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 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.

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.

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.

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.

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

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

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.

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

In this conversation, Kate Hollandsworth, SVP of Strategy at Acquire, discusses the critical importance of data hygiene in nonprofit organizations and how it directly impacts donor retention. She shares her journey into the nonprofit sector, the common challenges organizations face, and the necessity of tough conversations for growth. The discussion also highlights the role of investment planning and finance partnerships in achieving long-term success, as well as the need for nonprofits to adapt to changing donor demographics and societal conditions. Ultimately, the conversation emphasizes the importance of transparency, data-driven decision-making, and a focus on retaining donors as key strategies for nonprofit growth.

Chapters

00:00 The Importance of Data Hygiene in Nonprofits

02:44 Kate Hollandsworth's Journey and the Role of Acquire

05:44 Common Challenges in Donor Retention

08:54 The Need for Tough Conversations in Nonprofit Management

11:34 Understanding Data Hygiene and Its Impact

14:51 Investment Planning and Its Challenges

17:33 The Role of Finance in Nonprofit Growth

20:42 Navigating the Giving Pyramid and Donor Demographics

23:33 Strategies for Retaining Donors

26:35 The Future of Nonprofit Fundraising

29:32 Brutal Honesty in Nonprofit Management

Follow Kate here:

Main site: www.akwiregroup.com

AKwire on LinkedIn = https://www.linkedin.com/company/akwiregroup/

Linkedin Personal Profile = http://linkedin.com/in/kate-phillips-hollandsworth-0174ba7b

Using real world examples from Compassion’s experiential marketing programs, Chris explains how deeply understanding donor needs and journey mapping can unlock new growth. From improving time to first-touch metrics to leveraging peer referrals and AI-driven donor summaries, this episode is a masterclass in growth thinking for nonprofits.

What You'll Learn:

• Why revenue is a lagging indicator and what to focus on instead
• How the AARRR framework translates to donor lifecycle strategy
• The role of experiential marketing in donor acquisition
• How to shorten time-to-impact for new donors
• The power of donor letters in driving retention
• Examples of leading KPIs that nonprofits can track
• How to operationalize moves management from mass to major gifts
• Why AI and summarization tools are critical to better donor engagement

Guest Bio: Chris Hoffman is Staff Product and Product Marketing Manager at Compassion International. With a background in B2C growth marketing and product development, Chris brings a unique perspective to the nonprofit sector, helping Compassion grow its recurring revenue through donor centric, data-driven strategies.

Listen if you work in:

• Nonprofit leadership
• Development & fundraising
• Donor engagement
• Marketing or product in charitable organizations
• Data and digital transformation in the social impact space

Crashonda shares what it takes to build sustainable donor relationships, how large institutions are reimagining global impact, and why equity must be a strategic driver—not just a buzzword.

They discuss:

• Why trust-based philanthropy is more than a trend
• The role of data in building smarter donor strategies
• Lessons from managing relationships across 1,100+ United Way chapters
• How to future-proof your fundraising efforts
• What corporate partners are really looking for today

Whether you're a nonprofit leader, institutional donor, or B2B brand in the impact space, this episode will leave you thinking differently about growth, partnership, and purpose.

The conversation explores the transformative journey of USA for UNHCR in adapting their donor engagement strategies following a significant influx of new donors due to the Ukraine crisis. The discussion highlights the importance of understanding donor retention challenges, building a stewardship team, and focusing on non-financial engagement to foster long-term relationships.

Additionally, the conversation delves into the significance of strategic planning, organizational culture, and accountability in achieving ambitious goals. In this conversation, the speakers discuss the iterative nature of strategic planning within organizations, emphasizing the importance of empowering leadership and fostering cross-departmental collaboration.

They highlight the need for trust-building within teams to ensure accountability and effective implementation of goals. The conversation also delves into the significance of donor engagement and retention strategies, particularly in the context of increasing humanitarian needs and decreasing public sector funding. Finally, they address the risks associated with funding in the humanitarian sector and the potential for breakthroughs amidst challenges.

Takeaways

1. USA for UNHCR gained 100,000 new donors due to the Ukraine crisis.
2. Initial focus on donor retention was not effective.
3. Segmentation of donors is crucial for tailored engagement.
4. Non-financial engagement can build stronger donor relationships.

Chapters

00:00 Transforming Donor Engagement

03:13 Strategic Planning and Organizational Change

05:56 Understanding Donor Retention Challenges

08:55 Building a Stewardship Team

12:05 The Importance of Process and Infrastructure

15:08 Segmenting Donors for Better Engagement

17:58 Non-Financial Engagement Strategies

20:59 Building Trust in Leadership

23:45 Accountability and Organizational Culture

29:02 Iterative Strategic Planning

31:02 Empowering Leadership and Cross-Departmental Collaboration

34:41 Building Trust and Accountability in Teams

40:59 The Importance of Donor Engagement and Retention

49:48 Navigating Risks in Humanitarian Funding

• Why investing in people is just as critical as investing in donor strategy
• The concept of “passion points” and how it transforms leadership and donor development
• The underrated power of weekly check-ins, stay interviews, and skip levels
• How to prevent burnout and build a team culture people return to—even years later
• The parallels between growing donors and growing high-performing teams
• Practical tactics for donor retention in an era of shrinking giving bases
• The “moving finish line” problem in nonprofit fundraising
• What nonprofit leaders can learn from sports, feedback science, and parenting
• How Conservation International builds a culture of people-first leadership at scale
• Insights from the Bridge Conference and why professional development is retention fuel

This episode is a masterclass in sustainable impact—not just through strategy, but through people.

🔗 Learn more about Conservation International

📩 For more interviews like this, subscribe to The Giving Growth Podcast.

Together with Greg, she explores how social impact organizations can be more than aid providers — they can be system builders, innovation incubators, and trusted strategic partners to the private sector.

From Google's weather forecasting in East Africa to John Deere’s trust-based innovation funding, this episode is packed with insights on how to create real, measurable change by aligning shared values, leveraging expertise, and building for the long term.

Key Topics Covered:

• Why partnerships—not donations—drive sustainable impact
• How the WFP is using predictive models to pre-position food before disaster strikes
• The 34:1 ROI of anticipatory action
• What makes trust-based philanthropy work
• Why nonprofits must behave like system builders, not just responders
• How to earn the right to innovate within tight financial guardrails
• Why corporate partnerships start with cultural alignment
• The myth of the "pitch" and the reality of co-creation

Why Listen:

If you lead a nonprofit, manage corporate partnerships, or work in CSR/philanthropy, this conversation is your playbook for creating enduring impact through private sector collaboration.

Key Highlights:

• How Amnesty’s shared leadership model empowers members and strengthens the mission.
• The concept of “retail accountability” and its growing importance for younger donors.
• Why reflecting donor values is essential for long-term engagement and trust.
• The challenge of balancing authentic messaging with financial constraints.
• Strategies for fostering community, interdependence, and stronger donor relationships.

Why Listen?

If you're leading a nonprofit or navigating donor engagement, this episode offers fresh insights on building trust, fostering authenticity, and strengthening community connections to drive sustained impact.

Key Topics Covered:

1. The Empathy Bridge: How stories connect donors to the mission on a deeply emotional level.
2. Reimagining Nonprofits as Movements: Why success depends on everyone involved, not just employees.
3. Tensions in Nonprofit Organizations: Addressing the divide between fundraising and marketing and fostering alignment for greater impact.
4. Framework for Impact: Ben's five-step framework: insight-driven, concept-led, powered by stories, scaled by technology, and monitored for effectiveness.
5. Personalization in Storytelling: Connecting universal truths to individual donor segments for meaningful engagement.
6. The Power of Relationships: How building relevance and value can forge lasting bonds with donors.
7. Breaking Stereotypes: Moving beyond outdated tropes to tell authentic, resonant stories.
8. Operationalizing Empathy: Turning creative concepts into actionable, data-driven campaigns.
9. The Role of Urgency: Keeping the mission central and maintaining a sense of urgency in transformative work.
10. Transformative Value: The mutual growth and purpose that come from engaging in mission-driven work.

Takeaways:

• The nonprofit sector must pivot toward a people-centered, movement-driven model to stay relevant to future generations.
• Storytelling isn't just a tool for marketing; it’s the bridge to purpose and action.
• Aligning fundraising and marketing efforts is essential for creating sustainable growth and deeper engagement.

Their mission is to bring clean and safe drinking water to every person on the planet.

Whether you are in marketing - for a commercial minded - or mission driven organization - this conversation will be relevant.

Ben shared with me his marketing philosophy, which he calls “Look in, Look up, Look out”.

‘Looking in’ is about marketers not just owning - but dominating their most valuable audiences, their ‘superfans or superdonors’, with one simple message.

So much Marketing value - can be unlocked by looking IN first, and in this episode you’ll find out how.

They are on a mission to improve the lives of children through better education, health care, and economic opportunities, as well as providing emergency aid in natural disasters, war, and other conflicts.

This episode is all about the need for marketers to have a long-term vision and the importance of taking calculated risks.

Jennifer shared with me her insights on balancing the emotional and logical aspects of marketing, she emphasised the importance of both brand engagement and practical metrics. We also discussed the similarities between finance and marketing strategies when building for the long term and delivering outstanding results.

Jennifer's philosophy revolves around building long-term relationships with diverse audience segments and continuously innovating to stay ahead of the curve. She also highlighted the personal challenges of balancing work and home life in today's fast-paced, remote work environment.

Navigating the complex landscape of marketing leadership is difficult. It requires you to drive meaningful engagement for your organization for the long and short term.

From Delve Deeper, this is Narrow Lanes.

Partners in Health is an International non-profit that provides healthcare in the poorest areas of developing countries.

Francesco believes the only way for marketers to stay in leadership roles for 5 years plus, and have the runway to create lasting transformative value is to be polyvalent. This means that marketers can be useful in more than one way. This person must have both broad and deep expertise and experience.

He recommends that marketers get outside of their comfort zone, and take on many new roles, more often - to build up proficiency within areas where they currently lack experience.

For instance, Francesco believes that marketers need to be proficient in the application of 1st party data - to drive revenue growth. This is crucial because when 3rd party cookies go away, brands will need to embrace their own 1st party data if they want to grow.