Tech, data, and generosity are not abstract buzzwords—they’re concrete levers that can stabilize funding, expand impact, and re-energize exhausted fundraisers. Chief Fundraising Officer Kimberly O’Donnell of Bonterra joins us to map out how recurring giving, trust-based philanthropy, and AI-powered tools can move the entire sector from scarcity thinking into a new “generosity generation.”

Kimberly starts by reframing recurring giving as non-negotiable infrastructure, not a nice-to-have tactic. As she puts it, “Recurring giving is essential for nonprofit sustainability. Just no, hard stop there.” Bonterra’s own research shows why: in its Meet the Moment report, 58% of federally funded nonprofits report financial instability this year. In that environment, a predictable base of sustainers—monthly and annual—can keep programs moving even as federal funds, disaster response dollars, and one-time grants fluctuate.

She shares a compelling case study: a Bonterra client that introduced three choices on its donation page—one-time, monthly, and annual. By normalizing both monthly and annual recurring options, that organization grew from zero sustainers to more than 65,000, proving that donors will enthusiastically choose ongoing support when invited clearly and confidently.

Kimberly also dismantles the common boardroom fear that sustainers will cannibalize major gifts. In her view, that’s simply a myth. Monthly donors should be seen as high-value relationship partners whose lifetime contributions, planned gifts, and sponsorship potential can grow over time. The real problem isn’t “small monthly donors”; it’s organizations deciding on behalf of donors when and how they will give.

From there, the conversation widens. Kimberly explains how Bonterra’s vantage point—serving nonprofits, community foundations, CSR programs, and public agencies across the social good ecosystem—reveals sector-wide patterns in real time. Trust-based philanthropy, she notes, hasn’t disappeared; it’s evolving. Funders are becoming more intentional, concentrating resources on core pillars while streamlining reporting and using their networks to introduce nonprofits to new corporate and philanthropic partners.

Achieving that shift, Kimberly argues, will require data, AI, and human connection working together—what Bonterra calls the generosity generation.

AI, in particular, is already reshaping daily fundraising practice. Bonterra has been using agentic AI since 2016–2017, and its new tools are built with a “human in the loop” philosophy so fundraisers can test, refine, and own their messages.

Kimberly’s closing message is both empathetic and urgent: acknowledging nonprofit exhaustion yet pushing leaders to resist retreat: this is not a moment to slow down—it’s a moment to experiment, ask bolder questions, and lean on tools that make the work more sustainable.

#TheNonprofitShow #NonprofitFundraising #BonterraTech

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Donor love is measurable, and in this lively discussion, guest Lynne Wester, Principal and Founder of Donor Relations Group, brings the receipts. Drawing on data from her seventh global donor relations survey, conducted every two years since 2013 with more than 1,000 participants, Lynne shows us why retention, not the next big campaign, is where the real money is.

Her core message is blunt and refreshing: we obsess over the ask even though it represents a tiny slice of our contact with supporters. As Lynne puts it, “Retention is the secret sauce of fundraising.” Most organizations still pour staff time and budget into events and tactics with weak ROI, while reporting that they are only able to share impact with less than 20 percent of their donors. That gap is not just operational; it is a revenue problem.

The survey findings expose a pattern. Many donor relations teams sit under a mountain of tasks but lack a strategic plan, making them vulnerable to “seagulling” requests that fly in, drop work, and disappear. At the same time, donor relations professionals tend to stay in their roles four to nine years, while frontline fundraisers churn in about 16 months. The people who understand donor experience best often have the quietest internal voice, and Lynne’s work is about giving them data to change that.

She shares how longitudinal data helped the sector mostly abandon donor honor rolls: today, over 80 percent of nonprofits no longer produce donor lists that were costly and not meaningful. The survey is now pushing similar change around giving societies, the split between receipts and acknowledgements, and the use of AI. Lynne is candidly concerned that many organizations use AI tools without organizational policies, even as donor databases at major institutions have been compromised. For her, donor confidentiality and the Donor Bill of Rights demand guardrails before automation.

Perhaps the most poignant remark is Lynne’s insistence that gratitude and listening are not “extras” but performance drivers. Retaining a donor is five to seven times less expensive than acquiring a new one, and organizations that cared for donors as human beings during crises like the 2008 downturn and COVID raised twice as much as those that just kept asking. She argues that if a donor is not “worth a stamp,” the organization does not deserve the gift.

Lynne leaves viewers with a challenge wrapped in encouragement: use data to question tradition, ask donors for their opinions, and treat stewardship as strategic fund management, not a courtesy. When you align technology, policies, and human connection around gratitude and impact, you are not just being nice—you are building a durable, scalable fundraising engine.

#TheNonprofitShow #DonorRelations #FundraisingData

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Who actually owns data protection in a nonprofit? In this fast-paced conversation, host Julia C. Patrick sits down with Taysha Adams, Manager Technology Support at JMT Consulting, and Josh Fricovsky, Engineering Director at Cortavo, to tackle the uncomfortable truth: cybersecurity is no longer “someone else’s job.”

Taysha starts with a reality check: most vulnerabilities don’t begin in a server room. They start with everyday behavior. From checking work email on public Wi-Fi to logging in on a friend’s device, casual habits open doors to attackers. As she explains, “Everybody’s responsible for data security and protection… most vulnerabilities do come in from the end users.” JMT has spent more than a year realigning internal processes, tightening device controls, and partnering with Cortavo so their own team—and their clients—are better shielded.

Josh builds on that by showing how fast the threat landscape is evolving. Cortavo’s job as a managed service provider is to sit on the “bleeding edge”: endpoint protection, email security, MFA, VPNs, and now mobile device management for a workforce that increasingly works on the move. He notes that “the cost of inaction is going to be 10 to 100 times more than” the investment in proactive security. It’s not just about tools; it’s about culture, education, and leadership setting the tone.

The conversation then moves to the devices we use every day. Laptops, tablets, and phones are cheaper and more plentiful than ever, but every extra device is another front door. The guests stress that nonprofits need clear policies for using personal phones for work, along with mobile device management to protect company data without “controlling” the phone itself.

AI takes the discussion to another level. Both guests are enthusiastic users, but they warn that unregulated use is dangerous. Taysha urges organizations to set guardrails and favor licensed or enterprise tools so prompts, donor details, and templates aren’t quietly training public models. Josh goes further, recommending offline or private LLMs for sensitive data and pointing out that attackers are already using AI for sophisticated social engineering, including voice cloning and real-time credential theft.

Finally, the trio frames cybersecurity as a governance and financial issue, not just an IT problem. Data loss can mean lost clients, destroyed reputation, and even the end of an organization. Partnering with firms like JMT and Cortavo, building internal awareness, and treating security like an essential protection policy—not a luxury—are presented as non-negotiable steps for modern nonprofits.

This episode is a must-watch for executives, boards, and staff who touch data in any way—which is everyone.

#TheNonprofitShow #NonprofitCybersecurity #DataProtection

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