#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.