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 partnersChapters📌 LinksListen 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 strongThis 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 - Intro01:01 - Enterprise value for charities08:44 - Short-term targets vs long-term thinking15:40 - Evergreen fundraising and emergency giving20:56 - Personalization at scale29:36 - Obstacles to digital fundraising in 202636:39 - Step-by-step use of AI for donor segmentation40:06 - OutroListen 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 opportunityCollaboration between IT, fundraising, and finance matters more than everThe business impact of clean, integrated donor dataHow Share Our Strength rebuilt 10 years of data in 90 daysLeadership 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 fundraisingHow USA for UNHCR transformed an influx of emergency donors into long-term supportersWhy listening to donors is often more powerful than traditional segmentationHow nonprofits can use AI to prioritize limited staff time and deepen relationshipsWhy 70% of AI initiatives fail and the cultural shifts needed to prevent itThe small, consistent steps nonprofits can take today to move toward true personalization

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

In this episode of the Giving Growth Podcast, Greg sits down with Roger Hiyama, Community Leader at Delve Deeper and former Executive Vice President of Solutions and Innovation at Wiland, to confront a challenge every nonprofit leader needs to pay attention to: the collapse of the traditional donor pyramid.

SummaryIn 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.Chapters00:00 The Importance of Data Hygiene in Nonprofits02:44 Kate Hollandsworth's Journey and the Role of Acquire05:44 Common Challenges in Donor Retention08:54 The Need for Tough Conversations in Nonprofit Management11:34 Understanding Data Hygiene and Its Impact14:51 Investment Planning and Its Challenges17:33 The Role of Finance in Nonprofit Growth20:42 Navigating the Giving Pyramid and Donor Demographics23:33 Strategies for Retaining Donors26:35 The Future of Nonprofit Fundraising29:32 Brutal Honesty in Nonprofit ManagementFollow 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

In this episode of Giving Growth, Greg Sobiech sits down with Chris Hoffman from Compassion International to discuss how nonprofits can think more like subscription businesses. Chris shares how the AARRR framework Acquisition, Activation, Retention, Referral, Revenue adapted from B2C SaaS, applies directly to donor lifecycle strategy. 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 insteadHow the AARRR framework translates to donor lifecycle strategyThe role of experiential marketing in donor acquisitionHow to shorten time-to-impact for new donorsThe power of donor letters in driving retentionExamples of leading KPIs that nonprofits can trackHow to operationalize moves management from mass to major giftsWhy AI and summarization tools are critical to better donor engagementGuest 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 leadershipDevelopment & fundraisingDonor engagementMarketing or product in charitable organizationsData and digital transformation in the social impact space

In this episode of Giving Growth, Greg Sobiech sits down with Crashonda Andrew, Senior Vice President of Global Philanthropy at United Way Worldwide, to unpack the evolving role of philanthropy in a post-COVID, equity-driven world.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 trendThe role of data in building smarter donor strategiesLessons from managing relationships across 1,100+ United Way chaptersHow to future-proof your fundraising effortsWhat corporate partners are really looking for todayWhether 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.

SummaryThe 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.TakeawaysUSA for UNHCR gained 100,000 new donors due to the Ukraine crisis.Initial focus on donor retention was not effective.Segmentation of donors is crucial for tailored engagement.Non-financial engagement can build stronger donor relationships.Chapters00:00 Transforming Donor Engagement03:13 Strategic Planning and Organizational Change05:56 Understanding Donor Retention Challenges08:55 Building a Stewardship Team12:05 The Importance of Process and Infrastructure15:08 Segmenting Donors for Better Engagement17:58 Non-Financial Engagement Strategies20:59 Building Trust in Leadership23:45 Accountability and Organizational Culture29:02 Iterative Strategic Planning31:02 Empowering Leadership and Cross-Departmental Collaboration34:41 Building Trust and Accountability in Teams40:59 The Importance of Donor Engagement and Retention49:48 Navigating Risks in Humanitarian Funding

In this candid conversation, Greg sits down with Julie Upham to unpack what most nonprofits get wrong about retention—both of donors and staff. Drawing on decades of frontline fundraising experience, Julie shares:Why investing in people is just as critical as investing in donor strategyThe concept of “passion points” and how it transforms leadership and donor developmentThe underrated power of weekly check-ins, stay interviews, and skip levelsHow to prevent burnout and build a team culture people return to—even years laterThe parallels between growing donors and growing high-performing teamsPractical tactics for donor retention in an era of shrinking giving basesThe “moving finish line” problem in nonprofit fundraisingWhat nonprofit leaders can learn from sports, feedback science, and parentingHow Conservation International builds a culture of people-first leadership at scaleInsights from the Bridge Conference and why professional development is retention fuelThis 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.

In this episode, Dorota Amin pulls back the curtain on how the World Food Program USA builds high-impact, long-term partnerships with global brands like Google, Palantir, UPS, MasterCard, and the John Deere Foundation.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 impactHow the WFP is using predictive models to pre-position food before disaster strikesThe 34:1 ROI of anticipatory actionWhat makes trust-based philanthropy workWhy nonprofits must behave like system builders, not just respondersHow to earn the right to innovate within tight financial guardrailsWhy corporate partnerships start with cultural alignmentThe myth of the "pitch" and the reality of co-creationWhy 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.

In this compelling episode, Greg Sobiech, CEO of Delve Deeper, sits down with Brian Colombo, Deputy Chief Development Officer at Amnesty International USA. They explore how Amnesty builds authentic, long-term relationships with donors by deeply understanding and reflecting their values. Brian shares insights into Amnesty's unique shared leadership model, the rise of retail accountability among younger generations, and how nonprofits can foster trust while navigating the pressures of financial sustainability.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.

In this powerful episode, I sit down with Ben Webb, International Justice Mission's leader in marketing and branding, to discuss the transformative potential of nonprofits. Ben shares his philosophy on creating empathetic connections between donors and beneficiaries, redefining the role of marketing as a growth engine in the nonprofit sector, and uniting fundraising and marketing under a shared mission.Key Topics Covered:The Empathy Bridge: How stories connect donors to the mission on a deeply emotional level.Reimagining Nonprofits as Movements: Why success depends on everyone involved, not just employees.Tensions in Nonprofit Organizations: Addressing the divide between fundraising and marketing and fostering alignment for greater impact.Framework for Impact: Ben's five-step framework: insight-driven, concept-led, powered by stories, scaled by technology, and monitored for effectiveness.Personalization in Storytelling: Connecting universal truths to individual donor segments for meaningful engagement.The Power of Relationships: How building relevance and value can forge lasting bonds with donors.Breaking Stereotypes: Moving beyond outdated tropes to tell authentic, resonant stories.Operationalizing Empathy: Turning creative concepts into actionable, data-driven campaigns.The Role of Urgency: Keeping the mission central and maintaining a sense of urgency in transformative work.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.

Today I spoke with Ben Greene, Chief Revenue Officer for Charity Water. 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.

Today I spoke with Jennifer Roberti, CMO at Save the Children.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.