The Long Game: Stephanie Dewald on Leading and Losing with Grace
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The Long Game: Stephanie Dewald on Leading and Losing with Grace
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In this episode, I interview Stephanie Dewald, Executive Vice President and Zonal Distribution Leader for Major Accounts at Chubb, who brings over three decades of exceptional industry experience. Stephanie shares her unexpected journey into insurance after starting out as a computer science nerd, and how those early tech roots continue to fuel her adaptability and curiosity today. We also dive deep into her powerhouse background as a Division I tennis alumna and endurance athlete, exploring how the discipline, structure, and lessons learned from handling defeat gracefully have shaped her professional resilience.
Beyond her athletic and career milestones, Stephanie offers powerful insights into modern leadership, discussing how she fosters a safe, collaborative environment for her team by treating mistakes as solvable learning opportunities rather than reasons for fear. We also examine the evolution of female leadership since the 1990s, the importance of embracing authentic strengths, and what it truly takes to drive sustainable, top-down equity and inclusion in the insurance industry so that leadership genuinely reflects a diverse customer base.