Independent schools pour significant resources into their advancement playbook: giving days, traveling to meet with donors, and appeals. Yet the highest-leverage potential donors are often hiding in plain sight.
Consistent small donors, young alumni, or new grandparents might possess major gift capacity. The problem isn’t a lack of prospective donors; it’s not being able to identify them.
Windfall recently sat down with leaders from St. Andrew's Episcopal School, International School of Boston, and Avon Old Farms School to discuss 2026 development and advancement insights. The consensus was clear: finding the next major gift requires shifting from ad-hoc wealth screening to a continuous engine for discovery and prioritization. The panel discussed five key ways to leverage continuous intelligence to surface major gift prospects and fuel their advancement strategies:
- Boost Accuracy to Fuel the "Courage to Ask"
- Master the "Always-On" Seasonal Rhythm
- Shift from Static Audits to Continuous Discovery
- Maximize Travel Investments
- Screen the Full Ecosystem
1. Boost Accuracy to Fuel the "Courage to Ask"
Traditional bulk wealth screening often fills your CRM with static and stale data that is 50% inaccurate, according to a study by Deloitte. This lack of precision causes schools to miss high-capacity households entirely or waste time on the wrong prospects.
By using deterministic wealth and career insights for education, you find donors who can give at your top level. This provides the clarity to rank visits and the confidence to make seven-figure asks. When data is right, your team has the base to be bolder.
"When my gift officers see the number, they have more confidence going in and asking the big ask. They're not going and saying, 'Really? A million dollars? Are you sure?'... The biggest goal was just not under-asking anymore."
— Sarah Wallace, Director of Planned Giving and Research, Avon Old Farms School
2. Master the "Always-On" Seasonal Rhythm
A major gift is often missed because the appeal happened at the wrong time. In 2026, replace one-off audits with a year-round cadence that aligns with your school's natural cycle:
- Identify high-capacity families at the point of acceptance to pre-brief leadership for summer travel and fine-tune advisor pairings for day one.
- Spot triggers like liquidity events in real-time to catch donors at their peak moments of capability and readiness for a major gift.
- Start the cultivation process for managed portfolios on July 1st, moving past the old model of waiting for the first report card to initiate an ask.
"I screen as soon as we have next year's class in... I just find it helpful in the spring to have a sense of where we're headed and how we can be planful and mindful."
— Andrea Gosselin, International School of Boston
3. Shift from Static Audits to Continuous Discovery
Traditional bulk wealth screening is often a “one and done” project. The problem with this approach is that wealth is dynamic. Static audits anchor your strategy to the past with data that is often years out of date. Shifting to a continuous discovery engine replaces these historical snapshots with timely intelligence. To find “hidden gems,” you need a strategy built on the most current financial picture of your constituents.
"A lot of our data was very outdated when I came... it was really important for us to freshen that data up and be able to trust it, because that's ultimately really the most important thing." — Molly Laukes, Director of Development Operations and Research, St. Andrew's Episcopal School
4. Maximize Travel Investments
Travel is one of the highest expenses in advancement, yet trips are often built around habitual stops rather than current capacity. Before booking a flight to see a known advocate, use wealth data to identify donor clusters.
"If I know I'm going to Denver, I can just draw a little square [on the map], and everyone will pop up that's in your database in that area. If you see... a guy who's worth x, y, z money—hey, let's get some coffee."
— Sarah Wallace, Director of Planned Giving and Research, Avon Old Farms School
How much potential is sitting in the zip codes you already visit?
5. Screen the Full Ecosystem
“Always-on” screening isn’t just for current parents. The most significant "hidden gems" are often the institutional advocates you aren't currently screening. By examining extended networks, you identify high-capacity donors with a vested interest in the school.
According to the CASE Insights on Philanthropy in Independent Schools report, parents and grandparents of alumni have surpassed foundations as the leading source of support. By consistently screening, you can identify these families more quickly and engage them while their connection to the school is at its peak.
"We uncovered a family through Windfall... they made a significant gift that paid for the tool. Our CFO was very pleased with the immediate ROI."
— Andrea Gosselin, International School of Boston
→ See how one large public university leveraged Windfall to achieve an 11% increase in major gift prospects for their $1 Billion capital campaign.
Action Items for Major Gift Growth in 2026
- Stop the "One and Done" Mentality: Adopt a continuous screening schedule to catch wealth events (such as IPOs or business sales) as they happen.
- Measure Your Data Gap: Partner with Windfall to run a free Wealth Analytics Report on your records. You’ll get a full view of your database's wealth to uncover how much your current tools are missing.
- Prioritize the "Accepted" List: Screen new families right away. Use that data to architect a concierge-level experience before the first day of school.
- Expand Your Multigenerational Reach: Don’t stop at current parents. With grandparents playing an increasingly significant role–especially in elementary schools–ensure your screening process captures extended family networks to uncover hidden institutional advocates.
Ready to see how Windfall can surface the hidden gems in your own records? Request a complimentary Wealth Analytics Report to see exactly where your donor capacity is concentrated, and learn how to build a repeatable travel segmentation workflow your team can use year after year.
