Major Gifts and Digital Giving Experiences
Scaling Major Gifts. Strategies, action steps, and ideas for scaling major gifts by Tammy Zonker, Major Gift Expert & Keynote Speaker.
How Do Digital Experiences Shape Major Gift Decisions?
Your largest donors research you online long before a conversation and quietly between every conversation, so your website, giving flow, and donor portal are part of cultivation whether you treat them that way or not. The fix is straightforward: walk your own digital experience the way a major donor would, remove the friction you find, and start reading digital behavior as a relationship signal instead of a marketing metric. If you carry a major gift portfolio, this one is for you.
This is for major gift officers, development directors, and executive directors who want their digital presence to support high-touch relationships instead of quietly undermining them. After reading this, you'll be able to:
Audit your own giving experience the way your top donors experience it
Name the digital elements that matter most to six- and seven-figure donors
Spot major gift signals sitting in your website and email data right now
Let’s get into it
A few months ago, I sat with a board member who had given her organization six figures three years running. Warm relationship. Regular lunches. Everything you'd want.
Then she mentioned, almost in passing, that she'd tried to give online in December while traveling, gave up after the third screen, and mailed a check in January instead.
Nobody on the team knew. The gift came in, so the year looked fine. What the numbers didn't show was a loyal donor deciding, quietly, that giving here was harder than it needed to be.
That's the tension I keep running into in 2026. Major gift work is relational, and we're right to protect that. But we've let ourselves believe that because our top donors give through conversations, the digital side doesn't apply to them. It does. It just shows up differently.
Why do digital touchpoints matter to your largest donors?
Because your donors don't separate channels the way your org chart does.
The same person who has lunch with you also gets your email, forwards your annual report to her financial advisor, and looks you up on her phone in a waiting room. Every one of those moments tells her something about whether you're a serious organization.
Think of it as the lobby of your building. Digital rarely wins a major gift on its own. But it can cost you one, or plant a small doubt that shows up later as hesitation nobody can quite explain.
What makes a strong digital experience for a major donor?
Four things matter more than the rest.
A giving flow that respects their time. Test it on a phone. Count the screens. If a donor can't give a five-figure gift in under two minutes, or has to hunt for how to give stock or from a donor advised fund, you have a fixable problem.
Stock, DAF, and QCD options that are easy to find. This is where a growing share of major gifts come from now, and on most sites those options are buried three clicks deep under "Other Ways to Give."
Impact content with real substance. Your top donors want detail, not just emotion. A two-page outcomes summary they can send to a spouse or advisor is worth more than another photo carousel.
A portal that works, or none at all. A donor portal with stale data or a broken password reset is worse than no portal. If you offer one, someone has to own it.
And one more that gets overlooked: accessibility. Many of your largest donors are in their seventies and eighties. Small type, low contrast, and tiny tap targets are not a design preference issue. They're a revenue issue.
What digital signals point to major gift potential?
This is the part that gets fundraisers leaning forward, because the data usually already exists.
Watch for repeat visits to your ways-to-give or planned giving pages. Watch for someone downloading your financials or your strategic plan. Watch for a person who opens every email you send for six months but has never given above five hundred dollars.
None of those are proof. They're invitations to pay attention.
One approach I've seen work well is a simple monthly list: everyone who hit a high-value page more than twice, or downloaded a substantive document, cross-referenced against your database. Ten minutes of review, and you'll find two or three names worth a call.
Where does AI fit into this?
Right here. Ask an AI assistant to review your giving page from the perspective of a seventy-five year old donor considering a stock gift, and it will find friction you've stopped seeing. Ask it to summarize a month of web behavior into a short list of names worth reviewing, or to turn your outcomes report into a one-pager a donor could hand to an advisor.
What it can't do is tell you what that donor is ready for. That read still belongs to you.
How do you partner with marketing and IT?
Bring them a donor, not a complaint. Instead of "our giving page needs work," try "our top donor gave up on the mobile flow in December, here's a recording of me trying it." I've watched that reframe move projects stuck for two years. Then ask for one thing, not twelve.
Try this next week
Give to your own organization. Pull out your phone, make a real gift, and time it. Note every place you hesitate. This takes twelve minutes and changes conversations.
Find your DAF and stock path. Count the clicks from your homepage. If it's more than two, you have your first fix.
Pull one behavior list. Ask whoever owns your analytics for everyone who visited a giving or planned giving page more than twice last month. Look for names you know.
Want to take a deeper dive?
This week's episode of The Intentional Fundraiser Podcast, When Clicks Meet Conversations: Digital and Major Gifts, goes deeper on why advisors research you before your donor decides, and walks through the twenty-minute audit you can run this week.
I'd love to hear from you
When's the last time you gave to your own organization online? Connect with me on LinkedIn and tell me what you found. I read every note, and your answers shape what I cover next.
Your top fifty donors are already using your digital experience. The only question is whether it's helping you or quietly working against you. Pick one thing this week and fix it.
Frequently Asked Questions
Q1. Who is this approach best suited for?
This is designed for major gift officers, development directors, and executive directors who want to grow major gifts without losing donors to preventable friction. It works especially well if you already have a website with a giving page, an email program, and a defined group of top donors you're actively cultivating.
Q2. How much time should I expect this to take each week?
The initial digital audit takes about twenty to thirty minutes. After that, plan on thirty minutes a month to review digital behavior signals and one focused conversation a quarter with marketing. The consistency matters more than the depth.
Q3. What if my organization is small and I wear multiple hats?
The principles still apply, you just scale the tactics. Skip the portal conversation entirely and start with two things: make a gift on your own phone, and make your stock and donor advised fund instructions easy to find. Those two fixes cover most of the value for a small shop.
Q4. How do I know if it's working?
Look for early signals like fewer donors telling you they had trouble giving, more online gifts above one thousand dollars, and marketing bringing you behavior data without being asked. Over time, you should see faster gift processing, more stock and donor advised fund gifts, and fewer December surprises.
Q5. Where does AI fit into this, if at all?
AI is there to reduce friction, not replace your relationships. Use it to review your giving page for accessibility and clarity, summarize web behavior into a short review list, and turn long impact reports into donor-ready one-pagers. The work of reading readiness and building trust stays firmly in your hands.