The Metric Charities Are Missing: Enterprise Value for Non-profits | Anton Lipkanou

Non-profits Need New Funding Models — Here’s Why

In this episode, Chaula Gupta, Vice President and Chief Program Officer at Digital Promise, joins Greg Sobiech to explain how nonprofits can move beyond short-term projects toward sustainable, scalable impact. Chaula explores alternative models like fee-for-service, non-profit/corporate partnerships, and venture-style investing, and explains how AI can shift from incremental efficiency gains to truly transformative learning experiences. Chaula and Greg discuss: - Why project-based funding fails to deliver systems change - How nonprofits can balance big, ambitious ideas with long-term execution - The case for fee-for-service and venture models inside nonprofits - Why adoption matters more than innovation in education technology - How AI can deepen learning, not just save time

Untangling Non-profit Data Chaos: Save the Children’s Omni-Channel Marketing Approach | Jon Wheeler

Jon Wheeler, Senior Director of Direct Marketing at Save the Children US, joins Greg Sobiech for a deep dive into one of the sector’s biggest challenges: how non-profits cut through overwhelming noise and deliver messages donors actually care about. Jon has spent his career at the intersection of digital marketing, data, and donor experience. In this episode, he breaks down how charities can move from siloed channels and a spaghetti mess of data to something far more powerful: a true omni-channel, donor-centric system that gets the right message to the right person at the right time. 👉 Whether you're a non-profit leader, fundraiser, digital marketer, or someone trying to make sense of donor behavior in 2025, this is a must-listen conversation. Jon and Greg discuss: 👉 Why donors tune out, and how to break through 👉 How non-profits can escape siloed channels and think like a “symphony” 👉 The real reason personalization is so maddeningly hard 👉 How AI *might* finally help isolate signal from noise 👉 Why data hygiene still matters in 2025 👉 How donor intent and undesignated revenue collide 👉 The big opportunity (and threat) in today’s giving environment 📌 Chapters: Listen to more Giving Growth episodes: https://delvedeeper.com/podcast/ Connect with Greg Sobiech: https://www.linkedin.com/in/gsobiech/ Connect with Jon Wheeler: https://www.linkedin.com/in/jonwheeler71/ Giving Growth is brought to you by Delve Deeper: https://delvedeeper.com/ 🔔 Subscribe for interviews with nonprofit leaders reshaping the sector.

Why Every Fundraiser Needs a Testing Strategy - Not Just Tech | Ethan Wasserman

Ethan Wasserman, Senior Director of Paid Media at the National Multiple Sclerosis Society, joins Greg Sobiech to talk about the real forces reshaping digital fundraising, and why AI alone won’t save your strategy. With 15+ years leading large-scale digital programs, Ethan brings a rare mix of experimentation discipline, practical data skills, and a deep respect for the human side of giving. In this conversation, Ethan explains how younger donors make decisions, why “experiential giving” is rising, and what nonprofits get wrong about testing and technology. He also shares the surprising lesson he learned from a Google penalty early in his career — and how it shaped the way he approaches marketing today. 👉 Whether you're a non-profit leader, digital fundraiser, or marketer trying to make sense of the AI wave, this episode will help you think sharper, test smarter, and avoid the traps of over-automation. In this episode, we explore: 👉 Why AI is changing fundraising — and what it still *can’t* replace 👉 How to design experiments that actually teach you something 👉 What younger donors really want (it’s not what you think) 👉 Why donor engagement must feel more like an experience, not a transaction 👉 How to use data without becoming dependent on algorithms 👉 The biggest misconception nonprofits have about technology partners Chapters 📌 Links Listen to more Giving Growth episodes: https://delvedeeper.com/podcast/ Connect with Greg Sobiech: https://www.linkedin.com/in/gsobiech/ Connect with Ethan Wasserman: https://www.linkedin.com/in/ethanwasserman/ Giving Growth is brought to you by Delve Deeper: https://delvedeeper.com/ 🔔 Subscribe for regular interviews with nonprofit leaders who are reshaping the not-for-profit world and tackling its challenges head-on.

How Microsoft’s AI Team Is Helping Non-profits Transform | Christina Macchiarola

Technology can feel intimidating for non-profits, but it doesn’t have to be. Christina Macchiarola, Global Experiences and Events Lead at Microsoft Elevate, joins Greg Sobiech to unpack how charities can turn technology, data, and AI into tools that actually advance their mission. Drawing on her experience helping organizations modernize through Microsoft Elevate, Christina shares why successful tech adoption starts with people and storytelling, not software. She explains how breaking down silos between fundraising and IT can transform donor engagement and build stronger, more adaptive organizations. From Make-A-Wish Foundation’s unified data systems to the power of asking donors why they give, Christina shows how tech and empathy can work hand in hand to drive lasting impact. Greg and Christina discuss: 👉 Why people, process, and technology must align for real transformation 👉 How better questions lead to smarter tech investments 👉 What non-profits can learn from political campaigns about engagement 👉 How storytelling connects fundraisers, technologists, and donors 👉 Why investing in infrastructure is essential to keeping missions strong This episode is for non-profit CEOs, CMOs, and digital leaders who want to stop fearing technology — and start using it to deepen connection and accelerate impact. 📌 Chapters: Listen to more Giving Growth episodes: https://delvedeeper.com/podcast/ Connect with Greg Sobiech: https://www.linkedin.com/in/gsobiech/ Connect with Christina Macchiarola: https://www.linkedin.com/in/christina-macchiarola/ Giving Growth is brought to you by Delve Deeper: https://delvedeeper.com/ 🔔 Subscribe for regular interviews with nonprofit leaders who are reshaping the not-for-profit world and tackling its challenges head on.

The Metric Charities Are Missing: Enterprise Value for Non-profits | Anton Lipkanou

Most nonprofit leaders focus on this year’s budget. But what if we started measuring our organizations the way for-profits do — in terms of long-term enterprise value? In this episode, Anton Lipkanou, President at Delve Deeper, joins Greg Sobiech to unpack why charities need their own version of enterprise value. Anton argues that diversification, donor trust, and personalized engagement are what determine whether an organization thrives 30 years from now — or fades away. He shares a practical framework for personalization at scale, including closing donor data gaps, using AI to perfect messaging, and generating short-term surplus that funds long-term stability. In this episode: 👉Why “enterprise value” matters for charities 👉How to measure your donor file like an investor measures a portfolio 👉What diversification really means (beyond demographics) 👉How to personalize at scale using AI and micro-audiences 👉The paradox of long-term vision and short-term results — and how to fix it 👉The one mistake that turns donors away instead of drawing them in 🎯 For non-profit CEOs, CMOs, and fundraising leaders who want to future-proof their organizations and build lasting donor trust. 📌 Chapters: 00:00 - Intro 01:01 - Enterprise value for charities 08:44 - Short-term targets vs long-term thinking 15:40 - Evergreen fundraising and emergency giving 20:56 - Personalization at scale 29:36 - Obstacles to digital fundraising in 2026 36:39 - Step-by-step use of AI for donor segmentation 40:06 - Outro Listen to more Giving Growth episodes: https://delvedeeper.com/podcast/ Connect with Greg Sobiech: https://www.linkedin.com/in/gsobiech/ Connect with Anton Lipkanou: https://www.linkedin.com/in/alipkanou/ Giving Growth is brought to you by Delve Deeper: https://delvedeeper.com/ 🔔 Subscribe for regular interviews with nonprofit leaders who are reshaping the not-for-profit world and tackling its challenges head-on.