#53: Why Vulnerability Is a Superpower in Leadership – with Elizabeth Glasbrenner

In this episode of The Freedom Experience, I sit down with Elizabeth Glasbrenner — CEO of Smiley Technologies, a family-owned business providing core banking software to community banks and financial institutions.

Elizabeth’s story is one of courage, clarity, and people-first leadership. After co-founding the business in 2002 with her brother Vance and father Walter, she stepped into the CEO role in 2016 — not just to scale the company, but to rebuild trust, reshape the culture, and guide the business through a period of rapid growth.

In this conversation, Elizabeth opens up about what it took to make that transition. From navigating imposter syndrome to balancing extreme personal challenges — including her husband’s Everest expedition and her daughter’s life-threatening health issues — she shares what it really looks like to lead with empathy and authenticity, even when the stakes are high.

🎥 Watch this conversation on YouTube. And SUBSCRIBE!

Key Themes:

🔹 The Leadership Shift
Why the leader who starts the business isn’t always the one to scale it — and how Elizabeth found her own leadership voice.

🔹 Building Trust from the Inside Out
How Elizabeth rebuilt trust in the organization after stepping into her brother’s shoes — and why listening was her first strategy.

🔹 Leading Through Personal Crisis
Balancing high-stakes leadership with an intense family situation — and the strength that came from showing up fully in both.

🔹 Quiet Strength
Why vulnerability, empathy, and consistency became her edge — and how that reshaped the culture at Smiley Technologies.

🔹 Freedom and Leadership
What freedom means when you're responsible for others — and how Elizabeth learned to lead in a way that aligned with her values.

Quotes from the Episode:

💬 "You don’t need to know all the answers. You need to ask the right questions."
💬 "Trust is everything. Without it, nothing moves."
💬 "I thought I had to prove myself. What I really needed to do was show up as myself."
💬 "Listening was the most powerful thing I did as a new CEO."
💬 "Freedom is finding calm in the chaos."

Links & Resources Mentioned:

🌍 Smiley Technologies: https://www.smileytechnologies.com
📲 Connect with Elizabeth: https://www.linkedin.com/in/elizabeth-glasbrenner/

📚 Books Mentioned
– The Speed of Trust by Stephen M.R. Covey
– Dare to Lead by Brené Brown
– Quiet by Susan Cain

Actionable Takeaways:

✅ Step Into the Role: You don’t need to be the same kind of leader as your predecessor — just the one your business needs next.
✅ Lead with Empathy: Listening is often more powerful than directing.
✅ Rebuild from Trust: Sustainable growth starts inside the team.
✅ Embrace Your Season: Life and business don’t happen in separate lanes — lead with full presence.
✅ Redefine Success: It's not about doing more — it's about doing what matters most.

🎧 If this episode made you think differently about leadership, growth, or freedom — subscribe, share, and leave a review.
For more conversations on purpose, people, and building businesses that last, visit www.jeanmoncrieff.com.