Why Advancement Talent Is Hard to Find, and Where to Look Next
Listen on: Apple Podcasts - Spotify - YouTube
Heads across the country are noticing the same thing: it is getting harder to find strong advancement people. Jill Goodman of Jill Goodman Consulting returns to the podcast to help unpack why and what schools can do about it.
Jill has spent nearly 30 years in and around schools as a parent volunteer, trustee, and administrator before founding her consulting practice in 2017, and she now works with development offices and heads of school nationwide. Her starting point is honest and practical. Schools want deep experience from higher ed, nonprofits, or other independent schools. Still, the role at a small or mid-sized school is broader and less defined than at a traditional nonprofit, often a one- or two-person shop carrying a long list of assigned duties. Candidates who have specialized in one area, such as annual fund or alumni relations, can look at that scope and reasonably wonder whether it is realistic.
From there, Jill opens up the opportunity side of the picture. Schools offer real advantages, including tuition remission, a fundraising goal that is a modest share of the operating budget, and the daily lift of being around curious, healthy kids and teachers who care. She makes a strong case for nontraditional hires, describing the background and qualities she looks for, from corporate sales and entrepreneurial instincts to comfort around wealth and a healthy relationship with hearing no. She is equally clear about what success requires from the school: enough hours to do the job, a mentoring budget, a head comfortable in their fundraising role, and a board that understands advancement as a core part of the financial plan.
In the extended conversation for Moonshot Lab members, Jill lays out what a new advancement director should accomplish in years one, two, and three, and when fractional support makes sense.
Top 5 Takeaways
The small-school advancement role demands breadth, and that changes who will say yes.
A candidate coming from a large school or nonprofit has often specialized in one function. At a small school, one person handles everything from events to the database to major gifts, usually alongside duties outside development. Jill advises heads to name the real priorities clearly and offer support so the role reads as a focused opportunity rather than an open-ended list.Nontraditional candidates can be a strong source of advancement talent.
Jill looks for corporate sales experience, an entrepreneurial spirit, project management skills, tech fluency, and a genuine connection to the school as a parent, alum, or faculty member. She also looks for something harder to interview for: comfort with wealth and power, and a personality that makes people pick up the phone. Many of these qualities are easier to see in person than over Zoom.Hearing no is part of the work, and it is useful information.
Jill reframes rejection as feedback. A no might mean the ask came too early, the room was misread, or the gift needs to be shaped differently. People comfortable with that tend to grow quickly in the role, while those who fear it struggle to move relationships forward.Hiring a great person for too few hours sets everyone up to fall short.
Jill describes schools that hire for fifteen hours a week and then require five hours of internal meetings, leaving ten hours for an entire advancement program. Her point is that the board and head need to budget for the actual time the work requires, plus a year of mentoring, so a promising hire has a fair chance to succeed and stay.Advancement is a prong of the financial strategy, and the head is a key partner in it.
The largest gifts rarely move forward without the head’s involvement, because transformational donors want to hear the strategy from the person leading the school. Jill coaches some heads specifically on their fundraising role, and she encourages schools to treat development as a fully planned part of the financial model rather than an add-on.
