The Donor-Driven Playbook: Engagement, Qualification, and Stewardship Done Right

Heart without execution remains aspirational …

… and systems without heart won’t scale

In Part 2 of this two-episode series, John Kundtz sits down with Greg Warner, CEO & Founder of MarketSmart, to discuss bridging “Start with the Heart” from philosophy into an operating system.

Greg argues that most nonprofits are still running outdated, transaction-first fundraising playbooks.

Measuring activity instead of building trust, surfacing intent, and earning the right to have a major-gift conversation.

The fix isn’t “more asks.” It’s a donor-driven approach built on signals, relevance, and disciplined follow-up, so engagement scales without losing the human element.

WHAT YOU’LL LEARN

1️⃣ Why transactional fundraising fails (and why donors disengage when they feel managed vs. known) 

2️⃣How to use donor intent signals to prioritize the right supporters at the right time 

3️⃣ Why major gifts behave like enterprise decisions, and what those changes in qualification and stewardship are

4️⃣ How to shift from organization-centric messaging to donor-driven engagement that earns meetings 

5️⃣ The leadership discipline required to make “heart” repeatable, measurable, and scalable

LINKS & RESOURCES

➡️Connect with Greg Warner on LinkedIn  

➡️ Check out Greg's (free) Fundraising Report Card and

➡️ Greg's (free) DAF Widget 

➡️ Visit the MarketSmart website

Transcript

Introduction to the Disruptor Podcast

John Kundtz 0:00

The donor-driven playbook: Engagement, qualification, and stewardship done right. Hi everyone, I'm your host, John Kundz, and welcome to another edition of the Disruptor Podcast. For those that are new to our show, the Disruptor Series is a blueprint for practical real-world experiences. We started the podcast in December of 2022. Our vision was to go beyond conventional wisdom by confronting the status quo and exposing the raw power of disruptive thinking. And today's guest embodies that spirit, Greg Werner, the CEO and founder of Market Smart, a philanthropy-based technology company helping not-for-profits transform how they engage major donors. In our previous show, we discussed Starting with the Heart with Bill Crouch, the CEO of Bright Dot. And today we'll explore how to turn the heart of fundraising into a repeatable operating system using donor signals, discipline qualification, and stewardship that scales. Welcome to the show, Greg. It's great to have you here. As I mentioned, this is a great segue from our previous show with uh um Phil, and I really look forward to it. But before we get started, why don't you just tell us a little bit about yourself, your background, your education, experiences? Feel free to start anywhere you want.

Greg Warner 1:29

Sure. Well, let's see. I grew up in New Jersey. Education, not a lot. No, I graduated college, but it's always funny when people ask about my education because I wanted to be a business major and I couldn't pass the prerequisites. So although I'm an entrepreneur, I've been a serial entrepreneur since I was a teenager. College pretty much told me I wasn't gonna be a business major. That was but I did graduate and uh ended up creating different businesses and eventually started giving more away. I didn't come from a philanthropic family. I had to learn how to give. I think most people don't really understand how to do it, in fact, but I was driven to do it. And then the more I gave, and when I got into the realm of giving five-figure gifts, you know, you put a little comma in there, you kind of maybe expect a little bit of different experience, but the experience actually got worse. And when I realized what was driving that, I I started, I actually offered my favorite charity free support, marketing technology, and that eventually turned into the company that is now today Market Smart. And that includes a little tool called the DAF widget, which helps generate more DAF gifts for nonprofits and the fundraising report card as well. But uh so I'm basically just trying to use technology, and by the way, I give away most of the stuff for free, but Market Smart's core platform does have a paid version. But I'm I'm trying to use technology to remove friction from the philanthropic process so that donors don't encounter the kinds of issues that I I ran up against that actually almost made me not want to give at all.

The Biggest Mistakes in Nonprofit Fundraising

John Kundtz 3:26

That's great background. It's funny, it's you're you're street smart. Sounds like we used to have a saying when I went to high school the the A's teach and the B's work for the C's. And so I I appreciate the people that are bootstrapped their careers and their businesses. And that's a great story. For those that don't know what DAF is, it stands for donor advised funds, and I'm a big fan of donor advised funds. I think they're a great way to take advantage of some of the tax laws, but also allow you to sort of take a step back and sort of take your time and really give from the heart and really get emotionally involved into an organization before you support them financially. You and I have both been working with not-for-profits for multiple decades. And I was curious on what do you think some of the biggest mistakes that you see not-for-profit leaders making when they're trying to take this, what I would call more of a traditional approach to major gift fundraising?

Greg Warner 4:28

I would say the single biggest mistake is that they have a mindset problem. They create self-limiting discussions in their brain, if you will. I don't understand wealthy people. I didn't grow up wealthy. That one had a silver spoon, you know, given they ought to give. We're awesome. So, you know, they should just we should go out there and twist some arms. You know, this is the self-limiting kind of self-talk leaders have. And even worse, there are some that just say, yeah, I don't really like fundraising, I don't care about fundraising, that's someone else's job. Which and these are just these are nails in the coffin for a mission. If if you want to just petition the government for money, maybe that's that's a better way. But a person with that that mindset, especially in a leadership position, well, probably should not be in a leadership position. The government is uh, as we all know, uh giving less priorities. It's the individual donors that will fund philanthropy. And uh if leadership uh has disdain or worse for the funding sources, it's just a recipe for disaster. So that is really because as the leader goes, so so does the rest of the organization. They're gonna bring in board members that that think like them, they're gonna bring in staff, and then they're gonna bring in a cycle, never-ending cycle of poor, unfortunate fundraisers who have kind hearts and want to do a good job, but are strapped with a leadership philosophy that is contrary to the word philanthropy. It's contrary to love. That's what it's all about. And if if the leader can't love the humanity of their funding sources, the individuals, so you're pretty much set up to fail.

Shifting Mindsets for Effective Fundraising

John Kundtz 6:43

That's great advice and great insight because I experienced something very similar many years ago. I was on a board, I've been on that board a long time, maybe over 10 years, multiple roles, led multiple committees, multiple studies. I was on the executive committee at the time, and they hired a new CEO. And we had a pretty decent endowment, but and did very little government contracting or grants. It was all private donations, mostly major donors. And for the first year of this new CEO's tenure, I would get to board meetings and I'd ask the guy, well, how many people did you talk to this last month? How many calls did you make? How many lunches did you have? Are you dedicating any time in the in during the week to call current and past donors? And I would get crickets. He had all those same excuses you just laid out. I don't like doing this, it's not my background. We're gonna go get grants from the government, the next, the next uh slate of officers. And I said, I'm sorry, I can't help. And I was traveling a lot for work, and I'm like, I can't, I can't be the bad guy in the meeting all the time. I can't really help you. And I unfortunately resigned from from that organization, and it was a great organization. And eventually they sort of figured it out, and eventually he they rolled him off a couple years later and hired another guy. We talk about these mistakes and this mindset. So, what would you recommend to organizations? What like shift, mind shift, mindset shift or habit would you wish every not-for-profit leader would adopt before they start overhauling their fundraising processes?

Greg Warner 8:20

That's a great question because I don't want to just pick on these leaders. I get it. They care deeply about the mission and they desperately want the mission to succeed. But like I said, they have these self-limiting way of thinking about money. And just imagine if like the head of General Motors said, you know, I really like to make amazing cars, but I just don't care about revenue or how I mean, I want revenue, but I really don't care about the customer psyche or any of that. I just, you know what, we make great cars, so people ought to buy from us, you know. And that just doesn't, that just doesn't work. Any exchange of money requires an exchange of value. In fact, probably equal or greater value needs to be received by the person who has the money in order to ensure that it gets conveyed. So, what I recommend though is that a leader who may be having some challenges with this part of the business should back up a bit and think about how they go about making decisions, big consequential decisions in their life, whether it's taking a big travel excursion, a big trip, or investing in a house or something like that, even a car, what they're gonna do is they're gonna, they're gonna think very carefully and and consider the decision and weigh it. And when they weigh it, they're going to meet somebody, or hopefully they'll meet somebody who will be their guide, their guide and counselor, facilitator, if you will. Like if you're if you're really investing in a big trip, you might get a travel agent, and that'll be your guide. If you're investing in a house, you're probably going to get a real estate agent, and that's your guide. So what those guides do first is they earn trust and they prove that they can deliver value. What leaders need to do is think about, frankly, that the there's sort of these frequently asked questions that a major supporter is going to wonder about the leader. The leader needs to have those uh prepared answers to satisfy the donor's potential fears and anxieties. So I'll just bang out a bunch of what kinds of questions these are. And I recommend that that any leader think about these really carefully in a way so that and almost practice them in in your mind to be able to convey to a supporter why they and the organization are worthy of their trust. So the the questions are basically the donor is gonna think, who who are you? You know, where did you come from? But then it quickly gets into what do you do? What can you do for someone like me? What is the value that you can provide to me? And how transparent and fair are you gonna be with me? And do you have some kind of process that can help me think through my decision? You know, and testimonials like do you have other people that have trusted you that you can tell me about their stories? And then what can I expect if I lean into this relationship further? At the next lunch, are you gonna pull out a proposal for a million-dollar ask? You know, I call this an ambush ask, and and so on and so forth. So you've got to prepare in your mind, frankly, that you are a facilitator, a guide, a mentor, a sherpa, a connector, an inspirational figure, you're a trust builder, you're not a beggar, you're not an arm twister, you're not a solicitor, you're a connector, you're trying to find the connection between an individual's motivations, their reason for caring about the cause and and and their timing, their interests, and what programs you have to offer that that align with their why and their values and their desire for a sense of belonging. If you can get that straight in your mind that you're a loving human that's trying to satisfy the needs of an individual who has wealth and help them share it for the good of everybody, and you get that straight, that you're not a solicitor or extractor of wealth, then you're truly, truly behaving in a in a philanthropic mindset. Does it make sense?

John Kundtz 13:26

It makes total sense to me. In fact, what you're describing is the traditional hero's journey, where you are not the hero as the CEO or the board president or whatever of the not-for-profit. You're not the hero. It's not because of you, it's not, they're not donating because of what you do. The hero is the donor, and you have to guide them through their journey through the all the canyons and all of the brick walls and all that stuff to the point where now they they they give again, as Bill mentioned, they give from the heart. Your job is to understand why they want to donate to your organization and what the value they receive they're gonna get, not the value of what you might receive, like a new building or new programming, or hiring staff or stuff they're gonna do. It's because of some other thing that either they some emotional connection into the organization. Makes sense.

Greg Warner 14:23

Yeah, and there's usually plenty of organizations that do what any leader's organization does. So what makes you different will be that you can provide value to that supporter. See, giving in a major way, especially when when when you're inviting someone to consider sharing their assets, which is completely illogical and unnatural, especially when you think about like a guy like me, I started working when I was a teenager, and now all that work, I'm just gonna give it away with barely any reporting, if if that, to know if my money was used fairly. It's completely almost illogical, and frankly, it's not done in so many countries and all around the world. In America, it's done. So you've got to see yourself as a connector and facilitator, and not as an extractor, and not looking down or or sideways at these wonderful humans. If you have issues with money, you have to unravel that first. And if you have issues with envy, you have to unravel that first. You can't ask someone or invite them to engage and share what they got and work so hard for so that you can win. That's very selfish and organization-centric, and the world revolves around a fair exchange. So, as much as a leader might be telling themselves that they're a great person because they lead a wonderful organization that does good work, they're not being kind if they don't lay down that sword. The word philanthropy means for the love of humanity, if you want to engage in philanthropic facilitation, you have got to love your brother, sister, you know, in this on this earth.

John Kundtz 16:34

I would add that major donors are gonna see right through those issues. They didn't get to where they are by accident. They're they're pretty savvy business people, investors, whatever. And they're gonna they're gonna recognize right away when you're desperate or you have a chip on your shoulder or whatever.

Greg Warner 16:51

You know, they're gonna worry being a snake, you know? Yeah, they can they can sense it when you're being disingenuous and you're flattering them. Flattery is often uh, you know, that's the first one. People think, I mean, that's it's such a cheap trick.

Building a Donor-Driven Operating Model

John Kundtz 17:08

That's the word disingenuous is definitely the word I was looking for. So all righty. So let's move on a little bit of like some of the stuff you you've been doing. So you've taken what I call the heart of the fundraising and you sort of translate it into this operating model that teams can execute. So I want to talk about what makes that approach essentially a strong bridge for not-for-profit leaders who sort of now understand the why is what we're talking about, but struggle with the what and the how.

Greg Warner 17:35

Yeah, this is a very good point because there are there's a conflict in our sector that's really hitting ahead. The sector's been operating on the same operating system for the past 50 to 75 years. You know, you get a data warehouse, it becomes mission critical, and then you're stuck with them. It's designed by people and for people who don't completely understand philanthropy, they understand transactions and they understand organizing receipt of transactions, but they miss the heart of the matter. And even if they could collect data on it, it's not it's not built for that. The whole sector is not built for major giving of philanthropic assets, whether while people are alive or after death. It's just not, it's built mostly warehousing transactions and monitoring activities of staff, meaning how many calls, how many visits, how many asks, how many proposals, how many gifts. None of that matters. What matters is what value are you delivering and is it helping people advance in the development of a meaningful gift that helps them realize the best version of themselves by aligning with a cause that shares their values, aligns with their life story, and gives them a feeling of a sense of belonging. So the architecture, the framework, the sector is is built on the wrong platform. What I'm trying to do is build the platform that really facilitates philanthropy. And like I said, I give most of the stuff away. The fundraising report card's been free for a decade. That's a metrics analyzer and visualizer for leaders and board and consultants to really understand their data so they can do effective planning in real time. And the DAF widget helps facilitate DAF giving. But then there's my core platform that actually is paid, which automates cultivation after engaging with supporters to learn their why. The thing about major gifts and legacy gifts is they don't happen quickly. So it requires surveying and capturing information that people are willing to share about their why. And then over time proving with automated emails mostly that your organization and leadership are worthy of their trust, and then gently offering them opportunities to move from thinking about their why to their what and how. And you can't skip steps. You have to start with why, that's the motivator, and then help connect them to the what that matters to them, the programs and such. And then finally, when they understand their why and the organization's what, and they start to see that they can gain value, meaning to live on in the lives or the minds of others after their lifetime, or to maybe value to them is to just be anonymous. You know, everybody has their different value, but as they start to realize that there is value in considering sharing, and they start to connect the dots on their own through almost Socratic self-examination, then they become ready for the how. And that's when it's a good time for, and that's what our system does. It's it's not well screening, it's all about donor intent and monitoring and collecting and taking the temperature and trying to understand when it is the right time to reach out to this person or to have the automation send them an email inviting them to set up an appointment on the leadership's calendar or board members' calendar to talk about. The why and the what, but then to start to think about the how. How are we going to do this? Are we going to do a retained life estate with this $3 million property that I want to live in until I die? But after that, I want to give it to the charity. You know, is it through beneficiary designation or a percentage of a business and so on? So there's a variety. But if you get to if you skip steps and go to the how first, which is generally, and frankly, a lot of planned giving departments, that's how they operate. They love their little tactics with regard to how to give. But if you don't do the why and and and then get to the what first, the donors are gonna reject any kinds of engagement and they won't advance and they won't consider developing a gift.

The Importance of Donor Intent and Long-Term Engagement

John Kundtz 22:50

I've been approached by a number of boards that I've been on where they say we be in plan giving. You just have to say you're interested or you'll do something. I've never heard from them in 10 years. I'm probably not going to remember them, or my estate's not going to remember that I even talked to them. And I think you're right, this is a long game. And it's it's like any kind of large, complex. We'll go back into the technology world I came out of, the large enterprise complex deals. Some some of the deals I worked on took two or three years, you know, but at the end, they were huge. And this is the same thing. I think the problem you have with what you just described, and what I think you're one of the values that that your system does, time goes fast. So you you can get heads down on something else, like the day-to-day stuff, the programming, and all of a sudden a year can go by and you haven't even you haven't even touched that that that potential prospect, if you will. And you've got to nurture those folks over, you know, could be years. And certainly you have to stay engaged and you have to take these little baby steps. And then we've had some of those by by accident where the person hadn't heard from a person in a while, and all of a sudden they come out of the blue and they say, Hey, I'd like to support XYZ. And you go, Whoa. And that, but that could have been a triple or quadruple gift if we hadn't spent a little more time understanding.

Greg Warner 24:18

This goes back to mindset, John, is that unfortunately, and and I really don't want to sound like I'm beating up on these folks. I I'd rather should say that I have empathy for them. Most people do not have experience with enterprise sales processes. Most people are not engaged in big decisions like buying a house all the time. The transactional mindset is more familiar to everybody. So there it's sort of like a black hole that the organization, the leadership, the board will gravitate to the black hole. They'll get the they'll they may get to the event horizon, but they often don't break free. And then they just fall right back into, well, how much money did we raise this month? Rather than considering who's in the pipeline, where are they in their consideration process? What can we do to add value so that they advance and move themselves forward? Because solicitation doesn't move people forward in an enterprise decision. It does in a transactional environment, but transactional environments only generate low-dollar cash gifts. If you want major, major gifts of assets and legacy gifts, you have to understand the enterprise sales process, and that requires patience and value delivery. It actually, our system never solicits anybody because we don't want a low-dollar gift. We want to bring a conversation together between the supporter and the leadership. That's that, like I said, my job is to remove friction from the philanthropic process. If you solicit, you're basically skipping to the how in a very major decision, and it just doesn't work. People are gonna retreat, and then then this is in fact why donor-advised funds have grown so much, because people would rather give to a rather faceless entity that allows them to be anonymous and get a tax break than give money to a charity that they're worried is gonna post their name and then let everybody in the world know and betray their trust, and then all of a sudden they've got everybody in town asking them for big gifts.

Conclusion and Final Thoughts

John Kundtz 26:45

It's funny, exactly what I did with my donor advice fund. It it allowed me to put a pretty significant in my world, you know, donation to the fund. But then it allows me to also answer the mail when somebody says, you know, can you give us you know $500 for an annual gift? And I'm like, sure. But it's they're missing the boat. I think donor advice funds are are very powerful, but they but they also I think uh allow us to fall into that black hole, so to speak. Now thinking about it, it's exactly what I did and why I use it. Anyway, let's sort of wrap this up. In conclusion, I'm reminded again of the book Start With Why by Simon Sinek. And he famously reminds us that people don't buy what you do, they buy why you do it. I always like to translate that into the not-for-profit world and say people don't donate because of what you do. They donate because of why you do it. And what you do simply proves that you what you believe. And Greg, what I appreciate about this conversation is how clearly you've made the bridge between the why from Bill's Crouch's work to the what. Really, this practical operating model that makes donor engagement repeatable, measurable, and scalable. So, my takeaway from our conversation today is heart without execution remains aspirational, and systems without heart won't scale.

Greg Warner 28:14

So, Greg, for listeners who want to learn more about your work, Market Smart, your donor-driven approach that we discussed today, where's the best place for them to start?com, the letter I, imarketsmart.com is our website. You can always connect with me on LinkedIn. I've got some 20,000 followers, and people contact me. I respond to everybody pretty much, unless they're asking me for money. So feel free to reach out. The fundraising report card is at fundraisingreportcard.com, and that's free. And then there's the daff widget at daffwidget.com. That's free too.

John Kundtz 28:53

We will put all of those links, of course, in the show notes so that you can find them easily. You also have a newsletter, I believe, that I I receive. I think it's weekly or I it comes periodically. So if there's some good information in there. Yep, thank you. I highly recommend that as well. All right, Greg. Well, I will give you the last word before we wrap up the show.

Greg Warner 29:16

Yeah. So hopefully this isn't controversial because I'm hitting it at the end. But you know, Simon Sinek talks about that people buy because of an organization's why. And I I like that. It's it's not bad. It's good. I love it. But when it comes to philanthropic giving and nonprofits, the why of the supporter, the supporter's why, the entwinement of their life story and history and how it relates to your cause, their values, their desire for a sense of belonging and community and meaning and purpose, their why is really what drives organizations forward. So I would just submit that gently and politely, that it's both the organization's why and the donor's why that matters in this space.

John Kundtz 30:20

I concur. In fact, I would say that's really the donor's why, but the the organization's why is important as well. I agree. I mean, you really have to empathize and understand the donor and the why they are doing what they're doing. Anyway, great advice. This has been fantastic. We'll wrap up the show. So again, thanks, Greg. Appreciate you spending time with me today. And I'm John Kunz, and thanks for joining us in this edition of the Disruptor Podcast. Have a great day!