Webinar

Meet Penny: Your fundraising sounding board

Fundraising is entering its next chapter. In this webinar we explore how Penny, Bloomerang’s intelligent fundraising partner inside the Giving Platform can support your mission’s success. We’ll discuss what happens when years of nonprofit expertise and trusted donor data come together — revealing clearer focus, smarter decisions, and momentum you can feel.

Learning objectives:

  • Prepare for donor meetings with confidence
  • Instantly identify priority donors and opportunities
  • Get guided next steps backed by proven expertise
  • Automate actions directly inside Bloomerang
  • Use AI with clarity and control

Transcript:

Katie Gaston: Welcome, everyone. Thank you for joining us today. We’re going to get started in just a minute or so, but we are really excited to spend the next forty-five minutes introducing something we believe will change how fundraisers like yourself work.

Before we get started, we’ll give it just a minute while more people join. Put in the chat where you’re joining from, and in one word, how does fundraising feel for you right now? I’m so curious to see where the furthest person is joining from. Go ahead and put it in the chat. Lewisburg, Philly, Pennsylvania, Florida, Texas. I can’t even keep up with them. I saw the Philippines. That’s impressive.

How does fundraising feel? Overwhelming. Exhausting. Hectic. Frustrating. Heavy. Slow. Oh my gosh. I did see “fabulous,” and I like whoever put that one in. Thank you. We’re going to see if we can solve some of these words today. Keep putting them in the chat. This is going to be an interactive session, so we’ll have some polls and some chat throughout.

Before we get started, I know many of you may be wondering a few things. Yes, we will send a recording of this webinar. If you have a colleague who wasn’t able to join, watch your email in the day or so after this and you’ll get the recording. Feel free to ask questions. We’ve got some team members in the back supporting and making sure your questions are answered as quickly as possible. And like you’re already doing, engage in the chat. We’re all in this together. You are a network of fundraisers, so being here to support each other, share your story, and interact through today’s webinar is perfect.

With that in mind, I think we’re ready to get started. I’m excited to introduce my co-presenter today, Tommy Vacek. Tommy, do you want to tell us a little about yourself and the work you’ve been doing with Penny?

Tommy Vacek: Yeah, thank you, Katie. I’m excited to be your co-host today. I lead technology here at Bloomerang, and Penny has been one of the most energizing projects I’ve worked on in my entire career. A lot of things drew me to this project and what we’re solving, but it’s really the incredible work that all of you do at nonprofits. It’s incredibly important work. Often, teams are stretched incredibly thin. You have tools that aren’t optimized or built for you. You don’t have enough time in your day to be as intentional as you want with the most important relationships you maintain.

That gap between what fundraisers know they should be doing and what they have the capacity to do is what Penny helps close. Over the past few weeks and months, we’ve gotten into the weeds with customers to understand how their teams actually work, where the friction is. We’ve identified a lot of opportunities and built them into Penny, and we’re going to talk about a lot of those today.

Katie Gaston: I love that, Tommy, and I’ll echo it. I’ve had so many conversations with many of you over the last few months about Penny and about your experience as a fundraiser. One thing we hear a lot is that sometimes you think you know the best path, but you’re a team of one. You don’t have someone to bounce ideas off of. I think I saw one of the words in the chat was “lonely.” A hundred percent. Sometimes all you want to know is that you have the tools and resources you need and that you’re making the right call. That’s one of the things Penny can do for you.

So for the next forty-five minutes, we’re introducing Penny, the strategic fundraising sounding board built directly into the Bloomerang Giving platform. Before I tell you exactly why we built Penny, I’m going to launch our first poll. When you’re making a fundraising decision today, what creates the most uncertainty? Are you focusing on the right donors? Do you feel you might be missing important information? Are you making the right ask? Or, and I think a lot of you can relate, are you just running from task to task without enough time to think it through? Go ahead and complete that in the chat and let’s see the results.

It’s fairly evenly split. Thirty-four percent say you just don’t have enough time to think it all the way through, and then you’ve got a few other ones as well: Am I focusing on the right donors? Am I making the right ask? Or is there information I’m missing? We’re going to talk through all of those today.

Let’s talk a little about what Penny is before we show you what she can do. Penny is your intelligent fundraising partner, built directly into the Giving platform. As a fundraiser, you can ask a question in everyday language and, through your own data, immediately understand which donor needs the most attention and who Penny believes, based on everything she’s analyzed, deserves personalized guidance.

All of Penny is shaped by proven fundraising success. We’ve taken thousands of consulting wins from over a decade with Bloomerang and built a lot of that strategic guidance directly into Penny. Combined, Penny not only helps you understand who to focus on and gives you strategic guidance and validation, but also helps you take action directly in your Bloomerang Giving platform. Penny gives you the clarity, the confidence, and the capacity to do what matters most, which is building meaningful relationships with donors.

We’re going to talk a lot about this: Penny is built on secure AI design practices. She looks at your data securely within the context of your database, not on a third-party tool, grounded in your data and, like I said, built on thousands of successful historical nonprofit consulting wins.

Tommy, you’ve invested quite a bit of time in Penny over the last several months. What does Penny understand about fundraising that generic AI tools can’t today?

Tommy Vacek: That’s a great question, Katie. Generic AI tools are built for everyone and for a lot of generic tasks. They’re not optimized for different workflows. They’re not built off your context as an organization, your data, and expert playbooks around fundraising. You mentioned we’ve had thousands and thousands of coaching and consulting sessions. We know best practices on what works for nonprofits, and we’ve built Penny on top of a lot of those experiences.

So she understands the donor life cycle. She knows what a lapsed donor is versus a disengaged donor, what signals suggest somebody’s ready for a major gift conversation, and what healthy mid-level retention looks like. That isn’t context you’re going to get from a general-purpose tool or a public LLM.

The other big differentiator is the playbooks we built. Penny’s recommendations aren’t generated just from concepts on the open internet. They’re grounded in expert fundraising strategy, the kind of thinking the best development professionals use to build and sustain major donor relationships. When Penny tells you to prioritize a specific donor and gives you a reason, it’s not a probabilistic guess. It’s very deterministic. It’s a recommendation backed by how great fundraisers actually think.

Generic AI can’t help you do that. It can’t help you draft an email that’s going to hit one of your most important donors in a really effective way. Penny tells you who to send it to, why to send it to them, and what to send. Providing context for improving that relationship is something Penny can help every nonprofit professional with.

Katie Gaston: A lot of what you focused on there is that Penny is secure in a nonprofit’s own data and isn’t referencing external data. When I’ve talked with fundraisers over the last few months, as we’ve brought Penny to our entire customer base, they ask, “But is it secure?” Could you speak to that and share how she’s constructed on the back end?

Tommy Vacek: Yes. We didn’t build Penny and then say, “Privacy and trust are important features we need to add.” They’re foundational to the way we built Penny. It starts with the data we’re stewarding. We’re stewarding donors’ information, the most important information to you as an organization. These are people who give volunteer hours, give monetarily, give their energy to your organization. It’s really important that we help you protect that data.

These are real people who’ve made a decision to support your cause. That relationship is sacred, and any tool that touches data like that needs to be built primarily on trust. Penny is inside the Bloomerang Giving platform, a platform your team already trusts and relies on. We’ve spent years earning the right to that trust. So when you use Penny, you’re not stepping outside our trust environment. You’re working within it.

Penny does use large language models to power some of the intelligence, but we’ve done it the right way. We have enterprise agreements with all of our AI partners. We handle those partnerships the same way Bloomerang handles any other trusted third party. We have contractual data protections, and we have promises and assurances that none of your data is used to train any public models. We take those governance standards very seriously, and we won’t work with vendors that don’t. Privacy and trust aren’t check boxes for us. They’re the core pillar of how Penny was designed from day one, because if your donors can’t trust you, you can’t trust the tools you’re using, and none of it works if that trust isn’t established the entire way.

Katie Gaston: Thank you so much, Tommy. With that in mind, who wants to see what Penny can do? I think I’ve seen a lot of that in the chat. Normally we have a Q&A portion at the end, but there have been some great questions in the chat, and Tommy, if you’re okay with it, I’d like to walk through two right now. William asked earlier whether Penny is an add-on subscription or part of the current subscription. Do you want to speak to that?

Tommy Vacek: Great question, William. Penny is turned on for every CRM customer we have on Bloomerang, and we’re very excited to announce that. We’re still in beta, which means you’re seeing a lot of rapid iteration and lots of improvements. While we stay in beta, Penny is available at no charge to everybody. As we learn how Penny evolves, we may have to figure out some of those things. But while we’re proving the value and getting Penny in front of you, she’s available to every single Bloomerang customer through the beta process.

Katie Gaston: Amazing, thank you. And Jill, I saw your question, and a lot of folks were interested in it. We’re going to talk about other use cases, but the short version is that Penny can help you clean up your data automatically in the CRM, as well as make recommendations to clean it up. That’s a great transition, so let’s see Penny in action.

I’d love to hear from some of you. We’ve all been in a scenario where we’re new to an organization, and you’ve likely, at some point in your career, inherited a messy database. It sounds like Joe, maybe you’re in that situation today, or have been in the past. When you step into a new fundraising role, what feels most challenging? Let’s see the feedback, either in the poll or in the chat.

I can understand and appreciate that. This is pretty evenly split as well. Juggling responsibilities, a hundred percent. Donor data is a challenge. Feeling confident in the history. This is a real challenge. You want to jump in, get started, and prove you can make a difference quickly. Let’s see a clip from Summer on our marketing team talking about how Penny can help you get started when you step into a new fundraising role.

Summer Interior: Hi, I’m Summer, a campaign manager at Bloomerang. I know that starting at a new nonprofit can feel overwhelming. There’s donor history to learn, reports to untangle, and fundraising goals you’re already responsible for. Too often, the context you need to succeed walked out the door with the last fundraiser.

Today I’m going to walk you through how Penny supports nonprofit fundraisers when they’re new to an organization and need clarity fast. This is what I’d ask Penny: “I’m new to this organization. Based on our data, what are our biggest fundraising opportunities?”

Because Penny is the AI fundraising partner built into the Bloomerang Giving platform, she can see your full donor picture, giving, engagement, and relationships, all in one place. Penny walks through exactly what she’s analyzing: recent donation activity, donor retention patterns, transactions, and your overall constituent base. That transparency, grounded in your own data, helps you trust the recommendations that follow. Within seconds, Penny gives me a clear snapshot of our active supporters, recent giving activity, and overall momentum.

Katie Gaston: Amazing. I love that clip because all of you have experienced that before, and this is a real scenario where Penny can jump in and help. Tommy, what do you feel changes when you can see not just what’s happening, but where the actual opportunity is?

Tommy Vacek: I think everything changes. Most nonprofit teams are drowning in an immense amount of data. The lack of data is not the problem. The direction on where to go with that data is the most important thing. You know when a donor gave last, because you can look that up. You know when someone lapsed. You know when a major gift portfolio has gaps because you don’t have those relationships tied up. But knowing what happened doesn’t tell you what to do next.

Penny helps you make that shift. When you can see what the opportunity actually is, you stop reacting and start leading. Imagine walking into a Monday morning knowing exactly who you have to call and why today is the right moment to call them. Then you know what to say when you get on the phone. You have the context of that individual, what they’ve meant to your organization, what they’ve done for it. So you’re not just managing a spreadsheet, you’re running a strategy.

The best fundraisers have always had this instinct, and Penny gives it to everyone on your team every single day. It’s backed by the data and by our expert playbooks. It’s not a gut feel, and it gives you the confidence to make those decisions much faster rather than just reacting.

Katie Gaston: Everything you shared there is spot on. Next, we’ll look at how Penny helps you focus on the right donors, so you’re not just understanding what’s happening but where to make the biggest impact.

I’m still looking through the chat, and we do have the Q&A section, but I want to clarify something. A lot of you are asking whether there’s a prompt guide so you know the best way to prompt Penny. We have a lot of resources. I’m sure someone on the back end can put it in the chat. We have an AI prompt guide you can use with Penny or another tool if you’re starting your AI nonprofit journey. And by the end of the week, we’re going to have a use case library built out to help you visualize real examples of what Penny can do for your nonprofit. We’ll put the first one in the chat and send the other later.

Now, after you’ve gotten started in a nonprofit and you understand what to do, how do you find the right person to focus on? How do you decide where to focus your time? Let’s get some feedback. What’s hardest about deciding where to focus your fundraising time today? Either put it in the chat or in the poll. Do you not have enough time to think about prioritizing? Maybe you have too much data to review, or it’s not organized. Maybe your board and stakeholders think you should be doing something different, or you’re a small team. If none of those relate to you, put something else in the chat.

So many projects, not enough organized data. “I don’t know my data well enough.” Yes, Megan, that’s a real challenge. Again, fairly evenly split. Time is a challenge. Too much data. And a lot of you are a small team, so literally having someone to validate would be super valuable. A hundred percent, thank you. Let’s hear from Jake on our sales team. He’s going to walk through how Penny can help you decide which donor to focus on, and when.

Jake d’Fonseca: Hi, I’m Jake, an account executive at Bloomerang. When you’re ready to focus on your gifts, you don’t want assumptions. You want data-backed confidence. Here’s what I’d ask Penny when deciding where to focus first with major gifts: “Which donors should we be prioritizing for major gifts right now?”

Penny analyzes real donor data, giving history, engagement signals, recency, and loyalty, to surface donors who are most likely ready for major gift outreach. What makes this powerful is that Penny explains why these donors rise to the top, not just who they are. In this response, Penny highlights donors with high lifetime giving, donors who have demonstrated capacity in the past, and donors whose recent giving patterns suggest they may be ready or overdue for a deeper conversation.

Penny doesn’t just focus on current major donors. She also flags donors who may have given less recently but still show strong potential for larger gifts with the right outreach. That’s critical for retention and reactivation, not just acquisition. From there, Penny helps organize these prospects into meaningful groups so your outreach reflects readiness and capacity instead of treating everyone the same.

Katie Gaston: One of the things I love in that clip is how Penny, as Jake says, doesn’t just tell you who to focus on but explains the why. You can learn a lot from the reasoning behind the information. Tommy, what’s the power of not just being given a list, but seeing the logic that led to that list?

Tommy Vacek: The difference is that you’re actually going to use the list when you understand how it was constructed and why. We all have lists. We have spreadsheets everywhere. You have lists of all your fundraisers’ giving history all time. You have your top donors by giving level. You have lapsed donors from the last twelve months. You have contacts who haven’t been touched in ninety days. Oftentimes those lists just sit there because they don’t have the context of what to do next. You really need a fundraising partner to give you confidence to act on them, especially given the density of the data.

So when Penny tells you to reach out to a specific donor, she tells you why. This is a person who gave consistently for four years and then stopped. This donor just hit a threshold that suggests they’re ready for a bigger conversation. This relationship hasn’t had a meaningful touchpoint in eight months, and they’re at risk. The reasoning changes everything. It turns a name on a list into a conversation you feel prepared to have. It replaces second-guessing with confidence, and it means your team isn’t just working harder, they’re working with intention.

The reasoning is also how you build trust in a tool over time. When a fundraiser sees that Penny’s logic matches their own instincts, or teaches them something they didn’t know, they’re going to lean in more. That’s why it’s so important that Penny tells you exactly why. That’s when Penny stops being a feature and starts being how your team actually operates day to day.

Katie Gaston: I love that. The other power of the reasoning, especially if you’re a new fundraiser or getting to know the data, as I saw in the chat, is that because Penny explains the reason, you really understand what’s happening. The next time you go to make a decision, you have the context you need. Maybe you don’t ask Penny. Maybe you say, “I’ve learned a lot from the last prompts I walked through with Penny, and I’m good to move in this direction.” Thanks for walking through that.

The next step in that logical flow is this: you’re new, you’ve found the right donor, and now you’re about to go into a meeting. You want to make sure the ask, or at least the relationship building in that meeting, is as strong as it can be. When you’re preparing for a conversation with a strategic donor, what gives you the biggest concern or pause today? Answer that poll, and if you have a story, put it in the chat. Is it asking the right amount, timing it correctly, their capacity to give? A hundred percent, Nick. What if they say no? All of the above. I should have added that option. Timing, right amount, what matters most to them. All of those things are really challenging.

The top two answers are: Do I know what matters most to them? And am I asking the right amount? Those are really important questions, and having support going into that conversation as prepared as possible would be ideal. Let’s hear from Dan on our team, who will walk through what Penny can do to support you as you prepare for a donor meeting.

Dan Berkiel: Hi, I’m Dan, a fundraising solutions manager at Bloomerang. Major gifts are built on relationships, and every donor conversation deserves preparation. So before a meeting, this is what I would ask Penny: “I’d like to meet with one of our major donors this month. Can you help me prepare for this meeting with a donor from our most critical group?”

One of the most valuable parts of this response is that Penny helps you avoid common mistakes. Instead of rushing into an ask, she encourages listening, gratitude, and understanding what might have changed. Penny helps nonprofit fundraisers turn donor data into clarity, confidence, and action.

Katie Gaston: Okay, Tommy. If all fundraisers had this level of clarity in preparation before they walked into donor meetings, what do you think that would change about fundraising?

Tommy Vacek: I really think it changes what’s possible for the entire sector. There’s an enormous amount of untapped fundraising potential, and it’s not because anybody is doing anything wrong. It’s about time and strategy. It takes a lot of energy to be intentional with those things, and Penny starts to tear down that barrier. You can make up some of the time by having Penny do some work for you and build a strategy for you.

Fundraisers are stretched really thin, so it’s very easy for a major donor to slip through the cracks. It’s very easy for a mid-level donor who’s ready to upgrade to never get that call. When you multiply that across thousands of nonprofits, we’re talking about millions and billions of dollars in this space that just never happen. It’s not because your cause wasn’t worthy. It’s because the team didn’t have the tools and didn’t see the opportunity.

So when every fundraiser shows up prepared, and I love the example Dan gave us, with every outreach being intentional, no donor falls through the cracks and no context gets missed in that conversation. Retention goes up. Major gifts get made. Mid-level donors feel seen for the first time and start to move up the ladder in their donor life cycle with you.

But the real answer isn’t just a revenue number. It’s what that revenue does. More kids get served by organizations. More communities are supported. More missions get fully funded instead of constantly running on fumes. That’s what you can expect when you start to use Penny. It’s not just a productivity tool. It’s a force multiplier for impact. If we can put that in the hands of every single development team, regardless of size, that is genuinely a different world for the nonprofit sector.

Katie Gaston: So it not only unlocks more fundraising capability but ultimately more good in the world, which is fantastic. We have one more clip to share, and then we’ll walk through some different ways you can use Penny in your nonprofit. I’m excited to talk about how one Bloomerang customer experienced Penny firsthand and the difference she made for their nonprofit. Let’s hear from Joe Nuxhall Miracle League Fields.

Tyler Bradshaw: Every day when I wake up, I think about the special needs athletes we serve. I think about the fact that if not for the Joe Nuxhall Miracle League Fields, what would these individuals be doing on a Friday night or a Saturday morning?

I do trust Penny, and I didn’t expect to coming into this. I was nervous that it would be like every other AI chatbot I’ve ever interacted with. We were lucky enough to connect with the Hatton Foundation in Cincinnati. They’ve been longtime supporters of ours, and they offered us a one million dollar matching gift. They wanted us to raise that money by the end of the year, and nobody was counting, but that was sixty-eight days. The goal was to raise a million dollars toward that match, and we actually raised one point two five million.

For me, as a team of one, having Penny was like adding an additional member to the team. She gave us the ability to say, “We want to talk to ten people over the next month who could make a major gift that will be game-changing for our mission. Who are those ten people, and why?” Penny was able to show us the back-end work on why those people were in that top ten list and what we could talk about to cultivate that relationship and extend it even further. It was a huge help in deciding who that pool of people could be to help us move toward a big goal. It gives our donors a level of confidence that when they donate, they’re giving their best to help us make the best happen for these special needs athletes.

Katie Gaston: We heard from Tyler at one of our meetings recently, and I think he caught many of us, if not close to tears, then pretty meaningfully near it. Tommy, what are your thoughts on the impact Penny was able to make? Did we lose you at time?

Tommy Vacek: Oh, no. Sorry, I did have a blip. Was that the question about the customer?

Katie Gaston: Yes. I know he had presented at our company meeting recently, so I wanted your thoughts on that.

Tommy Vacek: Yeah. When Tyler came and spoke about what he’s doing, we were completely amazed. I think half of our company was in tears by the end of him talking, with the passion and excitement he brought. What was interesting too is that he fully admitted he was a skeptic early on with using Penny, and then he started jumping in and experimenting. Not just meeting a million dollar match but exceeding it is quite amazing. Penny helped drive that strategy, especially under a short deadline. She told Tyler exactly who to reach out to and how to engage with them. It’s a massive success story, and I think we’re going to see more and more people find that same success with Penny. So I encourage you to start throwing some of your hardest problems at Penny and see how she responds.

Katie Gaston: A hundred percent. That’s a great transition. I know a lot of you are asking excellent questions. We’ll get to as many as we can, so keep putting them in the chat and the Q&A. If we don’t get to them in this webinar, we’ll follow up afterward, so feel confident we’ll get to all of them, whether it’s now or later.

Let’s look at our final slide, which shows some other things you could do with Penny. We’ve gone through just three today, but the possibilities are endless. Tyler talked about finding donors for matching gifts. I mentioned cleaning up donor data, like all capitals on one name or lowercase on another, or cleaning up addresses. There’s a lot you can do with Penny automatically to clean up a messy database. You can build unique donor lists. You can prepare board meeting reports. That’s a use case we hear consistently from nonprofits who say, “I’m running into a board meeting. Help me understand our performance for the last month,” and Penny puts together a comprehensive snapshot of exactly what’s happened.

You can build targeted appeal strategies, like which donors to upgrade. And I love this one: how do I grow? A lot of you said you’re a one-man or one-woman team. How do I grow my database and find new supporters? Penny can create a profile of your most engaged donors, and then you can figure out how to find more donors just like them.

Tommy, before we trigger our final poll, in your experience, which use cases do you think will make the biggest difference for fundraisers?

Tommy Vacek: There are quite a few, but if I pull a few off the top: when you think about prioritizing your day, Penny will help you understand where your highest-leverage points are. You have a long constituent list and a long list of relationships to build. Penny will help you understand who to contact that day and give you the context around each of them to confidently reach out and have a meaningful conversation. Building and strengthening your relationships with your donors is absolutely one of the most important things you can do with Penny.

Then you can dive deeper and build a lapse prevention strategy. Penny can identify donors who are starting to show early signs of disengagement before they’re fully gone, help you segment them, build them into groups, and craft campaigns to reach out to them. You’re not having to save a relationship or reacquire one after it’s already lost.

The third piece is donor movement. Donors have different cycles with every nonprofit. We see a lot of donors who start off by volunteering, and as their engagement grows over time, they stay committed as volunteers but you start to foster that into more of a financial ask. You can turn a lot of volunteers into regular recurring donors, and some of those will turn into larger donors. Helping you with that kind of moves management is another area where Penny is really great.

Katie Gaston: I saw some answers come in: “I’d focus on bigger donor asks,” or “I’d spend less time fighting the data and more time building relationships.” A hundred percent, that’s a lot of the reason we built Penny. If something Tommy said, or something on that slide, like cleaning up donor data or finding donors for matching gifts, excites you, put it in the chat. Then we’ll trigger our final poll and get to your questions with the remaining time.

If you want to see what this looks like with your own donors, your own data, and your own questions, we’d love to show you. The best way is to request a demo of the Bloomerang Giving platform if you’re not currently a customer. If you are a customer and want to explore more about Penny or get connected with someone on our team, let us know in the poll or the chat.

Let’s work through some of these questions. There’s a lot in the chat, so I’ll start with some of the open ones in the Q&A. We covered add-on versus subscription. Tommy, we had some questions about which AI partner we’re using on the back end. Do you want to speak to that?

Tommy Vacek: Yes. Today, all of this is part of our third-party processors that we have public, and it will change over time. A lot of it is our commitment to picking the best vendor, the most efficient around token usage. We know many organizations are focused on the environment and making sure we’re doing the right things in that space. So we look at strong commitments from each vendor around what they’re doing for the environment and what they’re doing to offset some of their energy and water usage, and we build a lot of our decisions on that. Today we’re using Anthropic as our main provider. We look at their products, their safety, their environmental stances, and how much we can trust our vendor. That’s why we made our initial choices, and it’s something we’ll continue to evaluate as Penny evolves.

Katie Gaston: That’s super helpful. There were also some questions about reporting. Can Penny help me create a report? Can she create charts? We have some of that in Penny. Do you want to talk through what AI around reporting might look like in Bloomerang?

Tommy Vacek: There are a few pieces to this. If you want to ask Penny for information about your donors, she can pull a lot of insights and calculations about them. Penny has been trained really well on how to do calculations, which AI is not great at out of the box. AI is very probabilistic, so we’ve spent a lot of time making Penny very deterministic in how she provides calculations.

One thing that’s right around the corner is that we’re going to make Penny available inside our report screen. A lot of people love or hate our reports, depending on how your brain works, because of the complexity of the conditional logic in how you set filters and other things. Penny will get to the point of helping you generate those reports so you’re not having to click the right columns and the right filters. We’re hard at work on that, and it’s right around the corner.

Katie Gaston: Amazing. A few chat questions asked about a live demo of Penny. A few options for you. Option one: we’re planning a group training course for Bloomerang customers on Penny in the next couple of weeks. If you aren’t signed up for Bloomerang Learning, I highly encourage it. We have in-app education where you can learn things like Penny, as well as everything else in the Bloomerang platform, through e-learning, and we have weekly group trainings. In addition, if you’re interested in a live demo of Penny and you’re not a Bloomerang customer, let us know. We’re happy to set you up with a quick conversation with someone on our team who can walk you through everything you need to know, as part of a broader conversation specific to your needs.

One of the other questions was whether Penny can reference donor engagement level and generosity through something like DonorSearch or Windfall.

Tommy Vacek: Today, Penny does not have access to something like the DonorSearch generosity score, but that’s probably going to change in the near future. We know it’s something that’s available in reports. Penny is evolving very rapidly, so it’s important to stay in touch with what we’re releasing from a product marketing perspective, because what’s available in Penny changes every week. We’ve heard that this is an important field for those who rely on the generosity score from DonorSearch, so it’s something we’re definitely looking at adding to Penny’s intelligence.

Katie Gaston: That’s a really good call-out. Penny is in beta right now, and we’ve already massively improved a lot based on what we’re hearing from customers and use case needs. One question was, if there’s an issue with Penny, how do you all know? And how do we continue to improve Penny? Do you want to speak to how we hear suggestions and the work we’re doing to keep investing in features like Penny?

Tommy Vacek: Absolutely. With an evolving product, we’ve moved really fast to make Penny available to every single customer, but we’ve tried to balance that along the way. We have a team constantly monitoring error rates and hallucinations and putting in better guardrails to protect the type of responses you get from Penny. That’s going to continue to improve. Almost everything you ask Penny about your core donor data, your constituents, and your transactions, Penny has been worked with, so she can calculate those appropriately and give you back the right information. Those error rates have dramatically gone down as we’ve continued to evolve Penny. Our commitment is to keep making Penny a high-quality product through the beta phase and beyond.

I also saw a question about whether Penny has access to custom fields. Yes, she does, which is really great. As you add key data points to those custom fields, we identified early on that you’re putting valuable data in there, and Penny should be able to access and use it.

Katie Gaston: I think we just have time for a couple more. Tommy, you spoke a little about monitoring for hallucinations, but there was some concern about hallucination with AI. Can you speak to that more, and how we’ve seen Penny improve?

Tommy Vacek: Great question. I think we’ve all used a public LLM, gotten an answer back, and known something wasn’t quite right. It doesn’t feel right, or the AI is making something up. There’s a concept called guardrails that you put inside AI, where you protect against the way it responds to certain questions, and a lot of that is about not making up answers. We’ve calibrated it so that if Penny doesn’t know the answer, she tells you she doesn’t know. That’s a much better experience than what you sometimes get from a public LLM, where you just get an answer back and can’t trust it because you don’t know if it’s right. We really erred on the side of protecting you with the right guardrails, so that if we can’t confidently give you an answer, we let you know.

We’re also monitoring the situations where Penny can’t confidently give you an answer today and prioritizing those. If one’s been asked a number of times, we work on it and build it into Penny in the next iteration. Those are good things to monitor so we can continue to improve Penny.

Katie Gaston: Maybe one more. I know we’re about at time, but there was also chat earlier about environmental impact, which comes up a lot in conversations about AI models. You spoke a little about how we thought about which partner to work with. Is there any other feedback you want to provide on how we’re thinking about the impact on the environment?

Tommy, I lost your audio.

Tommy Vacek: There we go. Thank you. It’s something we’re going to continue to monitor. It’s changing really fast how models are being created. Every time you turn around, there’s a new model being released, and every model is completely different. You have to do the research and talk to your vendors to understand where some of them are strong. One thing we’ve looked at is that even inside the big providers, you have multiple different sets of models that are completely different from an efficiency standpoint and from a deep research standpoint. You shouldn’t use the same model for every single task. So we’ve taken the approach that certain types of tasks should use different types of models, based on the complexity, so we can be as efficient as possible when using Penny.

Katie Gaston: Thanks so much, Tommy. I know that was a conversation that came up in the chat. I appreciate everyone’s questions. We’re at time, so thank you all for taking the last forty-five minutes to walk through this with us. If we didn’t get to your question today, we’ll be following up, likely by the end of the week, with more information. Watch for the recording in your email tomorrow, and if you weren’t able to attend, you’ll be watching this in the recording. Thank you so much, Tommy, for sharing your expertise. I hope you all have a great rest of your afternoon.

Tommy Vacek: Thanks. Thank you all.

Katie Gaston: Bye.

Key takeaways:

  • Penny is an AI fundraising assistant built directly into the Bloomerang Giving platform. Fundraisers can ask questions in everyday language and get answers grounded in their own donor data. Penny's guidance is shaped by playbooks drawn from thousands of Bloomerang consulting wins.
  • Penny explains why she recommends a donor, not just who. Her reasoning, such as a donor who gave for four years and then stopped, turns a name on a list into a conversation fundraisers feel prepared to have. It also helps newer fundraisers learn the data.
  • Privacy and trust are built into how Penny works. Bloomerang uses enterprise agreements with its AI partners, with contractual protections that no customer data is used to train public models. Anthropic is the main provider today.
  • One Bloomerang customer used Penny to exceed a $1 million matching gift in 68 days. As a team of one, they asked Penny to identify ten likely major gift prospects and why. They raised $1.25 million.
  • Penny is in beta and free for every Bloomerang CRM customer for now. Guardrails make Penny say when she doesn't know an answer, and she can access custom fields. Help with building reports is coming soon.
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