What If Major Gift Fundraisers Had More Time for Donors?

Most of us came into this work to build relationships. But too often our days get buried under contact reports, prospect research, and messy systems that keep us tied to a desk.

In this episode, we explore a simple idea: what if AI could handle some of the repetitive administrative work so fundraisers could focus more energy on donor relationships?

You’ll hear the story behind a set of practical AI workflows that began as small experiments and grew into a framework that supports the entire major gift cycle, from prospect identification and donor research to cultivation strategy, proposal writing, and stewardship.

Along the way we talk about:

• the hidden cost of administrative work in major gift fundraising
• how broken systems once kept me behind a desk nearly full-time
• the breakthrough that helped identify the top 300 prospects for a record-setting campaign
• how fundraisers are using AI to produce cleaner CRM records and better donor briefings
• ethical guardrails, data security, and keeping humans firmly in charge

This conversation also introduces a new program I’m developing called The AI Advantage for Major Gifts, built by a career fundraiser to help peers reclaim time and strengthen donor relationships with practical AI workflows.

If this idea resonates with you, you can join the waitlist here:
letstalkfundraising.com/majorgifts

💡 Want to take the next small step?

→ Free Download: 12 Fundraising Prompts You'll Actually Use

→ Course:  The Fundraiser's AI Starter Suite

Transcript

The Big Idea: AI As Support

Keith Greer 0:00

So I've had an idea. Since ChatGPT first became publicly available back in November of 2022, I've been experimenting with how AI might fit into the daily work of fundraising. Not as a replacement for relationships, but as a tool that could quietly take some of the administrative weight off of our desks. What started as a few small workflows, things like organizing donor research or drafting contact reports, gradually grew into something much more powerful. Systems that helped me spend less time managing information and more time preparing for real conversations with donors. Last summer, I ran a pilot program with a group of major gift fundraisers to see if those same workflows would work for other people too. And they did. And after following up with several of the people who went through that program, something became really clear. There's an opportunity here for fundraisers to reclaim a significant amount of time and energy from the administrative side of our work and redirect it back to where it belongs with our donors. So today, I want to share the idea that has been growing out of those conversations. And if you'd like to follow along as this develops, you can join the wait list at let's talkfundraising.com forward slash major gifts. That's where I'll share updates as this program takes shape. Because at the end of the day, major gift fundraising isn't about technology, it's about relationships. And the question I keep coming back to is this What if technology could help us spend more time where fundraising actually happens? Across the table from a donor. So let's talk fundraising. There's the tension that major gift officers or major gift fundraisers often feel. We know where we should be spending our time with our donors. Building relationships is central to that job. You don't get major gifts out of thin air. They don't just drop out of the sky. It takes time to build those relationships, to build trust, to build a sense of inviting people into the work and making them see a worthwhile investment in a change in the world that they want to see. But many of our days are dominated by administrative work. We're entering contact reports. We're scouring our databases for who the next potential major gift prospect is. We're doing a lot of work that isn't actually connecting us to our donors. And it creates a quiet frustration that many of us feel because a lot of us working in major gift work, we love working with people. It's what lights us up, it's what gives us joy. And when we're stuck behind the desk and we're stuck in a database, it can make that meaningful work feel so distant. It's something that we don't really recognize. And it's why many of us didn't get into this profession to begin with. We got in it because we wanted to make a difference. We wanted to show people that their investment in the work of our mission, of our organizations, something that oftentimes resonates with us personally, is something that they can get involved in too. And that doesn't happen when we're staring at spreadsheets or we're scouring through a database or we're stuck on LinkedIn trying to research who our potential prospects are. And so I want to share a story about a time from very early in my career when I was working across multiple databases and multiple spreadsheets. We were not a great funded organization. We were a million dollars in debt and we were really struggling to get going. And so the databases that we had, they were the cheapest databases out there. And we were actually running from two of them because one database just wasn't enough, I guess. And so we were having to manage multiple lists, multiple databases, and not even those could capture all the information that we needed to be able to run our operations. So we had multiple spreadsheets to start tracking all of that too. And it was a constant effort, juggling to keep all of that information organized, to keep the playbill listing that listed all of our donors and their giving levels correct so that we knew who was giving at what level, when their time to renew was coming in, and how they actually wanted their name to appear. And for a long time, we got it wrong just because there wasn't good systems. And what did that mean for my work in fundraising? It meant I spent probably 38 hours out of my 40-hour work week stuck at my desk. I wasn't out there building relationships. I wasn't doing the work that was keeping us afloat and helping us close that million-dollar budget shortfall. We were really struggling and it was hard. And I think that's something that a lot of fundraisers experience as well. And it wasn't until I went into a better-funded organization. They were still very new to major gift fundraising. They didn't have any systems in place, but they had a budget to be able to buy a great CRM system. And so we spent a couple of months building that out and cleaning up all of our data. But then we had 150,000 members in our database. And I was like, oh my God, where do I even begin with this? It's absolutely an impossible task. I didn't know what to do, where to go. And so I had to go back to the drawing board. And we had this Excel database with everybody, their giving history, their volunteer history, their professional information because we were a professional membership organization. And I built this wildly complicated Excel formula that looked at all the information we had on everybody. And over the course of a month or two, I was able to refine that algorithm in Excel. That was tough. But I was able to refine it. And it led us to our top 300 potential prospects that we should be focusing on. And it was amazing because we were headed into the organization's first capital campaign. They'd been around for 30 years, but we're only bringing in about$200,000 a year up until that point. So there wasn't any major gift work that had been really going on. It was a donation,$5 donation with your dues checkoff that was bringing in the money and a raffle that we were doing once a year. But there wasn't the major gift strategy in place. But now we at least knew who to focus on as we were headed into this$3 million campaign. And we had a very short time period to actually operate it because we were celebrating the grand opening of our brand new museum and our new building. And so we had about 18 months between that opening and the hundredth anniversary of the professional membership organization. So in 18 months, we had to raise$3 million from a plan that we had never done before. But because we knew who to talk to from our database, we were able to not only reach that$3 million goal, but we exceeded it and raised$4.2 million. And this was from an organization that had never done major gift work before. Like we were building these systems on the fly. And it was amazing. And it was so rewarding to be able to see that transformation within our organizations. But then ChatGPT came out, November of 2022. And I was like, I need to test this out because I love how technology can support our work as fundraisers and what we're doing. And so I've spent, what is it, three and a half years now figuring out how to use Chat GPT? How does it support the work that we're doing? Because when we have bad systems, there's of course a loss of efficiency. But the real loss is the time that we're spending with our donors. The real loss is the money that we're not bringing in to support our organizations. Because the administrative work, it crowds out that relationship work that we need to do so that we can actually raise money to meet our mission. And that tension eventually pushed me to start experimenting within ChatGPT. Where can I close the gaps? Where can I tighten my processes? Where can I build better systems that support my work of being out in front of those donors? And those experiments led to something unexpected. And that's when I created this pilot program. And what I wanted to do was do an experiment. Were these systems and processes within AI that I was starting to develop for myself, are they something that people in other organizations would be able to use too? Is it something that would resonate with them? Is it something that they would find value in? Or was it just because I loved technology that I made it work? But the thing is, I found that these test workflows that I had built for myself, they worked for other people too. They helped create practical AI-enabled systems that helped and supported fundraisers to go out into the world and do the work of fundraising, to build relationships better, to build them faster, and to build them stronger. And so the pilot program last summer, it was a test. It was absolutely not a polished course. Like there were lots of missing pieces within it, but the pieces that were delivered, people loved and they found value in them. People quickly understood what the practical benefits of having an AI-supported system enabled them to do in their fundraising work. Those workflows resonated immediately for the participants. And then they began adapting these ideas that I was developing into their own systems because there are hundreds of CRM systems out there, and there's thousands of implementations for every CRM system. So every organization is going to be unique in the way that they're adopting these tools. But having this framework to see how AI can support your work, it helped people in every situation that they were in. And the conversations they expanded beyond the original lessons and curiosity about additional possibilities grew. And then I had an even bigger realization. The program revealed to me that there is an entire major gift cycle that AI workflows could support. They could help take over some of the administrative tasks, but they could also help us prepare for conversations more deeply. They could help us go everywhere from prospect identification to visit strategy to moves management to practicing and rehearsing a major gift ask. And then once the gift was received, it could help us move into stewardship. And that insight, it planted the seed for this new idea. Because I started having conversations after the pilot program. I was following up with the people who went through it last summer. Now that it's been six or seven months since they went through it, they've had a chance to do real-world testing of the systems that I showed them and the systems that they built. And I wanted their honest feedback. And I was like, what stuck with you? What actually worked? And people were blown away with how good their contact reports and their CRM databases were getting. And that's where the relationship work lives long term. Because of course it's in our heads in the moment that we're fundraising and we're building these relationships. But what happens if something happens to the donor and they can't meet with us for six, 12, 18 months? What if we leave the organizations because we have won the lottery and we no longer have to work? The relationship information, if it's not there in the CRM, it's lost to the sands of time. But having great CRM contact reports was one of the standout things for everybody. And it helped standardize them, especially across large institutions, because now there was a system that was taking these wild brain dumps that people were sitting in their cars in their parking lots after a donor visit, and they were just spewing everything into these custom GPTs that we built. And it formatted it beautifully so that the prospect research team behind the scenes could go through and say, here's some next steps that you should be considering with this donor. Or if you're a small shop, it at least lets you know where you need to go when you have that next visit with somebody because everything is recorded so perfectly. But I also heard a lot of patterns throughout this. Fundraisers wanted to have practical AI applications. They wanted to know what else could AI help with. And there's a curiosity there that's also mixed with caution because a lot of people are concerned about the data security, especially when AI first came out, there were not a lot of precautions or safety mechanisms built into these platforms. It was give us everything and we're going to use everything to train the next model. And thank goodness there were fundraisers showing up at AFP conferences, giving feedback to those AI systems, saying, we don't want this if it can't protect our donor data, because our institutions, our sector is built on trust. And without having that trust in our systems, in our data security, in our safety, in the way that our teams are using these tools ethically, it doesn't work for us. But that appetite for deeper learning is real. And there's a lot of people out there that are teaching strategy. They're saying AI can do this, AI can do that, but they're not turning it into practical ways that fundraisers, boots on the ground, can learn and implement for themselves. Because fundraising is ultimately going to be a relationship-based profession. And so we have to make sure that any AI, any technology that we implement is going to be rooted and grounded in fundraising best practices. And so these conversations help shape my thinking. This pilot program that we did last summer, it could be something bigger. It could be a program that covers the entire major gift cycle, but it's something that's built specifically for people who are doing major gift work. And it's built collaboratively within the profession by somebody who is actually a professional fundraiser. I've been doing this work for over 15 years. So I know this work inside and out, backwards and forwards, upside down, standing on my head. I understand it. This is my job. And so I started developing the philosophy behind what I want this program to look like because AI is not the strategy. We don't need to change our fundraising strategy as our work evolves. Major gift fundraising is gonna remain relational. Technology should support that strategy, not replace it. AI is a tool that we can leverage to remove the friction, get us out from behind our desks, and having those face-to-face on the phone calls, over video chats, conversations with our donors. And the important part is that fundraisers have to remain central to everything that goes out the door. We're the ones that are remaining responsible for the judgment. We are the ones that are remaining responsible for the strategy. That all still lives in the very human work, in the human relationships that we do. AI is just the support system. Because AI cannot build relationships. Relationships require human presence. But AI can help us prepare the groundwork. AI can organize the information after a visit. AI can help us draft proposals or donor profiles that we're giving to our leadership team. But the relationship has to remain with the fundraiser. And so I think a lot of people in the sector, there's a fear out there. There's fear that AI is going to replace us. And I don't think that's true. I don't think that's even remotely on the cards yet. Because fundraising is fundamentally human. I think there are some people out there that want to have relationships with robots, but the vast majority of people don't. We want to be connected to each other, to another human, to our neighbors, to our best friends. Empathy and trust is what is at the center of what cannot be automated by AI. But these tools, they can change our professional effectiveness. Fundraisers who use AI are going to gain capacity. They're going to gain clarity. They're going to gain efficacy to be able to do their job better than fundraisers who don't. So the profession is going to evolve as these tools mature. And I want the fundraisers that I work with, the people in my network, I want them to be the best that they can possibly be. So I want to share what I see as the future. I see a profession where a major gift officer is preparing for a donor visit. And rather than spending two or three hours scouring through LinkedIn, scouring the internet for the person's profession and what organization they're working for and what boards they're serving on, they do a simple prompt into Chat GPT asking it to do all of that search and it comes back with the information in less than a minute. And all the information it gathers, it then puts it into a donor briefing so that the gift officer can go in and have that discovery visit with the donor already knowing a little bit about them. And it didn't take them two or three hours to do that work. They were able to get it done in less than five minutes. And so if you multiply that out over the course of a week, and maybe you're having five to 10 visits with donors a week, what if you could up that to 15, 20, 25? That kind of scale is exponentially valuable for your organization because the more people that we're able to bring into our circles, the more people that we're able to build and manage those relationships with and help them move through the pipeline from identification and not really knowing much about our work or feeling invested in it, all the way to somebody who's ready to give that major gift and make a transformation within the sector that they're interested in, mind blowing. It's about reducing the administrative part of our job so that we can focus on the relational part of our job. Because if we're able to have a really coherent database, if we're able to have everything systematized and routinized, then we're able to focus more on the strategy. We're able to focus on the human part of our work. We're able to focus on the parts that are gonna move the pieces forward. But we have to keep a program like this grounded in real work, the work that fundraisers do. So we want less time buried in our systems. We want to increase the time that we're being thoughtful. We want to have more energy headed into our donor conversations. And we want to have more clarity about the strategy for the portfolio that we're managing. And ultimately, all of it leads to more presence in our mission work. So let me bring this back to the idea that I shared at the beginning. Over the past couple of years, I've been experimenting with how AI might support the real work of fundraising, not replace it, not automate the relationships, but support the work that makes those relationships possible. Last summer's pilot program showed me something important. When fundraisers have practical systems that help with research, preparation, and documentation, something shifts. They get their time back, time to think more strategically about their portfolios, time to prepare more thoughtfully for donor conversations. And most importantly, time to actually sit down with the people who care about the missions that we're serving. And that's the idea that I've been working on expanding. So I'm starting to develop this program called the AI Advantage for Major Gifts. And this isn't a course about technology for technology's sake, it's about practical workflows that support the entire major gift cycle, from prospect identification and research all the way through cultivation, solicitation, and stewardship. And just as important, this program is being built by a fundraiser for fundraisers. It's not by a Silicon Valley developer who has never sat in a donor meeting. It's not being done by someone who is guessing about how fundraising works. And it's not being done by somebody who just started using Chat GPT last week. But it is being done by someone who has spent more than 15 years in this profession, who has their CFRE, who has walked through the same pressures that you feel, and who believes deeply in the relational nature of this work. And that's why I'm inviting you into this process so early. Because if this idea resonates with you, I really want you to join the wait list. And you can do that at letstalkfundraising.com forward slash major gifts. I'll also post a link to it in the show notes. The people who join that wait list are going to be the very first to hear when the program opens, and the first group of these founding members, they're going to be able to help shape the final structure of the course itself. Because the goal here is not 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 actually matters the most, the relationships. And if you've ever felt like the administrative side of this profession was quietly pulling you away from the people you're trying to serve, you are so not alone. But I do believe there's a better way to structure our work. One that gives donors the best of us, not what's left of us. So, thank you for spending this time with me today. I am so grateful that you're here, and I'm excited to see where this idea leads. And as always, let's keep talking fundraising. I'll see you next week, my friends.