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