Nonprofit Nation with Julia Campbell

Episode: How AI Can Help Year-End Fundraising Overwhelm

Guest: Tommy Vacek, CTO at Bloomerang
Date: November 10, 2025

Episode Overview

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.

Key Discussion Points & Insights

1. The Reality of Year-End Fundraising Stress

• Fundraising Crunch: Nonprofits typically raise 30–40% (or more) of their annual donations in December, creating intensely stressful weeks for teams already stretched thin.
• Trade-offs: Fundraisers often must decide between investing time in major donor relationships or broader campaign strategy, which creates "opportunity costs" during this high-stakes season.
  • Quote (Tommy Vacek, 05:33):

    "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."

2. AI’s Direct Applications for Fundraisers

[09:37] Tommy discusses three key AI leverage points:

• Donor Segmentation:
  • Automates breaking up constituents by their journey, donation history, engagement, etc.
  • Moves the process from days to mere minutes.
  • Caution: Never upload sensitive donor data to public AI models; anonymize if necessary.
  • Quote (Tommy Vacek, 11:15):

    "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."

• Copywriting and Appeals:
  • AI can generate tailored campaign messages for different donor segments.
  • Penned appeals are more relevant, timely, and can be deeply personalized if connected to CRM data.
  • Quote (Tommy Vacek, 13:00):

    "Imagine saving a day or two during this critical season. That’s a huge win."

• Stewardship and Thank You's:
  • AI helps with message planning (“What and when to say”) and enables personalized touches at scale.
  • Bloomerang has built-in tools for video acknowledgments to add a human element.
  • Quote (Julia, 15:40):

    "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."

3. Benefits of Personalization at Scale

• Even small gestures can make a nonprofit’s outreach stand out in crowded inboxes.
• Personal touches (e.g., referencing donor’s past contributions or recent trips) foster loyalty and higher response rates.
  • Quote (Tommy Vacek, 18:22):

    "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."

4. Building AI Skills for Nonprofit Professionals

• The importance of practice: Start small, experiment, and treat AI as a “thought partner” rather than a magic solution.
• Prompting: Learn how to craft better instructions and iterate for improved outputs.
  • Quote (Tommy Vacek, 19:31):

    "Your better input is going to produce a better output...Treat it as a colleague that you’re interacting with."

• Develop basic understanding of privacy, accuracy, transparency, and environmental impact of AI tools.
  • Not all AI models—or vendors—are alike; do homework before trusting sensitive data.

5. Ethical & Environmental Considerations

[24:06]

• Julia and Tommy stress the need for nonprofits to evaluate the ethical implications of any tool, including but not limited to AI (e.g., privacy, environmental footprint, vendor ethics).
  • Quote (Julia, 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?"

Deep Dive: Bloomerang’s AI Tool “Penny”

What Sets Penny Apart

• Combines three pillars: AI, your unique data, and Bloomerang’s accumulated nonprofit expertise (“playbooks” developed from direct consulting).
• Goes beyond surface-level chatbots by offering tailored recommendations for lapsed donors, recurring giving campaigns, and even board communication.
  • Quote (Tommy Vacek, 26:42):

    "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."

• Penny can help with campaign strategy, donor engagement, board updates (even the delicate “ask board to give”).
  • [30:22] Memorable Use Case:
    • Penny helps executive directors draft kind, direct requests for board giving—an often awkward task.

The Creation of Penny

• Name inspiration: Project started as “Pennyworth” (Batman’s butler Alfred), evolved into Penny to reflect the nonprofit world’s strong female leadership and positive, supportive energy.
  • Quote (Tommy Vacek, 34:39):

    "We felt it was incredibly important to have a female persona with the AI chatbot...Penny just really stuck."

Practical Advice & Memorable Quotes

Approaching AI: "Take Shots on Goal"

[35:05]

• Start with small, safe experiments; don’t worry about having it all figured out right away.
• Get basic education on how AI tools, vendors, and data agreements work.
  • Quote (Tommy Vacek, 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.”

Standing Out in Year-End Appeals

• Quote (Julia, 15:40):

  "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.'"

• Quote (Tommy Vacek, 18:12):

  "It doesn’t take much to stand out."

Viewing AI as a Human Assistant

• Use AI as an “executive assistant you don’t have”—to prep for board meetings, think through messaging, or research donor patterns.
• Use it not to replace relationships but to make time for more meaningful human contact.
  • Quote (Julia, 32:14):

    "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."

Important Timestamps

| 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 |

Conclusion

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:

• Start experimenting with AI in small, low-risk ways.
• Focus on personalizing donor communication using tools like Bloomerang or similar.
• Prioritize stewardship and relationship-building with freed-up time.
• Educate yourself on privacy, ethics, and environmental impact before adopting new tools.

Learn more:

• bloomerang.com
• bloomerang.com/blog/meet-penny
• Year-end fundraising checklists: jcsocialmarketing.com/bloomerang
• Nonprofit Social Media Summit: nonprofitsocialmediasummit.com

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?”