Giving Growth

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

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.

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.

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.

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.

In this episode of Giving Growth, we sit down with Richard Kostro, Senior Vice President and Chief Information Officer at Share Our Strength (the organization behind No Kid Hungry), to unpack how fixing a decade of donor data unlocked new growth and collaboration across fundraising, finance, and IT.

Richard shares how a cross-department effort re-coded 10 years of donor data in just 90 days — transforming how Share Our Strength tracks restricted giving and opening new corporate funding opportunities. He explains why true data transformation isn’t just about clean systems, but about trust, teamwork, and a willingness to “get dirty” together to solve the right problems.

Richard discusses:

• Turning bad data into a growth opportunity
• Collaboration between IT, fundraising, and finance matters more than ever
• The business impact of clean, integrated donor data
• How Share Our Strength rebuilt 10 years of data in 90 days
• Leadership lessons from the Army that can strengthen nonprofit culture

In this episode of the Giving Growth Podcast, Greg Sobiech sits down with Lacey Stone, Chief Development Officer at USA for UNHCR, and Nathan Chappell, Chief AI Officer at Virtuous and co-founder of Fundraising.AI, to explore how non-profits can move beyond segmentation and embrace an AI-first approach to donor engagement.

Lacey shares how USA for UNHCR responded to the Ukraine crisis by welcoming 100,000 new donors and rethinking donor journeys — treating even small-dollar donors with the same care as major givers. She explains how listening, trust, and authentic stewardship are at the heart of retention and long-term loyalty.

Nathan brings his expertise in AI for social good, unpacking how predictive modeling and personalization can help charities build deeper donor relationships. He emphasizes why listening at scale, starting small, and creating a culture of curiosity are essential for successful AI adoption.

Together, they explore:

• What it really means to go “beyond segmentation” in fundraising
• How USA for UNHCR transformed an influx of emergency donors into long-term supporters
• Why listening to donors is often more powerful than traditional segmentation
• How nonprofits can use AI to prioritize limited staff time and deepen relationships
• Why 70% of AI initiatives fail and the cultural shifts needed to prevent it
• The small, consistent steps nonprofits can take today to move toward true personalization

In this episode of the Giving Growth Podcast, Greg Sobiech sits down with Chris Pritcher, General Manager at Data Axle and former CEO of RKD Group, to explore why non-profits are struggling to keep pace with today’s donors — and what they can learn from the for-profit world.

Chris explains why declining donor numbers aren’t just about economics or generational change, but about charities being outcompeted by consumer brands that connect more deeply and make giving easier. Drawing on his leadership experience across agencies serving hundreds of nonprofits, he shares how organisations can cut through jargon, focus on human connection, and make smarter use of data without overcomplicating things.

Chris shares insights on:

• Why charities are being outcompeted by consumer brands that connect more deeply with people
• How to move from channel-first thinking to a truly human-centric approach
• The danger of overinvesting in technology instead of focusing on simple, practical improvements
• Leadership lessons on shifting from managing processes to unlocking team potential
• Why leaders should question “good” results as much as they question “bad” ones

Drawing on decades as both a fundraiser and technologist, Nathan discusses why the nonprofit sector is at a tipping point: donor participation is shrinking, transactional fundraising is breaking trust, and traditional methods are no longer enough. 

As a solution, Nathan explains how AI can be used responsibly and ethically to reignite generosity, build stronger donor relationships, and free up time for more human connection.

Nathan shares insights on:

• Why AI may be the only scalable solution to today’s generosity crisis.
• How leaders can build a culture of curiosity that makes AI adoption work.
• What it means for a nonprofit to become “AI First”.
• Balancing efficiency with authenticity when using AI.
• Using precision philanthropy to deliver true personalization for donors.
• How to avoid making giving more transactional and instead build deeper trust.

With decades of experience as a fundraiser, author, and educator, Lisa explains the key differences between charity and philanthropy, why entrepreneurs are often overlooked as major donors, and what nonprofits can do to address the cracks appearing in the giving pyramid. 

She also shares her views on professionalising the nonprofit sector, rethinking overhead and salaries, and embracing tools like AI to better connect with supporters in an age of message overload.

Lisa provides us insights on:

• The key difference between charity and philanthropy — and why it matters for nonprofits.
• Why entrepreneurs are one of the most overlooked donor groups.
• How to avoid missing “diamonds in the rough” in your donor base.
• The impact of GoFundMe and peer-to-peer giving on traditional charities.
• What professionalisation means for nonprofits, from salaries to overhead.
• How digital tools and AI can help charities cut through the noise and engage supporters