What the Fundraising 288: Delusion, Disruption, and the Future of Fundraising Systems with Natalie Poindexter
Sometimes the most meaningful innovations begin with frustration. In this conversation, Natalie Poindexter shares how questioning broken systems, both in nonprofit funding and in technology, led her to build new solutions designed with empathy, accessibility, and human support at their core.
Natalie, a former grant writer turned funding systems architect and consultant, explains how her career evolved into helping nonprofits design stronger funding infrastructures. Acting as a "fractional development department," she supports organizations by building sustainable programs and processes. She also introduces Scaffina, a technology platform created by women for women that simplifies complex funding workflows, reducing burnout among development directors and grant writers.
Throughout the discussion, Natalie explores the deeper motivations behind building technology for social impact. Natalie reflects on a pivotal moment at South by Southwest, where she challenged a U.S. SBA administrator about gaps in support for procurement and entrepreneurs. That moment reinforced her belief that meaningful change often requires challenging existing systems. The conversation also touches on the importance of human-centered technology, combining AI tools with real guidance and support. Natalie candidly discusses the barriers women, especially women of color, face in the tech ecosystem.
In this episode, you will be able to:
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Understand how funding systems can be redesigned to better support nonprofit organizations.
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Recognize the importance of combining AI tools with human guidance in social impact work.
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Gain insights into the challenges women, particularly women of color, face in the technology and funding ecosystem.
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Explore how questioning existing systems can lead to innovative solutions.
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Learn the value of supportive communities and self-care in sustaining long-term impact and entrepreneurship.
Get all the resources from today’s episode here.
Support for this show is brought to you by Practivated. Practivated delivers AI-powered donor conversation simulations that let fundraisers practice in a private, judgment‑free space—building confidence, refining messaging, and improving outcomes before the real conversation even begins. Developed by fundraising experts with real‑time coaching at its core, it’s the smart way to walk into every donor interaction calm, prepared, and ready to connect. Learn more at practivated.com.
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If you’re looking to raise more from the right funders, then you’ll want to check out my Power Partners Formula, a step-by-step approach to identifying the optimal partners for your organization. This free masterclass offers a great starting point.