Type: Webinar & Events

This piece is written by Suzzanne Eden, Partner with CCS Fundraising. CCS Fundraising is a strategic fundraising consulting firm that partners with nonprofits across sectors to design and implement fundraising programs that achieve transformational goals.

When most development professionals are asked about their endowment prospects, they describe the same person: a major donor, probably retired, likely already thinking about their estate, with significant wealth and a long history with the organization.

That search is happening at a meaningful moment. Total charitable giving reached a record $617 billion in 2025, and bequest giving grew nearly 20%, the strongest signal in years that donors are thinking seriously about legacy and permanence. The philanthropic conditions for endowment giving have rarely been better. The question is whether organizations are positioned to take advantage of them.

The problem with the traditional endowment prospect picture isn’t that it’s wrong, it’s that it’s incomplete, and that incompleteness is costing organizations real endowment gifts every year. Your strongest endowment prospects are almost certainly already in your database. They may not look like the profile above, but they share something more important than wealth: relationship depth, values alignment, and a genuine desire for lasting impact. The work of endowment fundraising isn’t finding a different kind of donor; it’s learning to see the donors you already have a little differently.

Watch the Webinar Replay:

Five Trends Shaping Endowment Fundraising Right Now

Understanding who gives to endowment and how to reach them, starts with understanding the environment they’re giving in. Five trends are defining this moment:

• Endowment fundraising is no longer niche. More nonprofits are actively starting or expanding endowment programs, driven by a desire to strengthen financial resilience and diversify revenue after COVID-era funding disruptions and continuing government cutbacks.
• Endowment giving is growing but remains concentrated. Endowment gifts are large in dollar impact but small in share of total giving, typically driven by major and planned gifts, which means the opportunity for organizations that invest in this area is significant.
• Donors expect clear, designated impact. Most endowment gifts are restricted by donors, often tied to specific purposes like scholarships, faculty chairs, or programs. This can limit institutional flexibility, but it also means that organizations that can intentionally offer specific funding opportunities of their choosing that are budget-relieving are better positioned to close, utilize, and steward, these gifts.
• Total giving tracks market performance with less volatility. The U.S. stock market has experienced a prolonged bull run with the S&P 500 over the past three years. Philanthropy tends to follow the market, though to a lower degree of volatility. Positive market growth suggests growth in giving.
• Planned giving and wealth transfer are supporting long-term growth. Bequest giving grew nearly 20% in 2025 (the largest single-source increase of the year) and the share of giving from bequests grew from 8% to 10%. Whether or not the Great Wealth Transfer has fully arrived, donors are clearly thinking about legacy.

Best Practice #1: Your Best Endowment Prospects Are Already in Your Database

Four donor profiles are worth knowing. The loyal annual donor, someone with five or more consecutive years of giving, is often the most overlooked endowment prospect precisely because they feel “already engaged.” But loyalty is one of the strongest predictors of endowment readiness, and that consistent giver deserves a closer look. The major gift partner is already investing at a significant level and looking for a way to deepen that commitment; naming opportunities tend to be a natural fit here. The values-aligned donor is motivated by a specific mission area or program and responds well to the question: “What does your gift make possible forever?” And the planned giving prospect may already be thinking about their estate, making endowment a natural bridge conversation, though it’s worth saying out loud that endowment isn’t only about planned gifts. Endowed gifts can be made now, named now, and felt now.

Across all four profiles, the signals look similar: tenure and consistency of giving, an expressed connection to a specific program or outcome, and life stage moments like retirement, an inheritance, or the sale of a business. If you’re not sure where to start, pull a list of everyone who has given for five or more consecutive years as a starting point.

Best Practice #2: Pipeline Management Doesn’t Require New Infrastructure

Knowing your profiles is step one. Moving donors toward a conversation is step two, and most organizations stall here, not because they lack the right donors but because they don’t have a structured way to prioritize and progress them.

When qualifying endowment prospects, think across three dimensions: affinity, access, and ability. Affinity is about relationship depth. Does this donor support your annual fund or express a personal connection to your work? Access is about entry points; are they an alum, a former board member, someone your leadership already knows? Ability is about feasibility, and this is where organizations cut their lists too early. A donor who can’t write a large check today might be able to make a multi-year pledge, give through a donor-advised fund, or designate a portion of their estate. Expanding your thinking about gift vehicles meaningfully expands your prospect pool.

The practical takeaway: add an “endowment readiness” flag to your existing prospect tracking and commit to moving those donors forward with intention: signal tracking, life stage moments, deeper engagement. No new infrastructure required, just a new lens. When donors feel uncertain about the present, conversations about permanence tend to land more naturally than they might in a stronger economic moment

Best Practice #3: Cultivation is What Moves Donors

The most effective endowment conversations happen long before the ask through cultivation experiences that make donors feel like partners in your mission rather than targets for it.

Consider two examples. An academic medical center wanted to endow a professorship in oncology research. Rather than opening with that conversation, the development team arranged a private meeting between a longtime major donor and the relevant faculty member about where the research was heading. They then invited the donor to a small advisory gathering where scientists were thinking through a new line of inquiry. The donor was asked for their perspective, not their money. By the time the endowed professorship conversation happened, it wasn’t really an ask. The donor already felt ownership over the work.

An independent school took a different approach. A twelve-year annual donor was introduced to an opportunity they didn’t know existed: the ability to endow an entire cohort of students. Before any ask, the development team invited them to a scholarship breakfast where they sat with three current scholarship recipients. The donor left saying “I want more of them to have this.” The endowment conversation followed within two months.

In both cases, the cultivation activity did the work, not the pitch. Your toolkit is probably already in front of you: faculty meetings, site visits, advisory gatherings. The shift is intentional: using those moments to help a specific donor see themselves in a specific opportunity before you ask them to fund it. That means matching donors to opportunities that genuinely fit, using their own language, and being direct that endowment and annual giving aren’t competing asks, they’re different expressions of the same relationship.

The Takeaway

Endowment fundraising isn’t a separate discipline that requires a different set of donors, a different pipeline, or a different kind of ask. It’s a deeper version of the conversation you’re already having grounded in relationship, activated through cultivation, and timed to when a donor is most ready to hear it.

In a year when bequest giving grew nearly 20% and the data signals that donors are thinking more seriously about legacy and the long term, that conversation has rarely felt more timely. The donors who will make your next endowment gift are almost certainly already in your database. The question is whether you’re creating the moments that help them see themselves in that opportunity before you ever ask.

Explore additional resources in the accompanying slide deck here.

This article is a companion piece to TIFF Investment Management’s Endowment Webinar Series, developed in partnership with CCS Fundraising. Watch Session 1, “Bringing Your Endowment to Life: How to Tell a Story That Resonates with Donors.”

The materials are being provided for informational purposes only and constitute neither an offer to sell nor a solicitation of an offer to buy securities. These materials also do not constitute an offer or advertisement of TIFF’s investment advisory services or investment, legal or tax advice. Opinions expressed herein are those of TIFF and are not a recommendation to buy or sell any securities.

These materials may contain forward-looking statements relating to future events. In some cases, you can identify forward-looking statements by terminology such as “may,” “will,” “should,” “expect,” “plan,” “intend,” “anticipate,” “believe,” “estimate,” “predict,” “potential,” or “continue,” the negative of such terms or other comparable terminology. Although TIFF believes the expectations reflected in the forward-looking statements are reasonable, future results cannot be guaranteed.

Originally presented as part of the TIFF Investment Management Endowment Webinar Series: “Bringing Your Endowment to Life: Three Best Practices to Engage and Inspire Donors.”

This piece is written by Suzzanne Eden, Partner with CCS Fundraising. CCS Fundraising is a strategic fundraising consulting firm that partners with nonprofits across sectors to design and implement fundraising programs that achieve transformational goals.

Many nonprofit leaders know their endowment matters. They can explain the draw rate, cite the fund balance, and articulate the long-term vision. And yet, when they talk to donors about endowment, something falls flat. The problem usually isn’t the endowment itself, it’s the story.

Most endowment communication is written for accountants, not donors. It leads with structure when donors are looking for something far simpler: proof that their gift will matter. TIFF Investment Management’s recent webinar with CCS Fundraising explored three best practices for making endowment communication more human, more compelling, and more effective.

Watch the Replay:

When Endowment Language Gets Stuck in Mechanics Mode

The most common failure in endowment communication is centering on the structure of the endowment rather than what it makes possible. “Our endowment has a current valuation of $25M and a 4.5% draw rate” is accurate, but not compelling. Compare it to: “Our endowment funded 32 scholarships last year.” Or: “Each year, I know that 20% of our operating expenses are covered. That’s the freedom that lets us take risks and serve our community in new ways.” It’s the same endowment, but a completely different story.

The question to ask before any endowment communication: What did our endowment make possible this year that wouldn’t have happened otherwise?

There’s also a question donors often have but rarely ask: why give to endowment instead of the annual fund? The short answer: endowment doesn’t compete with annual giving, it complements it. Endowment protects the organization’s ability to do the work the annual fund supports, year after year. When you can say that clearly and confidently, the conversation changes.

A Framework for Talking About What Endowment Does

When you’re not sure how to frame endowment for a particular audience, this structure works across sectors: endowment helps your organization a) serve more people, b) serve them better, and/or c) serve them for the long run. Endowment income expands capacity without relying on annual fundraising cycles. Financial stability enables excellence and innovation. And the endowment’s unique promise is continuity – not just this year, but every year. This framework works whether you’re writing a case for support, preparing for a donor conversation, or drafting a board update.

Making Endowment Tangible: The Power of Naming

Sometimes organizations feel hemmed in by a narrow view of naming and recognition options. The assumption is: “We don’t have a building to name. We’re not a university.” But naming can be applied to almost any endowment-supported function: a named position for a teaching artist, a fund supporting community health outreach, an endowed exhibition series, a scholarship bearing a family’s name. The key is to start with what your endowment actually funds and ask: what within that is nameable? What would a donor find meaningful to attach their name to?

Legacy societies are worth calling out specifically. They’re a way of naming the act of giving itself, creating a community of endowment donors that works especially well for organizations cultivating a culture of planned and endowment giving over time.

Where Endowment Should Show Up in Your Communications

The most common mistake organizations make is treating endowment as a specialized topic that lives only in planned giving materials or the annual report’s financial section. When endowment only shows up there, donors assume it is separate from the work they love. The goal isn’t to talk about endowment constantly, it is to make sure it shows up consistently in the places donors already pay attention: annual and impact reports, program materials, cases for support, board communications, donor letters, and your website’s impact or future vision sections.

Three Habits That Make Endowment Part of Your Everyday Story

You don’t need a new communications strategy, just three simple habits that require no budget, board approval, or communications overhaul.

Habit 1 – The Annual Snapshot: Once a year, share one image, one paragraph, and one outcome linked to your endowment. When donors come to expect it, they start looking for it, and when they start looking for it, they start thinking about it.

Habit 2 – Light, Recurring Mentions: One sentence in a leadership letter. A brief line in a board update. A closing thought in a stewardship email. These don’t need to be prominent; they just need to be consistent. Over time, they normalize endowment as a living, working part of the organization.

Habit 3 – One Story: Find one human story connected to your endowment and tell it consistently. A scholarship recipient, a staff position that exists because of an endowed gift, a program that survived a difficult year because of endowment income. If you can’t immediately name your endowment story, finding it is your most important first step.

The through-line: Endowment isn’t a specialized fundraising category; it is a story. When you center it in mission, make it tangible through naming, and weave it into everyday communications, it stops being something donors have to be “educated” about and starts being something they already understand and feel connected to. That’s when endowment giving becomes natural – not the result of a pitch, but the result of a relationship built over time.

Explore additional resources in the accompanying slide deck here.

This article is a companion piece to TIFF Investment Management’s Endowment Webinar Series, developed in partnership with CCS Fundraising. Session 2, “Who Gives to Endowment and Why: Donor Strategy for Lasting Impact,” takes place June 24. Register here.

The materials are being provided for informational purposes only and constitute neither an offer to sell nor a solicitation of an offer to buy securities. These materials also do not constitute an offer or advertisement of TIFF’s investment advisory services or investment, legal or tax advice. Opinions expressed herein are those of TIFF and are not a recommendation to buy or sell any securities.

These materials may contain forward-looking statements relating to future events. In some cases, you can identify forward-looking statements by terminology such as “may,” “will,” “should,” “expect,” “plan,” “intend,” “anticipate,” “believe,” “estimate,” “predict,” “potential,” or “continue,” the negative of such terms or other comparable terminology. Although TIFF believes the expectations reflected in the forward-looking statements are reasonable, future results cannot be guaranteed.

Artificial Intelligence (AI) is reshaping how nonprofits operate, communicate, and serve their communities. In this discussion, experts from The Do Good Institute at the University of Maryland and Compass Pro Bono joined TIFF Investment Management to share how organizations can approach AI adoption strategically, drawing from Compass Pro Bono’s own implementation journey — what worked, what didn’t, and what others can learn.

Watch the Replay:

Key Takeaways:

• AI can significantly increase nonprofit efficiency when adopted thoughtfully. AI is already embedded in many common tools, and when used intentionally, it can augment human work and free staff to focus more time on mission-driven activities.
• Building a responsible, intentional AI strategy is essential for success. Compass Pro Bono’s experience shows that clear policies, targeted use cases, staff training, and a culture of experimentation create the foundation for safe and effective integration.
• AI can meaningfully redirect staff capacity toward high-value work. Teams can reclaim several hours per week—sometimes 10–12—by automating routine tasks and enhancing critical thinking tasks, allowing more time for strategy, storytelling, and stakeholder engagement.

Explore additional resources in the slide deck here↗.

The materials are being provided for informational purposes only and constitute neither an offer to sell nor a solicitation of an offer to buy securities. These materials also do not constitute an offer or advertisement of TIFF’s investment advisory services or investment, legal or tax advice. Opinions expressed herein are those of TIFF and are not a recommendation to buy or sell any securities.

These materials may contain forward-looking statements relating to future events. In some cases, you can identify forward-looking statements by terminology such as “may,” “will,” “should,” “expect,” “plan,” “intend,” “anticipate,” “believe,” “estimate,” “predict,” “potential,” or “continue,” the negative of such terms or other comparable terminology. Although TIFF believes the expectations reflected in the forward-looking statements are reasonable, future results cannot be guaranteed.

TIFF held Impact Day on Tuesday, November 4, 2026, bringing our team together for a series of inspiring conversations with leaders across sectors — from technology and education to philanthropy and conservation. The day underscored TIFF’s commitment to learning from organizations driving meaningful change, deepening our understanding of the impact they aim to achieve, and exploring how we can translate those insights into our own work and communities. Here are some of the highlights from each of the day’s speakers.

Matt Gillin, Relay Network
Matt discussed his journey as an entrepreneur, from his family’s influence to founding two successful companies. He emphasized the importance of believing in your mission, staying agile, and harnessing artificial intelligence (AI) to amplify — not replace — human potential. Matt described AI as a platform shift unlike any we’ve seen before and reminded us that while the greatest risk may be not deploying AI fast enough, it’s ultimately human creativity and curiosity that move organizations forward.

Kerry Woodward, Philadelphia Financial Scholars
Kerry spoke about expanding access to personal finance education for Philadelphia students by equipping educators and bringing practical, classroom-ready resources to schools. She also highlighted the PFS Summer Experienceship, which provides students with real-world exposure, skill-building, and mentorship across local organizations, helping them grow financial confidence and envision pathways into future careers.

Keith Palmer, Travis Manion Foundation
Keith shared powerful lessons on leadership and teamwork drawn from his service in the Marine Corps and his work supporting veterans and families of the fallen and mentoring young people. He reminded us that effective leadership starts with “mission first, people always” — an understanding that you can’t accomplish the mission without investing in your people. Anchored in the Foundation’s guiding principle, “If Not Me, Then Who…,” Keith spoke about the importance of mentorship, community engagement, and collaboration as the true drivers of meaningful leadership and impact.

Oliver Bass, Natural Lands Trust
Oliver shared reflections from his 28-year career at Natural Lands Trust, highlighting how the organization’s endowment provides the financial stability needed to pursue mission-critical work — from protecting open spaces and managing development pressures to restoring wildlife habitats. He spoke about how the nature of conservation challenges has evolved, even as the organization’s purpose remains constant, and emphasized that strong financial partnerships make it possible to achieve long-term environmental impact.

A Commitment to Promoting Exchange

Impact Day is born out of one of TIFF’s most fundamental beliefs: that continual learning and open exchange strengthen how we serve our clients. By embracing broad perspectives, we challenge ourselves to think more creatively and to deepen our impact on the communities and missions we support. We’re grateful to each of the speakers for their insightful stories and contributions.

The materials are being provided for informational purposes only and constitute neither an offer to sell nor a solicitation of an offer to buy securities. These materials also do not constitute an offer or advertisement of TIFF’s investment advisory services or investment, legal or tax advice. Opinions expressed herein are those of TIFF and are not a recommendation to buy or sell any securities.

These materials may contain forward-looking statements relating to future events. In some cases, you can identify forward-looking statements by terminology such as “may,” “will,” “should,” “expect,” “plan,” “intend,” “anticipate,” “believe,” “estimate,” “predict,” “potential,” or “continue,” the negative of such terms or other comparable terminology. Although TIFF believes the expectations reflected in the forward-looking statements are reasonable, future results cannot be guaranteed.