In this episode of Lessons in Failure, Will Hold, MBA, CRM, CISR (CEO & President) and Mitch Dunford (CMO) sit down with Jenni Lee Crocker, South Leader of Alliant Insurance Services, to explore how resilience, self-awareness, and authentic connection have shaped her leadership journey. Jenni Lee reflects on her path from Ernst & Young to Marsh, PCF/Truecordia, and Alliant, highlighting that her success has not been defined by titles or accolades, but by the difficult moments that forced her to grow.

Jenni Lee shares a defining professional setback—losing a major client—that challenged her confidence and exposed gaps in how she was listening and engaging. What initially felt like a personal failure became a turning point, pushing her to confront assumptions, lean into humility, and rethink how she builds trust with clients and teams. She describes how that experience reshaped her leadership style, shifting her focus toward deeper listening, stronger alignment, and a more intentional approach to relationships.

Throughout the conversation, Jenni Lee breaks down the myth of the polished, always-in-control executive. Instead, she presents a more grounded and human perspective—one rooted in her identity as a mother, wife, and friend before anything else. She speaks candidly about navigating self-doubt, balancing career ambitions with family life, and the everyday realities behind high-level leadership. From her ability to connect with anyone she meets to her reputation for building meaningful relationships, she demonstrates how authenticity can be one of the most powerful tools a leader can have.