In this powerful episode of It’s Not You, But Sometimes It Is, we sit down with Jesse Skelzy, CEO of Really, for a raw and refreshingly honest conversation about leadership, motherhood, and the messy middle of rapid career growth.
From climbing the ladder fast to navigating executive roles while raising two young kids, Jesse gets real about the challenges she faced—and the mistakes she made along the way. We talk about everything from imposter syndrome and cultural dysfunctions to what it really means to lead with both high standards and heart.

Jesse opens up about:
• Juggling life as a CEO and mom of two
• Learning to lead through vulnerability
• The pressure to have it all together—and why that’s a myth
• Building trust on leadership teams
• What she learned from both great mentors and bad bosses
• How to support (and retain) high-performing teams
• The mindset shifts that helped her stop being her own worst enemy

Whether you’re an executive, a new manager, or someone striving to balance ambition with authenticity, Jesse’s insights will inspire and challenge you.

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