Meet Jaime

Jaime Diglio is the Founder and CEO of The WIN Room™, a practice-based performance system that helps leaders and teams move from self-doubt to consistent results. She is the author of Moneyball Leadership, a TEDx speaker, and a Harvard Business School sales coach.

Before founding The WIN Room™, Jaime spent 15+ years as a top 1% performer at Gartner and Microsoft. A stress response that landed her in the ER became her wake-up call: she walked out of the WAR Room and built the WIN Room instead.

Today, Jaime works with leaders and teams across more than 300 organizations in a variety of industries, helping them strengthen executive presence, define their winning formula, and make money in every conversation. Her method is grounded in neuroscience and sports psychology, with 98.4% of professionals who work with her hitting their goals.

Jaime Diglio Founder and CEO of The WIN Room™

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Founder & CEO, The WIN Room™

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Moneyball Leadership Jaime Diglio Founder and CEO of The WIN Room™

WIN THE GAME BY
CHANGING THE WAY
YOU LEAD

Forget generic leadership advice. Jaime gives you the exact mindset, method, and moves behind her clients' breakthrough results, so you know who you are, lead like you mean it, and Measure What Matters.

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Praise for Moneyball Leadership

"If your sense of self is wrapped up in your work, what happens when you start to lose sight of who you are? This book helps you confront that question head-on."