Fundraising in an AI-Driven World: Balancing Tech with Personal Connection

Chapter Leadership Brief 2.7.25

by Mike Esposito, CFRE
 Founder and Lead Fundraising Strategist, Mike Esposito Fundraising

AI is revolutionizing fundraising—enhancing donor research, automating personalized communications, and streamlining operations. But does increased automation risk losing the human connection that makes philanthropy so powerful? The key is finding the balance—leveraging AI’s efficiency while preserving authentic donor relationships.

Over the holidays, I binged episodes of The Office. One in particular stood out: the one where Michael Scott drives his car into a lake. Why? A GPS told him to.

The whole episode is a hilarious and at times poignant exploration of humans adapting to new technology. Ryan insists that a new website will save Dunder Mifflin. Michael is convinced that hand-delivering elaborate gift baskets will win back lost customers. Neither is wrong. In the end, though, it turns out that neither approach works very well without the other.

We are at a similar moment with the use of AI in fundraising.  Personalization and stewardship build authentic relationships and nurture donor trust. But without a solid tech stack—your website, CRM, and AI tools—you’re limiting your growth potential. The key? Balance.

Too many changes at once overwhelm teams and donors (not unlike the Dunder Mifflin team struggling to figure out their Blackberries). Too little innovation leaves money on the table (like Dunder Mifflin’s lost customers, who have switched vendors because of a competitor’s lower prices and functional website). But with a thoughtful balance fundraisers can empower their teams with AI without losing the personal connections that inspire generosity and long-term support.

AI’s Growing Role in Fundraising

AI-driven tools are transforming how fundraisers identify prospects, engage donors, and manage operations. AI-powered research tools like Hatch and DonorSearch can analyze donor wealth indicators, giving history, and social media engagement faster than any human team. Chatbots, AI-generated emails, and predictive analytics enable hyper-personalized donor interactions tailored to donor behavior and interests. Generative AI tools like ChatGPT and Claude streamline proposal writing and impact reports and fine-tune communications, freeing up time for relationship-building.

Some organizations are even experimenting with AI-driven donor engagement. Version2.ai, the first AI R&D lab focused on nonprofit fundraising, has introduced Virtual Engagement Officers (VEOs) that autonomously manage donor portfolios. These AI-driven officers look and sound like real people (although they clearly identify themselves as AI) and they can identify, qualify, engage, solicit, and steward donors—all with minimal human intervention.

This can be both exhilarating and terrifying– today’s version of Dunder Mifflin employees considering if they can work at a website-driven business (!). The potential to increase efficiency, expand reach, and scale donor engagement is thrilling. A fundraising shop of one suddenly has the tools to do the work of three people. But as AI takes on a larger role in fundraising, it’s worth asking: What do we risk when we rely too much on automation? And are we about to drive the car into the lake?

The Risks of Over-Reliance on AI

AI offers incredible efficiencies, but nonprofits should consider its potential drawbacks. Too much automation in communication can feel impersonal, which can erode our relationships with donors over time. After all, it is the contents of that email that matter most, not an optimized email cadence. Our best supporters still value face-to-face engagement and authentic connection. Fundraising is about trust, and AI alone can’t cultivate that trust.

On the predictive side, AI-driven wealth screening may reinforce bias in donor targeting, prioritizing certain demographics while overlooking others. And we risk losing grasp of our own strategy when we uncritically outsource that work to an AI tool, reengaging only when the work is done.

If we don’t take the time to learn to work with AI, and to train our teams to do it ethically, honestly, and well, we risk using the technology about as well as Michael and Dwight used the GPS– which in their case caused an expensive, embarrassing mistake and ultimately alienated a potential client.

Finding the Right Balance

So how can fundraisers harness AI without losing the human touch?

1. Let AI lead in the insights, but manage the relationship yourself.  AI can identify high-potential donors, but fundraisers should still cultivate relationships personally. The best results come from AI-assisted research paired with human engagement.
    
2. Automate administrative tasks—but keep key conversations personal. AI can handle email segmentation, impact reporting, and data analysis, but please take the time to have that conversation with the donor yourself, in person, via Zoom, on the phone. Even if those meetings still make you nervous, that is real and human, and your donors value that.
    
3. Be prepared to be transparent with donors about AI’s role. Letting donors know how AI is being used fosters trust and ensures alignment with ethical fundraising principles.
    
4. Train fundraising teams to integrate AI thoughtfully, and be patient with their objections and their individual learning styles. AI is most effective when it is enhancing our strengths, not just compensating for our weaknesses.

After all, your donors give to help solve a problem, or help people– not as a reaction to some calculated activity. 

The Future of AI in Fundraising

To talk about the future of AI in fundraising, we can do worse than return to Scranton. While Ryan’s aggressive push for modernization is not wrong, his posturing and lack of empathy are alienating to the very people he is trying to help. Yet Michael’s typically over-the-top reaction ultimately yields the insight that, while everybody likes a good chocolate turtle, customers also want the efficiency of a functioning website.

Similarly, the communities we serve, and the donors who sustain them, do not want nonprofits replaced by artificial intelligence. They want authentic relationships based on shared values, because people give to people, not to algorithms. But, like Dunder Mifflin’s lost customers, they do want to see their chosen nonprofits using the tools that will make them efficient and effective. It’s not about technology versus human beings, but about people using technology thoughtfully as a tool that can help all of us.

References
Daniels, G. (Writer), & Kwapis, K. (Director). (2007). Dunder Mifflin Infinity: Parts 1 & 2 (Season 4, Episodes 3 & 4) [Television series episode]. In G. Daniels (Executive Producer), The Office (U.S.). NBC.

Mike is the founder and lead fundraising strategist of Mike Esposito Fundraising, a consultancy dedicated to helping small to midsize nonprofits strengthen donor relationships and achieve long-term fundraising success through coaching, fundraising assessments, and campaign support. A CFRE-certified strategist, mentor, and coach, Mike partners with organizations to develop tailored solutions that align with their mission and goals. His expertise spans fundraising strategy development, major gifts, donor stewardship, campaigns, and board and staff coaching—offering nonprofits the tools and guidance they need to build sustainable, high-impact fundraising programs.