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A
Hi everyone. I am thrilled to be here with you on this Friday, November 7th. I had to check the date. It's Scorpio season, it's full moon season. It's all the things year end giving season and that's what we're really here to talk about. I'm thrilled to be here with you on LinkedIn. If you're watching live, welcome. If you're listening later on Nonprofit Nation. Thank you so much for being a podcast listener. I treasure you and I love you. Today my special guest is Tommy Vosik and Tommy is the Chief Technology Officer at Bloomerang. We're going to talk about how AI can help year end fundraising overwhelm because what we know is that the final months of the year, well now we're getting into the final weeks of the year can feel like a sprint and it's often a marathon. On top of all of that, it's giving Tuesday, it's holiday campaigns, it's year end goals, it's outreach reporting, donor stewardship and just always that internal pressure to perform with limited resources. So today we're going to dive into the power and the possibility of AI. We're going to sort of strip away what is hype, what are the things you can ignore, what are the things you can prioritize, how to get started but also like if you are started, like what really to pay attention to and and how to really maximize what you're doing so that you can make the most of your year end campaign. So Tommy, we just met like a few minutes ago. Happy to have you here on LinkedIn Live and on the podcast. Welcome.
B
Thanks for having me, Julia. This is exciting. So it's a topic I'm very passionate to talk about as you would imagine. It's tough top of mind for a CTO when you're trying to drive technology initiatives internally at the company, but also from a product perspective. And so just like all of you, we are learning a lot and hopefully we have at least I have a few nuggets to share with with your audience today.
A
Yes, I have two quick promos. One is that the Nonprofit Social Media Summit is going to be held November 18th and 19th and it's totally free to attend virtually. I would be remiss not to promote it. So it's@nonprofitsocialmediasummit.com I will put that link also in the comments as well as a fabulous free resource from Bloomerang from our friends at bloomerang. It's 12 year end fundraising checklists. So if you are A checklist person and a planner. And you just love to see like a. To like, like what to do and how to do it and when to do it. And I know that I'm a huge fan of that. Go to jcsocialmarketing.com backslash bloomerang and you can get those checklists for free. So let's get this episode started. Let's start with your story, Tommy. What brought you into the world of nonprofit tech and what excites you most about your role as cto?
B
Yeah, thanks. Thanks. So I've been in technology my entire career, and I would say maybe I've taken. I don't know if it's atypical or typical. Seems like a lot of people find themselves in the non profit space in various different ways. You know, I started my career in fintech and sports technology and web hosting. And really what got me into non profit tech is I have a. I have a good friend that works here at Bloomerang and they told me about the opportunity to work at Bloomerang. I had never worked in the non profit space. You know, I obviously volunteered, donated, worked alongside non profits from that facet, but never worked in the tech space. And as I was talking to some of my friends about it, I had a couple friends that were executive directors at non profits here in Omaha and development directors. And every time I talked to one of them and I said, hey, there's this opportunity at Bloomerang. They said, oh, Bloomerang. We use Bloomerang. And then it connected the dots for me. And I'm like, I get to work at a software company that be able, that helps drive the mission of thousands of nonprofits and especially the ones that are near and dear to me and my family's heart. It was like, we get to make an impact on those through the software that we build. Like, if you can't get excited about that type of opportunity, I'm not sure you're going to get excited about too many opportunities. And so, you know, over the last three years, I've been very much immersing myself in the nonprofit space and learning how nonprofits operate, how, you know, the unique challenges that they have, especially with giving season coming up. I mean, we feel it here at Bloomerang and so have a lot of empathy for what nonprofits do with the limited amount of resources, in many cases that they do and the outsize impact that they drive. And so it's just an inspiring space to be in.
A
Well, we love Bloomerang. Bloomerang's longtime partner of mine, and I am not one to promote companies that I don't believe in and then I don't agree with and that I don't know that my clients love. My clients absolutely love Bloomerang. So let's talk about year end. It's so hard to believe we're talking about year end. I feel like it was just summer and then back to school and then Halloween. But it's famously hectic and stressful for nonprofit fundraisers. So from your perspective, what are you seeing as sort of the biggest stress points? And how do you see AI playing a role in sort of alleviating this stress?
B
Yeah, that's a great question. So looking at the data, we know that most organizations on average will raise about 30 to 40% of their donations in the month of December through giving season, if not more in some cases. And so you think about that amount of pressure going into that short amount of time period. It just creates a lot of natural stresses. And we're coming out of event season for a lot of nonprofits. And so people, staff members at nonprofits are coming out of, oh, I just got through this big event and I'm already behind on my strategy for the end of the year. And we see it all the time. And a lot of times then you get to the point of, okay, you have opportunity cost in front of you. Where do you spend your time? Do you spend it with the most important relationships that you have with your donors and your constituents and one on one time, or fostering those relationships? Or do I put to a broader cohesive campaign strategy so I can reach a broader base of my constituents? And a lot of times you're having to make kind of guesswork and say, where's the best use of my time? I think AI starts to change a lot of that because it's accelerating a lot of the things that maybe are what I'll call lower value time, which is the higher value time is spending time with the people that support your mission. Right. And that's where we want to make the most time for. The lower value time is running reports, segmenting your donors and constituents, filtering stuff in Excel spreadsheets, all the tedious and mundane things that we know are necessary to kind of rule out some of the guesswork and get to something really effective from a strategy. But that takes a lot of time. And so when you think about now, if you have the ability to connect AI to your data, whether that be your CRM data, your transaction data, your donor data, and be able to actually drive Real insights from that data. You start to really put rocket fuel into your ability to run really fast on the creation of the strategy and also the execution of the strategy, which hopefully frees up your time to then say, hey, I've got time on my hands where I can actually go call a supporter. I can go spend, go grab coffee with the supporter or donor and tell them what they mean to our mission to hopefully garner that, that extra push by the end of the year. And, and so I think AI is hopefully going to help for those that use it really well a bit to be able to do on both sides of broad strategy creation, execution and also the human relationship piece which we know is so important in the nonprofit space.
A
No, I completely agree and I think you made a really important point is that AI is obviously not replacing these more human touches that are so essential for, for a really sustainable long term fundraising strategy like meeting with donors or calling donors or talking to donors or even just, you know, going out in your community, going out and being on the front lines of the program, being in the trenches and like talking to clients and gathering stories. All of that. I always say that is our best, like last competitive advantage as nonprofits is those unique stories and that unique human centered element that we bring to the fundraising piece of it. But I, you know, I'm, I'm a huge fan of, of AI actually, what's so funny is I had a doctor's appointment this morning and I was talking to my doctor and I was telling her, I was explaining to her how I was just using it to meal plan and to get different ideas for Christmas gifts and things like that. I mean, just sort of like things that then I don't need to spend the time doing a ton of Google research and going down YouTube rabbit holes. Right. So how can fundraisers practically use AI during year end? Now there are sort of three elements that I know BlueBerang focuses on and that you talk about donor segmentation, copywriting and stewardship. Do you want to talk about those three?
B
Yeah. I think sometimes the most consuming, the most time consuming piece of your job is as a nonprofit leader is to actually logically break up your donors and your constituents into a meaningful way. Because we know every different constituent is on a different journey with your organization. You may have some early on that are volunteering and giving some hours and you may have some that are doing smaller, like one time gifts all the way to your major gift givers that are recurring on a regular basis and your outreach to each of them should be different it should be, it should be tailored to what each of those segments need to hear from you and where they are in the journey with your organization and kind of encourage them to take the next steps with the organization and get them inspired about what you're doing. But that takes a ton of time. And so if you think about the ability to take a list of your donors, their giving history, the different interactions they've had with your organization, the events that they have attended, you know, the calls you've had with them, and then you can start to pipe that into AI and say, can you logically break apart my, my donor segmentation and break them into certain groups? I mean, what took you maybe multiple days in the past can now take you a matter of 10 or 15 minutes if done. Well, now what I do want before I go to the next one, I want to encourage people don't hear me say go download a list of your CRM customers or your constituents and go plug it into ChatGPT. The, the donor information that you have, treat it as sacred. Be very.
A
There's a way you can anonymize it.
B
Yeah, you can and that's, you're 100% right. I would highly encourage you to anonymize it. If you're using a non commercial LLM, whether it be, hey, I just go sign up for ChatGPT or Claude or you know, Gemini, whatever it may be, don't put your donors data in something like that because there's no guarantee that they aren't going to use it to train or share or do something different with it.
A
That it's like we would never do that anyway. You know what I mean? It's just like you're saying, just use your own intuition. Like how would you use your, would you ever do that and export it and upload it into something where it could be used? We wouldn't do that.
B
Now where I get excited here is Bloomerang. We've been building, we built, building an AI feature called Penny and she's a chatbot that you can do a lot of this work. So we get excited about Penny because we now connect your, we can connect your donor data into a secured walled off AI LLM where we can start to do that work for you within our secure boundaries. And so kind of takes the best of both worlds where you can do some of that work, you know, where it took you multiple days ahead, you know, to segment your donors to. You can start to say, okay, I can do it in 10 or 15 minutes and create them into Groups and then create campaigns and actually have, have Penny help you write specific outreaches to each of those credit plan and then specific outreaches to each of the, each of those groups. And so that saves you a ton of time right there. Imagine saving a day or two during this critical season. That's, that's a huge win. And that kind of goes into a bit of appeal. Writing Penny will not only allow you to help with the content of what you need to put in an appeal, but it'll actually help you create a whole plan on how do you think about not just a one shot appeal, but how do you think about an entire, you know, multiple outreaches throughout the entire month of November and the month of December and how often to reach out to somebody what to say in each, each, each outreach, because you need to at different levels. You need to be a little softer and then be more direct on asking in certain areas. And so maybe your mission up front, where you've made impact, where your vision is and where you're going for the future, and then go and ask for, you know, a donation or specific amount. What's great too is with Penny being connected to your data, you can be better about specific personalization pieces as well. And so now if you think about it, I don't have to send a generic appeal. I can actually write specific appeals to each constituent. And so Penny can help and say, hey, for Julia. I know Julia is into a certain hobby or a certain thing or I knew she went on a trip this year based on a previous conversation we had that we had a note in our CRM and I can say, hey, Julia, I hope you had a great trip this summer and start to engage them on a personal level, which I think is, we know the human relationship and the human connection there is so valuable and so important and it separates you from just the generic appeals that get sent to everybody. And so you're going to have a likely higher impact or higher response rate on those, those type of appeals. And so Penny being able to help us with things like that is great. And then just, you know, the, the stewardship piece, there's, there's a lot of just touch points along the way. We, you know, there's, there's times when you just want to have a personal outreach to a donor and say thank you for a certain gift. And so we've actually also built inside of Boomerang video acknowledgments. Where on our mobile app, a video acknowledgments.
A
I love it.
B
Yeah. And this so this is, you know, it's connected tangentially to AI, but it was a feature that we built regardless of AI, and it's, hey, you're a staff member at a nonprofit. Julia just gave a large gift, or not even a large gift, just gave a gift. Now I can get prompted and say, I'm going to record a thank you video for Julia and have it get sent to her directly. And so something nonprofit staff members can use on the go. And you don't have to put a lot of thought into it. It can, can feel very organic. And, you know, I can jump on my, my mobile device and record you a quick video and then send it off. And so the stewardship and the fostering of that relationship is something that to also focus on regardless of AI, you just have to do that. But hopefully find, find a tool that can help you help me make that easy.
A
I, I love that piece. I'm just writing down personalized videos because I, I did a webinar on how to send a personalized video, and it was so successful. But I think where nonprofits struggle is like scaling, and that's really where I can help you scale. I don't think you need to say you can. And I would love it if you could say, hi, Julia, I really appreciate your 500 gift. But even if it's just every time someone gives to you on Giving Tuesday, sending a quick video that says, wow, you really made a difference. This is amazing. Like, you're a wonderful person. You've joined a movement that's bigger than you. Here's where your gift is going. Here's what we're going to do. Here's our vision for the future. Just any way that you can use AI and these tech tools to scale stewardship. Because I really know, like, for me in my work that I do with my clients, it's a lot about donor acquisition. It's a lot about marketing and outreach. How do we get more donors? How do we get eyeballs of more donors? How do we get the attention of more donors? And then what happens after your end? Like, that stewardship piece is so important. Another an example that I would give of an organization that I give to every year is the Wikimedia foundation that funds Wikipedia. Just sign up. Just give them $5. You will not regret going on their email list, the personalized subject lines, the email that makes me feel like it's written to me, even though they probably have millions of donors acknowledging my last gift and asking me if I could just give like 25 more this year, it was asking me to become a monthly donor. And I'm thinking, why didn't I think of that before? But just those touches of like Julia's given to us for five years, we should probably ask her to be a monthly donor. And it just makes so much sense. Like, it doesn't seem like it's coming out of nowhere because they're looking at the data, they're looking at my history, they're looking at how long I've given and how much I've given. So it doesn't feel like it's coming out of nowhere. And that's how I love. I love to teach nonprofits these tools to scale that kind of personalization. And we don't often think of personal personalization being something that we can scale, but I think if we do it intentionally, we can do it really well.
B
And it doesn't. It doesn't take much to stand out.
A
Yes, it doesn't take much to stand out. Let's just. Let's put that on a billboard. It does not take.
B
You would see my. If you. If you see my email right now, you'd be like, oh, my goodness, that's a mess. And it's like, if I could. If I could look at one email and there's just a little bit of a personal, personalized touch to it, my chances of open, opening it, doing something with it, responding to it, engaging with it, is so much higher than just a generic email that, you know, we all look at everybody's inbox. It's just full of stuff right now. And so just do a little. Do the extra 10 and stand out. And that's exactly where AI is going to help you, is making that party good. But that 10 is hard. It's hard to know how to personalize a message to somebody, especially doing at scale. Use AI. It's going to help you do that very fast and at scale. So there's a big unlock there.
A
Okay. All right. Oh, my gosh. Okay, so let's keep going. In your view, what skills should non profits speak start building now to work alongside AI and not be sidelined by it?
B
Yeah, I think the practice is one of the most important things to start with. I. I think about my early journey with AI. You know, first when ChatGPT came out, it was a novel new thing. The quality of my prompts that I gave into ChatGPT were looking back, were kind of. Kind of funny looking back. But it was necessary for me to go on a journey of learning how to ask better questions. Learning how to prompt, taking training on it. There's tons of Google, Gemini has a bunch of free training out there. There's a ton of YouTube videos on how do you learn how to become a better prompter? We're publishing a prompt library to help nonprofits understand how can they just take a, take a prompt from our prompt library and plug it in and get real value out of it. But you have to, you have to spend time with it. You have to put the reps in. It's just like practicing anything else. You're going to get better with it over time. You're going to understand how the tools work and your better input is going to produce a better output. And the thing that I would also encourage you too, as you're learning how to prompt better. Don't take the first response from some type of LLM as that's gold. I'm going to go run with it. Treat it as a colleague that you're interacting with. And so if I'm working with somebody on my team, I'm going to give them context of a problem. They're going to give me some feedback on, hey, here's how I can go solve that problem. And then I'm probably going to be like, oh, you made me think of something else. I'm going to give you additional context and continue to refine over and over again. It's not a, I think a lot of people think of Chat, GPT or Claude as a one shot. I'm going to get an answer and I'm going to go run with it. Put the, put the back and forth into it. You're going to get a much, much better output as you, as you have a conversation with AI and so think of, think of it as a thought partner as you, as you go with. I also think don't get overwhelmed with I've got to know everything about AI to start. There's a huge bit of a barrier. We've done some surveys with our customers and we did a survey a year ago and the sentiment around AI was very negative. And what I would say over the last 12 months it's dramatically changed. But there's still a bit of a sentiment of I'm nervous about it, I don't know how to use it, I don't know how to engage with it. I would just encourage folks not to get overwhelmed with that. But just like trust with anything. You have to start small and you have to build over time and so don't start with the biggest problem that you have as an Organization start with something very, very simple. Maybe it's just a, I want to send a handwritten note to one of my constituents. Can you help me craft a really thoughtful handwritten note that I can transcribe and write out to them? And that's, you know, there's no harm, no foul in that. If it produces bad quality, you're going to see it and you're not going to write the note or you're going to write one yourself. But start small with little things like that, and then over time, build on the trust that you have with your ability to use the tools and how the tools work and start to work on more complex things. And then I would say privacy, accuracy and transparency around AI tooling is you have to start to do your homework. Not every tool is made the same. Not every tool thinks about privacy the same way. You also have to understand that AI does hallucinate. We've all heard of the hallucination things. And so the best you can do is you can sometimes respond to an AI answer and say, how did you come up with this answer? And have it actually respond to you and describe, hey, I took it from this sources, or here's my logic on coming up with this answer. That's going to help you feel more convicted about the content that's coming back to you. And then also what I would say with AI too is we serve a lot of environmental organizations. And so what I would say is, as you're evaluating tools, this is something we think a lot about at Bloomerang is we have a stewardship to use the right models for the right tasks. And so you go into ChatGPT, you go into Claude, you go into Gemini. There's different models that you should be using for different tasks. And why that is important is each of those uses a different amount of compute, uses a different amount of energy. And so, and we think about this when we build our products, when we build Penny, we want to use a different model for different complexity of tasks. We shouldn't be, you know, using a jet engine. For every single question that comes across, Penny, there's some that we can actually use a much more efficient, a much cleaner model for some, some simpler type type of tasks. And so understanding that not every model is made the same, do some research, especially if environmental concerns are important to you, do the research on what's better to use there.
A
I agree. And wow, you actually preempted my other question, which was about the ethical integrity of using AI. When people ask me this, I say, really is beyond my scope of knowledge. But we all have to be very conscious as to the tools that we're using. Are you on X? Then you need to be thinking about the ethical implications of being on that. Are you on Meta? Are you on Tik Tok? I. So it's not a. It's not saying that, oh, you know, one is better than the other, one is less evil than the other. But in my work, when I teach digital marketing and I teach social media, and then people say, well, what about the environmental. Environmental implications of using AI tools? I say, that is certainly something we need to be thinking about and asking about. I am not the expert in this, but if this is something that troubles you, then by all means. I mean, like, there's nothing in any world that says we have to be leveraging these tools. And I really appreciate what you said about, you know, right size and responsible, like, match the model to what you're trying to do. So, you know, I, I think that these are really good questions to ask, and I think we, as thought leaders in this field, I think it's a good idea to be asking these questions because I know I certainly get asked these questions quite frequently. But, you know, when I teach about social media, I sometimes have to say, oh, am I really telling you to spend money with meta ads? Like, I don't know, I'm not, I'm. There's no one size fits all. And it's all just, is this going to. Is this going to further your mission and really help you make, like, make a huge impact at the end of the day? And I think a great example of that is the way that organizations recently have used their platforms and even AI tools to advocate for SNAP benefits and to advocate for food security. So I think, you know, I just. There's so many interesting questions to be asked here, and it's just such a new frontier. But I do understand Bloomerang has its own AI feature and this is Penny.
B
This Penny.
A
I know you shared a little bit about how you built the tool, but really, can you dive a little bit more into, like, what problems it's designed to solve for fundraisers and like, maybe why it's different from other tools.
B
Yeah, great question. So I'm, I'm personally very proud of Penny. Penny, I think, is going to change the way that customers interact with Bloomerang in general. Our products, our expertise. We actually have Penny live in front of customers right now and do an alpha stage. And so it's a big milestone for us as a company. Penny was A bit of a where Penny came out of is we looked at, we have a coaching and consulting offering at Bloomerang where we will one on one coach and consult with a non profit organization. And what we do is we do intense look at their data, lapsed donors, donor retention year over year, giving their rate of turning one time donors into recurring donors. And we have set playbooks that we have built over the years based on our experience, based on nonprofit experts. And we will implement those playbooks with the nonprofits that we coach. And we know it has a massive impact on moving those metrics in the right way. And so we did this on a one on one basis and we're like, well, why can't we do this for more of our customers? And that's kind of where Penny queued into. And we said, well, with the acceleration of AI technology coming out, I talked about earlier where it's great to connect with AI with your data, but where I think Penny is, is going to be set apart from anything else that's being done in the nonprofit industry is AI plus your data plus expertise. And it's deep rooted expertise. It's not expertise that we came up with just by asking ChatGPT. Bloomerang is well known for all the expertise that we put out from a marketing perspective on webinars on our marketing site. And it's, and it's rich, there's a lot of important content in there. But it's also those one on one coaching calls that we have with our nonprofits where we've built these playbooks. Well, we built Penny on top of these playbooks. And so when we're giving you advice, it's not advice that comes generically from an LLM somewhere that could be hallucinating or it could be misguiding somebody because it doesn't have all the context of your organization. And so we built playbooks specifically on handling lapsed donors and how to re engage with lapsed donors. We've built playbooks on how to turn one time donors into recurring donors. We've built playbooks on how to run events and auctions in the most effective way. This is the knowledge that Penny is built on. And it's not surface level knowledge, it's deep. And you can engage with it, you can ask for clarifying details, you can ask for additional kind of levels of what do I do after this step. And that's where Penny helps quite a bit, is any nonprofit staff member can come to Penny with their problems and it can analyze their data, it can give you recommendations on a strategy for the rest of the year. I think it's really relevant right now for into your giving, which is, hey, how do I engage with my constituent base in the most effective way? I have a very limited amount of time. I have very limited amount of the ability to send out outreach campaigns. I want to get their attention the best of my ability. And Penny can help walk you through a strategy to go do that. And so that's one good example of it. Penny can. I mean, there's a number of different things that Penny can go do, just even if you want to help engage. This is a fun example that we. We were playing around with Penny internally the other day. A lot of executive directors and how to interact with your board is a really challenging relationship.
A
Yes, absolutely.
B
So now, you know, asking Penny to say, hey, can you give my board an update on the things that we've been doing from an. From a outreach standpoint, a campaign standpoint, how we're doing from a overall fundraising standpoint, And Penny can help craft that message again with your data and the expertise and actually craft an outreach to your board, help you prepare for a board meeting and give you all the things that you should be talking about, but also the really fun one that we enjoyed, which is how do you, in a good way, in a kind way, get your board to actually make a donation to the nonprofit that they're serving. That. And so we. It was funny to see Penny actually, you know, because you're a board member, you're assuming that you're supporting the nonprofit. And so it's like, hey, from a leadership perspective, I know that's a really hard thing for an executive director to go to a board member and be like, hey, we want your support as well. And so we. We had to craft a message to the board member and say, hey, we also, we have a campaign coming up. We'd like you to personally think about giving. And I think it sets a good leadership tone. And so that's a really. It's a really challenging conversation, I think, for a lot of executive directors to have. And so helping. Helping overcome some of that fear is something that we can. We can do with Penny.
A
I think a great way to use it would be to say to Penny, what are some questions that you think the board is going to ask me at the next meeting? Like, prepare. Almost like an executive assistant, like, based on, you know, upload your last 10 agendas and say, okay, here were some sticking points at the past few meetings. What should I prepare for at this Next meeting. Yeah. And to just give you sort of an insight into some questions that they might ask. Like, they're. Maybe they won't, but. And then also, I think what we get wrong with boards is we assume that they know everything that we know.
B
Right.
A
And so asking Penny, like, what are some. What are, like, top. The top five things that we've done this year that maybe the board doesn't know about? Or, like, what are some, like, great ways that we can share stories with the board, ways that they might not know? And, you know, the way I always talk about AI is the executive assistant that I don't have, you know, asking questions, doing research, fact checking, editing, looking at things from a different perspective, asking me questions. I love. I know. I love using ChatGPT to ask me questions like, what am I not thinking about here? Like, what am. What am I getting wrong? What are some of the things that I should be looking at? What are some angles I'm missing? And I think that's a. That's a really great way to use it. I do have to ask you, is Penny named from Peewee Herman?
B
No, I. I'll give you the.
A
Or from Danger Mouse. Is that Penny?
B
Nope. I'll give you the story. So it actually. It evolved over time. So being a nerd, when we kicked the project off, I'm a big Batman fan. And so Alfred Pennyworth is butler. And so the whole analogy from an internal project perspective was we're kind of like, you know, we're kind of the Alfred at Bloomerang, and the he Hero Batman is. Are the nonprofits that we serve. And so we're in the background doing all the hard work of making all your data come together, getting you what you need, and helping you be an effective hero. And so I thought that was a cool analogy. When we started Project Pennyworth, well, one of our nonprofit experts, as we were building out, Pennyworth, kept referring to Pennyworth as Penny. And we're like, we love the Persona. There's a lot of, I think, importance built into the idea of Penny. There's a lot of cool sayings like 2 cents for your thought, or those type of things. But there's a ton of female leadership in the nonprofit space. And we felt it was incredibly important to have a female Persona with the AI Chatbot that we use. And so Penny just really stuck. And it was interesting. We went through with some of our brand partners, and we went through a bunch of different ideas, and they came back to us and said, we think you guys should go with Penny. And so it was a bit conf. Confirmatory of like, Penny's. Penny's a great name. There's a lot of meaning, there's a.
A
Lot of substance, a lot of pop culture associations.
B
Right. And so we're, we're really proud of the name of Penny. But it's, it's kind of fun to see the, see Penny take a life of her own at this point.
A
I love it. Well, as we wrap up our time together, what is one piece of advice that you would offer to a small nonprofit team that is really feeling overwhelmed heading home into your end?
B
I would encourage you, just as I was kind of talking earlier, take shots on goal with AI you're going to have to learn how it works for your organization. Everybody's on a different part of their journey. The best thing that you can do is to engage with it, engage with small experiments. Don't feel like you have to hit a home run out of the gate. Do the little things, start to build up some momentum, do some more complex things. I would also encourage you to get educated as best as you can. Understand the security around it. This is the nerd coming out of me again. But the transparency, the ethics, the environmental concerns, all those things wrapped together. You should get some base level of education of the tools that you're using and how the company that's built those tools is thinking about those different type of things. Because not every company is made the same as we all know. And so if you're, if you're applying a tool to the most important mission that you're working on, you want to make sure that it aligns with, with you, with your ethical concerns, your, your security concerns, your just how you think about trust and transparency. So do, do, do your homework on, on what, what, what tools out there. I think that's where we at Boomerang feel really strong is we've, I believe we've done the hard work as a company to build the trust with the non profits that we serve and everybody in the industry. And so we're not a new startup. We're not, you know, coming at this just to land grab what we're doing about this. What we're doing with Pennyworth or Penny is to say, how can we make more time for human relationships? How can we give you more time back in your day? And how can we give you a better tool set to really enhance the mission that you're focused on? And so go do the homework, go do the experiments and start playing with it.
A
Oh, I love that. I'm not sure if anyone has any questions. I don't see any in the chat. And if you do have questions, definitely you can post them later. We will follow up with you. But Tommy, where can people connect with you? Connect with Bloomerang. Learn more about the tools and the services that you offer to non profits.
B
Yeah, just head out to bloomerang.com you can see our entire giving platform out there. Fundraising tools, CRM tools, volunteer tools. Also we do have a page that talks about Penny. So if you just search for go to bloomerang.com blog meet penny. You can learn about Penny and learn how you can start to engage. Engage with her is another way to to see what we're doing here at Bloomerang.
A
Yep. So that is bloomerang.com blog meet-penny and then if you want the fundraising checklist, go to my website, jcsocialmarketing.com bloomerang and also if you want to join the nonprofit social media summit, all virtual, all free in November. Lots going on. So many resources to help. Bootstrapping under resourced, struggling, stressed out fundraisers at year end. I really appreciate your time. Tommy. Thank you so much for coming on and sharing all this great information with us.
B
Yeah, thank you, Julia. It was a pleasure. I hope it was insightful and helpful to those out there. So thank you for having me.
A
Yes, thank you. Everyone else, have a fantastic day. If you're listening to the podcast, thanks for listening and until we meet again, have a great weekend, everyone.
Guest: Tommy Vacek, CTO at Bloomerang
Date: November 10, 2025
This episode explores how artificial intelligence (AI) can be harnessed to reduce the overwhelming stress of year-end fundraising in nonprofits. Host Julia Campbell and guest Tommy Vacek delve into the practical ways nonprofit professionals can incorporate AI for donor segmentation, personalized communication, and stewardship, with a special focus on Bloomerang's AI tool "Penny." The episode balances practical advice, ethical considerations, and a look toward the evolving landscape of nonprofit technology.
"Do you spend it with the most important relationships that you have with your donors and your constituents and one on one time... Or do I put to a broader cohesive campaign strategy so I can reach a broader base? ... AI starts to change a lot of that because it's accelerating a lot of the things that maybe are what I’ll call lower value time."
[09:37] Tommy discusses three key AI leverage points:
"If you’re using a non commercial LLM...don’t put your donors data in something like that because there's no guarantee that they aren’t going to use it to train or share or do something different with it."
"Imagine saving a day or two during this critical season. That’s a huge win."
"Any way that you can use AI and these tech tools to scale stewardship...it’s a lot about donor acquisition...and then what happens after year end? That stewardship piece is so important."
"If I could look at one email and there's just a little bit of a personal touch to it...my chances of opening it, doing something with it, responding to it, engaging with it, is so much higher."
"Your better input is going to produce a better output...Treat it as a colleague that you’re interacting with."
[24:06]
"Are you on Meta? Are you on TikTok?...There’s no one size fits all. And it’s all just, is this going to further your mission and really help you make a huge impact at the end of the day?"
"Where I think Penny is going to be set apart from anything else...is AI plus your data plus expertise...not advice that comes generically from an LLM somewhere that could be hallucinating."
"We felt it was incredibly important to have a female persona with the AI chatbot...Penny just really stuck."
[35:05]
“Take shots on goal with AI. You’re going to have to learn how it works for your organization. Everybody’s on a different part of their journey...Do the homework, do the experiments, and start playing with it.”
"Even if it’s just every time someone gives to you on Giving Tuesday, sending a quick video that says, 'Wow, you really made a difference.'"
"It doesn’t take much to stand out."
"The way I always talk about AI is the executive assistant that I don’t have...asking questions, doing research, fact checking, editing, looking at things from a different perspective."
| Segment | Timestamp | |----------------------------------------------------------|---------------| | Introduction, AI & year-end stress context | 00:01–05:33 | | Tommy’s journey to nonprofit tech | 03:09–04:50 | | The AI opportunity: stress relief for fundraisers | 05:33–08:00 | | Key uses: segmentation, copywriting, stewardship | 09:37–15:40 | | Personalization & impact of small touches | 15:40–19:06 | | Skills for working with AI | 19:06–24:06 | | Ethical/environmental considerations | 24:06–26:28 | | Penny AI: what, why, and how it works | 26:28–31:34 | | Fun with Penny & board engagement | 30:21–33:10 | | Why "Penny" and the importance of branding | 33:05–34:51 | | Closing advice: using AI in small orgs | 35:05–36:51 | | Where to learn more, connect, and access resources | 37:12–38:14 |
Julia and Tommy’s conversation is both hopeful and grounded—AI is not the enemy, nor a panacea; it’s a powerful tool that, when approached thoughtfully, can give precious time back to nonprofits to focus on the human side of giving. Penny stands out as a practical example of AI tuned specifically to nonprofit realities—secure, expert-informed, and accessible.
Action Steps for Listeners:
Learn more:
A final word from Tommy (35:49):
“How can we make more time for human relationships? How can we give you more time back in your day? And how can we give you a better toolset to really enhance the mission that you’re focused on?”