Podcast Summary:

Nonprofit Leadership Podcast
Host: Dr. Rob Harter
Episode: The Biggest Fundraising Challenges Facing the Social Impact Sector
Guest: Jenna Lynch, DonorBox
Date: December 22, 2025

Episode Overview

This episode dives deep into the biggest fundraising challenges and trends currently shaping the nonprofit and social impact sector. Dr. Rob Harter hosts Jenna Lynch from DonorBox, who draws upon her experiences working with nonprofits nationwide and attending numerous industry conferences. The discussion unpacks current mindset shifts among nonprofit leaders, explores generational giving differences, tackles the realities of donor retention and fatigue, and dissects the practical versus hype-filled use of AI and technology in fundraising.

Key Discussion Points and Insights

1. Fundraising Trends and "Back to Basics" Mindset

• Shift Away from “Reactive Fundraising”
  Jenna observes a major mindset change in nonprofit leadership:

  “Leaders have collectively decided we can't build our organizational future on reactive fundraising anymore.” (03:42, Jenna)
  Economic fluctuations and unreliable grant cycles have compelled leaders to seek revenue sources they can control.

• Renewed Focus on Individual and Recurring Donors
  Despite buzz about trends or technology, organizations are returning to foundational strategies, particularly by investing in long-term relationships with individual donors and emphasizing recurring donations:

  "Recurring giving is just a major leadership priority this year." (05:33, Jenna)

• Ditching the “Always-On” Approach
  Nonprofits are focusing less on constant outreach (“always-on fundraising") and more on highly intentional, meaningful donor engagements:

  “You’re moving away from how do we send more messages, how can we be the squeaky wheel to how can we create fewer moments, but the ones we do create are even more meaningful?” (06:33, Jenna)

2. Deepening Donor Engagement & Retention

• Personalization & Active Listening
  Jenna emphasizes creating specific donor journeys based on segmentation and relationship-building, even if it requires more effort:

  “It’s not about doing less, it's doing what matters most and focusing your efforts around something that will feel meaningful to your community.” (08:45, Jenna)

• Retention is Priority – Especially for First-Year Donors
  Both Dr. Rob and Jenna note that total donor counts are falling even as overall donated dollars remain steady or rise – a risky paradox, making retention critical:

  "We're focusing heavily on the first-year donor experience because that's where the biggest drop off happens." (10:36, Jenna)

• Broadened Engagement Definition
  Not all engagement is monetary; maintaining relationships through storytelling, volunteerism, and community updates helps weather temporary lulls in giving:

  “Someone who isn’t giving financially this year … they're a supporter that might just be navigating a tough season." (11:14, Jenna)

3. Millennials and Gen Z: Changing the Giving Landscape

• Intentional & Relational Givers
  Millennials and Gen Z demand transparency, alignment with values, and active participation, not just transactional donations:

  "We, the millennials, we don't give impulsively. We give intentionally. We want clarity, we want the full story, and we want alignment." (12:49, Jenna)

• Community & Co-Creation
  Younger donors seek authentic invitations into community, often favoring advocacy and volunteering alongside donations:

  “They don’t want to just give a gift and walk away. They want to volunteer, want to advocate more…They want that community experience.” (13:55, Jenna)

• Preparing for the Generational Wealth Transfer
  The sector needs to engage these groups now, as massive wealth shifts from Boomers will empower Millennials and Gen Z to make major giving decisions:

  “Now’s the time to start planting seeds…Framing it about legacy and values.” (15:30, Jenna)

4. Donor Fatigue—Reality or Misdiagnosis?

• Donor Fatigue Often Misunderstood
  Jenna argues that so-called “donor fatigue” is frequently just disengagement caused by lack of meaningful connection, not exhaustion from giving:

  “I don’t think donors are tired of giving. I think they’re tired of giving without understanding the meaning behind it. Plain as that.” (18:44, Jenna)

• The Power of Transparent, Honest Communication
  Regular updates—especially genuine, unpolished progress reports (not just success stories)—keep donors feeling involved and appreciated:

  “Some of my favorite emails are all lowercase, you know, stream of consciousness…It’s not that polished…it's the, here's what went well this month, here's what surprised us, here's what we're adjusting, here's where you fit into this picture. And donors love that.” (19:58, Jenna)

• An Important Warning

  “Silence creates doubt.” (23:32, Jenna)
  Even when there isn’t good news, say something.

• Multiple Engagement Options Sustain Commitment
  When donors can’t give financially, offering them other ways to participate (volunteering, sharing, feedback) retains their connection.

5. AI and Technology: Practical Applications, Not a Panacea

• From Hype to Grounded Use
  The sector has moved past “will AI replace fundraisers?” to “how can AI free up time for our teams to do more human, relational work?”

  "AI is becoming that quiet, behind-the-scenes partner that just takes work off of people's plates…It's not work away from them necessarily.” (25:07, Jenna)

• AI for Efficiency, Not Relationship-Building
  Common ways AI is helping:

  • Cleaning donor data
  • Spotting giving patterns
  • Drafting reports and correspondence
  • Automating thank-yous and reminders

  “What donors feel…isn’t the AI, right. They feel the results of it.” (26:13, Jenna)

• Practical Investment and Security
  For low-budget orgs, Jenna recommends using built-in AI tools within secure CRM platforms, rather than uploading sensitive info to public AI tools:

  “If you are using ChatGPT or Gemini, do not upload your donor lists into those systems…That is not safe. It is not ethical.” (29:09, Jenna)

• AI Tools: Free and “Worth It” Only If Secure

  "I have never paid for an AI tool…If you are using a CRM that has a built-in AI assistant, worth it." (28:44, Jenna)

Notable Quotes and Memorable Moments

• On donor relationships:

  “If you want it to be sustainable, you give it your all, especially at the beginning.” (10:43, Jenna)

• On the need for candor in communications:

  “Some organizations make the mistake of…‘we don't have anything good to update on’…So they don't communicate, and silence creates doubt.” (22:52, Jenna)

• On blending technology and humanity:

  “AI… just clears the path for [relationships].” (27:02, Jenna)

• On legacy and futureproofing:

  “Now's the time to start planting seeds…framing it about legacy and values." (15:30, Jenna)

Timestamps for Key Segments

• Trends in Fundraising & Return to Basics – 03:42–07:50
• Making Donor Moments More Meaningful – 08:03–09:13
• Donor Retention & Engagement Strategies – 09:13–12:04
• Millennials and Gen Z Giving Patterns – 12:04–15:15
• Legacy Giving and Wealth Transfer – 15:15–16:37
• Donor Fatigue Reconsidered – 17:47–23:32
• Silence Creates Doubt – 23:32–23:37
• AI in Nonprofits: Practical Uses – 25:04–30:35
• Security Warning on Public AI Tools – 29:09–29:11

Tone and Language

Throughout the episode, the tone is conversational, candid, and highly practical. Jenna and Dr. Rob blend warmth and expertise, offering honest, often reassuring perspectives with a touch of humor and personal experience.

Final Recommendations

Jenna underscores the importance of:

• Investing in recurring giving and individual donor relationships
• Prioritizing authenticity and ongoing, honest communication
• Broadening the definition of engagement
• Using AI and automation thoughtfully—always safeguarding donor data!

For further resources, Jenna recommends visiting the DonorBox website for free educational materials, blogs, and podcast episodes.

A succinct takeaway:

Nonprofit fundraising’s future isn’t in chasing shiny new trends, but in deepening genuine relationships, modernizing mindfully, and communicating with candor—while letting technology do the heavy lifting on the backend.