work with their leadership team, the Board, and community committees to define and articulate a vision for the school’s future. This process should include a carefully coordinated fundraising plan to develop the resources that will likely be necessary to implement and to fund initiatives of the strategic plan. Many schools include fundraising considerations and encounter challenges when mapping their strategic plan to the fundraising potential after the fact.​ Getting ahead of the game and including fundraising from the start will smooth the transition from planning to implementation and execution. The time spent participating in fundraising activity will increase from year one, but the majority of time will likely be spent in stewardship and cultivation conversations, rather than direct solicitations.

For many Heads, year three will mean the preparatory and planning phase of a major gift campaign to resource the strategic plan. A Head of School may find that the community needs more time for feasibility and planning work to understand the donor base and capacity. This is also the time to define the specific case elements for the campaign. A Head will likely experience increased committee work and travel as he or she begins the important early work of securing leadership gifts toward the campaign goals.​ By the third year, particularly if the school is entering a campaign or major gift effort, a Head can expect that upwards of 50% of his or her time will be consumed by some type of fundraising activity, possibly more.

Step 3: Build Your Team

Though the Head of School is the fundraiser-in-chief, his or her responsibilities are too numerous and too demanding for all fundraising activity to fall on the Head’s plate. The Head is part of a larger fundraising team that includes the Board of Trustees and the development office. Each group plays a vital role in ensuring fundraising success at an independent school.

Ideally, every member of the Board will be a participant in the fundraising process, actively soliciting donors on behalf of the school. In reality, however, many Board members may not be comfortable asking for money. The good news is that there are numerous roles a Board can play to help advance the school’s fundraising initiatives. A Head of School can expect Board members to:

Many schools have a development or advancement committee which helps to create big-picture strategy around fundraising, is deeply involved in solicitation, and provides critical support to the school’s development team. Members of the development committee can act as a sounding board for the development team and provide feedback on what will resonate with the school community. They play a critical role in identifying prospects and encourage community-wide giving, strengthened by their own personally significant giving. Finally, they should work as ambassadors, warming up prospects for cultivation and solicitation, and thanking them for their support.

Just as a new Head will have expectations of the Board, so too will the Board have expectations for the Head and the development office. A Head should work closely with the development team to ensure that Board members feel well equipped to complete the fundraising tasks associated with their role. Development teams, in conjunction with the Head, should provide clearly defined responsibilities and expectations, along with short and long-term strategies and plans, access to fundraising training, and, most importantly, direct lines of communication. Board members are not just volunteers, but major stakeholders in an institution, and it is essential that they receive the resources they need to fundraise successfully.

Critical to the success of every school’s fundraising program is the development team. Members of the development team will provide essential support to the Head of School and the Board of trustees by setting strategy, preparing for and participating in solicitations, maintaining donor records, and often developing donor communications. The director of development should be a trusted partner to the Head of School, a skilled communicator who has a deep passion for the institution and its mission.

The director of development will need to be a strong manager, overseeing the fundraising staff, which should include frontline fundraisers (those who ask for money), and support staff (those who maintain the donor database, conduct research, and plan events). Though most of the development staff may not be in regular contact with the Head of School, they will need to advocate for the Head’s vision and earn donors’ trust. It is essential that this team receive the resources they need to do their jobs; a well-resourced development office will not only convey professionalism to donors but will also minimize staff turnover.

New Heads are often interested in their profession because of their passion to educate young people. Fundraising is the key that unlocks the school’s ability to provide an outstanding education, cutting-edge resources, a supportive community, and opportunities that transform students and the community at large. By fostering a community of philanthropy, charting your course, and building your team, a new Head can meet their philanthropic goals and exceed at delivering their mission.



Want to start a conversation?

We’d love to help you plan your next chapter!