Where AI Fits in the Major Gift Cycle

Fundraising moves when relationships move.
And relationships move when the friction falls away.

In this episode, we explore how AI can quietly support every stage of the major gift cycle without replacing the human heart of the work.

From prospect identification to stewardship, you’ll hear how practical AI workflows can reduce administrative drag so you can show up with donors more present, more prepared, and more confident.

We walk through the major gift cycle step by step and explore how AI can support:

• Prospect identification and portfolio prioritization
• Faster donor research and one-page briefings
• Turning messy post-visit voice notes into CRM-ready contact reports
• Stress-testing cultivation strategies and next steps
• Strengthening the systems that support real relationships

Along the way, I share a real example of narrowing a 150,000-person database to 300 high-potential prospects, and how today’s tools can compress months of manual work into something far more manageable.

The goal isn’t to automate fundraising.

The goal is to strengthen the systems that allow fundraisers to focus on what matters most: the relationships.

If you’re interested in going deeper, I’m developing a new program called The AI Advantage for Major Gifts, where we explore these workflows across the entire major gift cycle.

You can join the waitlist here:
letstalkfundraising.com/majorgifts

If this conversation resonates, share the episode with a colleague who lives in spreadsheets and leave a review to help other fundraisers find the show.

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Transcript

First Try With ChatGPT

Keith Greer 0:00

So let me tell you about the first time I opened ChatGPT. It was November of 2022. The tool had just launched publicly, and everywhere I looked, people were talking about this miracle new technology that could write anything for you. Essays, articles, emails, you name it. So of course I was curious. I opened it up and typed what was probably one of the worst prompts I've ever written in my entire life. I said something like, write an appeal letter for me. And what came back was not great. It was bland and generic and completely disconnected from any real organization or mission. At one point, it even dropped into this kind of Mad Lib style format where it said something like, insert organization name here and insert mission cause here. And I remember sitting there thinking, well, that's not going to help anybody raise any money. But instead of closing the tab, I got curious. What would happen if I gave it more information? So I started experimenting. I told it about the organization. I told it about the mission. I told it about the audience the letter was going to. I started shaping the tone and the message and the transformation that I wanted the reader to experience. And the results started getting better. Not perfect, but better. It became this interesting little experiment. But here's the thing. If my job at the time had been focused on writing appeal letters or grants, that might have been a real game changer. But that wasn't my job. My job was major gift fundraising. My work wasn't primarily about writing letters, it was about building relationships with donors, preparing for conversations, figuring out who I should be reaching out to in the first place, thinking strategically about how a relationship might move forward. So using ChatGPT to write appeal letters didn't really fit into my day-to-day workflow. And that's when the experiment changed. Instead of asking, can this tool write things for me? I started asking a different question. Where could this tool support the real work of major gift fundraising? So over the next couple of years, I started experimenting. Simple prompts, complex prompts, custom GPTs, little systems that could help with research, preparation, documentation, anything that might help me do my job a little bit better, a little bit faster, and a little bit more easily. And over time, something interesting started happening. These workflows were freeing up hours every week. Hours that I used to spend sitting behind my desk digging through data or trying to organize information. Hours that I could now spend doing the work I actually wanted to be doing, meeting with donors, preparing for conversations, thinking more clearly about the relationships that I was responsible for. And that's what eventually led to the idea I shared in last week's episode, a program I'm beginning to develop that I'm calling the AI Advantage for Major Gifts, where I'm exploring how these kinds of workflows might support the entire major gifts cycle. If you'd like to follow along as that idea develops, you can join the wait list at let's talkfundraising.com forward slash major gifts. I'll share updates there as the program takes shape. But today, I want to take a step back and look at a bigger question. Because after all of this experimentation, one thing became really clear to me. AI isn't just useful for one or two fundraising tasks. It can quietly support every stage of the major gift cycle. So today, I want to walk through that cycle with you and explore where AI might fit. Not as the strategy, but as a tool that helps the strategy run more smoothly. So let's talk fundraising. Major gift fundraising is a system. And if you've ever gone through the CFRE process, you know that system is based and rooted in best practices that have been developed over the last 30 or 40 years. They might go back even further than that, but it's really within that last time period that it's become systematized and routinized because fundraising runs on systems. I think before that, maybe people were doing major gift work kind of by the seat of their pants. They were figuring it out as they were going along. But now we have a structure that we're able to follow. We know where people are coming in at. We know the process to move them into qualification and into a nurture-cultivate relationship, all the way up to a major gift and stewarding that gift so well that they want to give us again and again and again. These systems help prevent us from reinventing the wheel every time we start on a major gift relationship. Because without systems, the knowledge that you develop over time lives within individuals. But these systems that have been developed, they allow our work to scale. They allow others to repeat what we've been able to achieve and accomplish ourselves. But these systems, they require processes because a system only works when a process exists. Without it, it's willy-nilly flying by the seat of your pants. And every fundraiser would be out there building their own version of what a major gift pipeline looks like. That leads to inconsistency. It means that we're going to have some organizations that do this work really well. We're going to have some people that really know how to do major gifts. And there's going to be a lot of people out there that are flailing and failing because they don't know what to do. And without systems, it slows down not just institutional learning, but our entire sector learning. We're starting to get better at doing major gifts. And without systems, we have inefficiency. We're not focusing where we need to be focused. We're not progressing relationships down the pipeline the way that they need to be processed. We're not making the asks when it's appropriate to be making the asks. So having a system in place it's not going to work in every situation, but it helps us get better in the long run. So if we're starting to look at the major gift life cycle, we, you know, we start at the prospect identification stage. Who in our orbit has the potential inclination and the potential capacity to become a major gift donor? Because we're not going to be spending months or years developing a relationship with somebody that either has no interest in what we're doing or does not have the capacity to give more than a couple dollars a month, maybe a couple dollars a year. Then we're going to move the people that do have that capacity and the inclination into a qualification stage where we're figuring out, are they actually interested? And is this something that they want to be a part of? And once we knew that, then we can start moving them into the cultivation phase. And this is where a lot of the work can get really messy, trying to figure out does this person know everything that they need to know to move just a little bit further in this cultivation stage? Are they getting close to us being able to make an ask just yet? Or do they still need some more work along the way? But as we kind of move through that, we start to build confidence in where this relationship is going. They build confidence that we're able to deliver on the work that we say we can. And then we get to that magical moment where sometimes we don't even have to make the ask because they say, I want to do this. How much does this cost? And that's an amazing feeling. And that's kind of where most of my biggest gifts have come from because that work has really led to them wanting to do this. It's no longer about me having to make the ask, although sometimes I do, but it really has helped them develop the inspiration and find a way to achieve that inspiration on their own through the work that we do within our organization. So we're at the ask phase. And they sign, say yes, and they sign off on the gift agreement and they transfer the money over to us. And it's a great day. It's super exciting. And then we have to move into the stewardship phase where we are delivering on the impact that their gift has made possible. And this is perhaps one of the most important steps because oftentimes people who are able to give those major gifts, they're not just giving it once. They're going to give it again and again and again. But not if they don't trust us based on that first gift that they gave. So we have to make sure that we're doing a really great job delivering on the impact that we promised. Because if we do that, they'll want to give to us again. But each one of these stages has its own administrative work that goes into it. And so it's so easy for us to be able to spend half or three quarters of our week stuck behind our desks, doing the administrative work that is absolutely important to major gift fundraising, but it's not the work that moves the relationship forward. It's not the work that brings the gift in the doors. But that administrative work does support the relationship. We just need to be able to close the amount of time that we're spending in the administrative work behind our desks in isolation without connection to other people. And that's where I've been able to leverage AI to be able to assist at every single stage of that work so that I can be out on the front lines, boots on the ground, doing the work that I not only love, but that moves the mission forward for the organization. And it's really important here to understand that AI is not the strategy. I am not an AI evangelist that says, let's use AI because it's AI and it's great. I am the kind of person that believes deeply in the established fundraising strategy that we have as a sector. And I've learned to leverage AI to support that work because AI is strengthening our processes. It's oiling those gears so that things move a little bit faster. They move a little bit easier. But it also helps us strengthen our processes so that we can support stronger relationships along the way. Technology here is becoming a quiet assistant. It's not becoming the relationship manager. So let's start at prospect identification because this is where all of the work really begins. And if you've been listening to the podcast for a while, or even just last week, you heard me tell the story about how I had a 150,000 member database with no prior major gift work done before. And we were going into our first capital campaign, and we had to figure out who from 150,000 members we were going to be talking to. And oh my God, it was terrifying. But over the course of about a month or two months, I was able to look at all of our data and start coming up strategy by strategy and step by step and refining and narrowing that enormous database down to 300 people that I thought would be our best potential prospects for major gifts for this campaign. And it worked because our goal was to raise$3 million in the next 18 months, which was enormous to come from an organization that was raising less than$200,000 a year before that. But we not only achieved the goal, we far surpassed it and raised$4.2 million in that short, narrow time period, with no major gift work having been done within the organization before. But if AI had been around in 2012 when I was doing that work, I probably could have had it done within a week instead of having it take me two months to go through all of that data. Because I had to build that algorithm manually. I had to validate it every step of the way, make sure that I was not getting too narrow or too wide with the filtering and the scoring and the weighting that I was doing. But the model was absolutely successful. But AI is able to get there much faster than I was able to get there. Because AI is a phenomenal pattern recognition tool. Like if I still had access to that database, I would love to just upload the whole thing, you know, clean so that we're not putting in any uh personally identifiable information into it, but cleaned and uploaded into that and see what it would say are the best potential prospects that I should be looking out for. And AI is really great with more data. It's actually easier for it to do its job. If you have a database of 100 people, you might get some help, but it's probably not going to be a lot of help. So when you're looking at your data set as part of your prospect identification pipeline, you're probably gonna want to have at least a minimum of 4,000 records, 4,000 potential prospects for AI to be looking at. And AI can identify trends that humans might miss. So while we might easily work with something like a recency frequency monetary model, RFM, AI might start looking at micro trends, who's opening emails, who's responding to emails, who is making different moves on data that we're collecting that I can't even think of. And it's tying all of those patterns together and says, this is the next person you should be looking at. And that's huge because it reduces the manual data work that we have to do looking through those huge databases. But it's really important that as fundraisers, we're still interpreting those results. We're still reviewing what it's coming back and telling us, and that we're asking along the way, why do you think this person is the next person I should be reaching out to? And you can absolutely build your own models within Chat GPT or whatever AI tool you're using, because you can define who your ideal donor profile is, and that's probably a really great place to start. But if you have no clue what you're doing or where to begin, you can turn a little bit of that over to AI and ask it to help you structure a model that makes sense, review what it's telling you it's gonna do before you allow it to go unchecked. But there's no technical expertise that is required to review this data now. You're now somebody that is focused on what is the logic of this system? How is this being used? How is it being interpreted? But you're not having to learn how to use SQL, you're not having to learn how to use all of these other technical languages that I have no clue what they even are. But AI is able to take your guidance, to take your logic, and it's able to execute the analysis seamlessly. It can also help with research and visit preparation. When I was getting ready to do major gift fundraising with somebody that I'd never met before, and I'm going into that qualification and that discovery visit, I'm spending hours scrolling through LinkedIn, trying to find out what's their job, what's the organization that they work on, what are the things that they're posting and do they care about this work that we do in any kind of a way? What voices are they following? Then I'd look at what is out there on the internet. Are they serving on any boards? Are they listed there? So all kinds of information that I'm trying to pull in from lots of different places. And it would take me, you know, at least an hour, usually two or three, to get through all of that. But with a very simple prompt, you can turn that over to Chat GPT, and in one minute, two minutes, maybe three at the most, it's able to scour most of the internet and come back with some really amazing results. And then, magically, almost it can turn it into a really quick one-page bio on that person so that you are ready to start having some conversations with them. The other part that I've discovered is that fundraisers want practical AI applications. There's a lot of folks that are out there that are talking about the strategy, but they're not turning it into implementation or execution. And so fundraisers are feeling unsure what AI could actually help with. There is curiosity here because they're intrigued, but there's a lot of caution because, especially early on, there were a lot of these AI models that didn't have great safety protocols in place. And that's gotten better, but it's still really important to use these tools judiciously to make sure that you're not uploading personally identifiable information about your donors, to make sure that what you're giving AI is something that you'd be comfortable going out potentially to the entire world. Not because AI is taking our data if we're on certain models anymore, but because there are data breaches. And I mean, it's not exclusive to AI that this can happen. It can happen within our own organizations. But there's a really deep appetite for learning how to utilize these tools in a practical, grounded way that understands the fundraising profession. And that's where I want to really keep this work that I'm doing grounded. Because whatever we use AI for in our major gift work, we have to make sure that the processes stay human and relationship-centered. We have to make sure that we are being ethically responsible in the way that we're using this information and the way that we're leveraging data. Because AI can draft information, but it's really important that as fundraisers, as people with judgment, we are confirming its accuracy, that we are staying human and in the best interest of everybody involved as we go forward, because trust is so vital to our sector. And if we lose that trust along the way, it doesn't just damage our organization, but it starts to damage everybody that works within philanthropy. The other part that I really like to use AI is within our contact reports and the CRM memory. Because documenting the gifts and the conversations that we're having along the way is the institutional memory beyond what my brain is able to remember, beyond what the donor is able to remember. Because if either one of those goes, I mean, my memory is not perfect at all. But if I'm able to document in the moment, I can return back to the knowledge that I had and use it in the future. By documenting it in our CRM, the relationship extends beyond individuals. Because if I win the lottery and I don't have to work anymore, the person following in and after me, they know exactly where this relationship is at and how to move it forward. Our CRMs are there to preserve continuity of the relationship between the donor and the organization and the teams that we have rely on that shared information. So documentation supports that major gift strategy. And there's some traditional challenges within this documentation, because oftentimes our contact reports are delayed. Maybe we're getting to them at the end of the day, maybe the end of the week. Some of us I know even get to them at the end of the month. And by then our memories are really kind of fuzzy on what did we actually talk about and what actually happened. We have notes scattered in our iPhones, we have them on pieces of paper, we have them on sticky notes that might be posted to our desks. And so it's not consistently in one place. Writing it down takes time, the consistency varies, and in the messiness of it all, the information gets lost. But one of the things I was super excited about creating was a custom GPT that I can turn to as soon as I get to my car after a donor visit. I'll sit there in the parking lot or in the driveway, and I will just pop into voice mode in that custom GPT and just do the ugliest of brain dumps that you can possibly imagine. Everything that happened, everything I can think of. And AI can take that nonsense almost and it can analyze it and put it into a beautifully structured summary that standardizes our reports so that we are consistent across the entire database. And if you're working as part of a large team, everybody's putting in a contact report that looks similar, so that our prospect research teams behind the scenes, they have consistent reports that they can look at instead of having, you know, things that say like, I had lunch with a donor. Great, what did you talk about? Or almost equally as frustrating is when somebody puts in a 15-page recap of every single thing that happened, including all of the stuff that's completely irrelevant. But AI is able to determine what the relevance of that brain dump was. And that improves our collaboration across the systems. And that helps us have better strategy and portfolio thinking. Because the strategy here remains human. The major gift strategy requires judgment. And right now, artificial intelligence is okay at judgment. It can help nudge us in the right direction. It could potentially put up like those bumpers that we have at the bowling alley that prevent us from getting gutter balls. But it's not going to make sure that we get a strike every time. Fundraisers are the ones that are able to interpret those relationships because the context matters deeply. And a lot of this relies on intuition. And that's something that AI doesn't have, at least not yet. But that is something that humans are really great at. And this relationship guides the decisions. So I like to leverage AI as a thinking partner. It can assist me with brainstorming, it can reflect my ideas back to me. It can suggest alternatives. So I like to leverage it as part of cultivating ideas on what are the next things I should do with this person. What are the next steps that I should be taking here? What are the things that they need to know that we haven't talked about yet? And it can start looking through our portfolios and identifying patterns of where we've been and start looking at who is ready to take those next steps and move into the ask. But it can also provide alternative perspectives to the way that we might be thinking. So AI supports the strategic thinking that we're doing by helping us get clarity around our decision making because it can organize that information in a way that supports the strategy. It helps us get to preparation much faster. It increases our insights in the work that we're doing. It reduces the administrative areas that we're focused on. Because who wants to be stuck at their desk for 40 hours a week? I mean, maybe an accountant, they like that. But I like working with people. I like being out on the front lines. And so it can help us think more clearly and the donor relationships improve when we're able to have those human connections. And so why does AI matter in all of this? Because it's helping us remove the friction in the system, the part that we don't really actually like to be doing. Because the administrative work it slows major gift fundraising processes and results. It's a great system for the time that it was developed in. But AI strengthens these systems, it greases the wheels, it reduces friction. And that allows fundraisers to regain time, to be more strategic, to have more visits, to build deeper, meaningful relationships. And I think that helps the work become more sustainable too. Because more presence with donors means that we're shifting our time from administrative work toward relationship building. Fundraisers are able to prepare for those visits more thoughtfully. Our conversations with donors get deeper and the strategy improves and our impact increases over time. So I want to be real clear here because AI supports fundraising. It supports the human work that we're doing. AI is not the replacement for the relationship. Because the relationship is the central part of everything that we are doing. And technology should serve people, not us serving technology. And our mission remains the focus of the work that we're doing every single day. If there's one idea I hope you carry with you from this conversation, it's this AI doesn't change the strategy of major gift fundraising, but it can strengthen the systems that allow that strategy to work. Because when you step back and look at the major gift cycle, every stage of it depends on processes. Prospect identification, research, visit preparation, documentation, stewardship. None of those pieces are the relationship itself, but they're the scaffolding that supports the relationship. And when those systems are slow or fragmented or overly manual, something important happens. The administrative work quietly begins to crowd out the relational work. But when those systems are clear and supported, something shifts. You spend less time managing information and more time preparing thoughtfully for the people that you're serving. You're walking into conversations more present, more prepared, and more confident about where that relationship might go. And that's really what all of this experimentation with AI has been about for me. Not automating fundraising to get rid of my work, not replacing the human side of the work, but supporting the work that makes those relationships possible. And that's the idea that eventually grew into the program that I mentioned earlier, the AI Advantage for Major Gifts. It's something I'm beginning to develop to explore those workflows in a deeper and more structured way across the entire major gift cycle. And just as important, it's being built by a fundraiser for fundraisers. This isn't coming from a Silicon Valley developer who has never sat in on a donor meeting, and it's not someone guessing about how fundraising works. It's coming from someone who has spent more than 15 years in this profession. I have my CFRE and I understand the pressures and the responsibilities that come with this work. So if this conversation sparked some ideas for you, I would love to invite you to join the waitlist while the program is taking shape. You can do that at letstalkfundraising.com forward slash major gifts. I'll also make sure to put the link in the show notes. The people who join this list will be the very first to hear when the program opens, and the first group of founding members are gonna have an opportunity to help shape the final structure of the course itself. Because the goal here isn't just to build another training program. The goal is to help fundraisers reclaim their time and their energy so that you can focus on the part of this work that matters most, the relationships. And if you've ever felt like the administrative side of this profession was quietly pulling you away from the people that you're trying to serve, you're not alone. But there is a better way to structure our work, one that gives donors the best of us, not what's left of us. So, thank you again for being here. I am so grateful that you're part of this conversation. And as always, let's keep talking fundraising. I'll see you next week, my friend.