From Corporate Retail to Youth Non-Profit CEO: Making Fundraising Fun | Lillian Samuel
In this inspiring episode of the HumanizeHer Podcast, we dive deep into the career and life journey of Lillian Samuel, the CEO of Big Brothers Big Sisters of the Bay Area. Breaking down the corporate armor, Lillian shares her story of transitioning from a high-flying executive retail career - managing global sourcing and buying for brands like Bloomingdale’s, Gap, and Cost Plus - to becoming a transformative nonprofit leader who has raised over $100 million for youth and healthcare initiatives.
Lillian’s parents raised her on one rule: pay it forward. So she volunteered, mentored, and threw parties for causes - until a mentor asked, "Have you ever thought about this as a career?" As a mom of three, she went back to school for a master's in nonprofit administration, then raised money for medical research at UCSF and led fundraising for Girl Scouts of Northern California. Today she's President and CEO of Big Brothers Big Sisters of the Bay Area, matching young people with mentors across nine counties. In five years, she's doubled the budget, cut the waitlist in half, and led the agency to its first-ever national Quality Award. Over her career, she's raised more than 100 million dollars - and she'll tell you fundraising isn't hard. It's about relationships and having fun!
Lillian discusses the life-changing impact of mentorship, sharing how pairing caring adult role models with young people creates long-term positive outcomes, from boosting school performance to keeping youth out of the juvenile justice system. She redefines fundraising not as a daunting chore, but as a joyful practice of connecting passionate donors to meaningful causes and building lasting relationships. Throughout the conversation, Lillian opens up about leading as a neurodiverse executive, overcoming self-doubt through validating feedback, navigating quiet fundraising campaigns, and the vital role mentorship has played across every stage of her own life.
Key Highlights:
The Power & Efficacy of Mentorship: How Big Brothers Big Sisters uses technological matching and deep community partnerships to connect youth with caring adults, resulting in measurable long-term successes like increased college attendance and boosted self-confidence.
Corporate to Nonprofit Pivot: Lillian’s transition from international corporate retail travel to a mission-driven career that allowed her to stay closer to family while scaling community impact.
Reframing Fundraising as Connection: Why fundraising is really about storytelling, listening, and inviting donors to invest in a shared vision rather than hard pitching.
Leading with Neurodiversity & Authenticity: Lillian shares her experience with neurodiversity, the importance of building teams that complement your strengths, and learning to accept positive board feedback without self-doubt.
Pioneering Planned Giving & Financial Literacy: The lasting legacy of estate planning gifts for charities, alongside new initiatives teaching financial literacy and stock market skills to both mentors and youth.
"If you like people and enjoy talking to people, and if you're passionate about something, then fundraising should come easy. Because it's really about connecting people to something that they may care about. They may not know that they care about it until you share the story." - Lillian Samuel
Special Shoutouts in this Episode:
Lillian's Parents ❣️
Listen in and join the conversation with host, Erica Lockheimer and co-host, Elizabeth Wendorf-Bloesser.
🎧 Sound Credits: Elad Marish with Swell Sound
Timestamps:
00:00 – Welcome & Introduction
03:15 – What is Big Brothers Big Sisters?: Mentorship, community impact, and how matching works
08:20 – Program Demographics & Preventative Impact: Serving youth with incarcerated parents, keeping kids on track
13:45 – From Corporate Retail to Philanthropy: Transitioning from international buyer to nonprofit executive
18:10 – Earning a Master's in Nonprofit Administration & Building a Career in Fundraising
22:30 – Stepping into the CEO Role at Big Brothers Big Sisters: Doubling the budget and expanding reach
25:00 – The Art of Fundraising: Why asking for money is about relationships and listening
29:15 – Planned Giving & Estate Planning: Leaving a legacy that sustains charitable missions
31:40 – Career Growth, Neurodiversity, and Accepting Positive Feedback
34:20 – Current Initiatives: The 1000-kid goal, quiet phase campaigns, and real match success stories
37:50 – Financial Literacy for Youth and Mentors
39:15 – Paying It Forward: Shoutouts to mentors, parents, and advising the next generation
