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Meet Jaime Diglio

Jaime Diglio is the Founder and CEO of The WIN Room™ and author of Moneyball Leadership. She spent 15+ years as a top 1% performer at Gartner and Microsoft before a stress response landed her in the ER and changed everything.

That moment was her wake-up call. She walked out of the WAR Room and built The WIN Room™: a practice-based method that shifts leaders and teams from self-doubt to self-leadership.

Today, Jaime is a TEDx speaker, Harvard Business School sales coach, and high-performance coach to leaders across more than 300 organizations. She works with professionals to strengthen their executive presence and define their winning formula so they can build trust, create value, and make money in every conversation.

Her method is grounded in neuroscience, sports psychology, and the New ROI: Return on Interactions™. 98.4% of professionals who work with her hit their goals.

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Certifications & Affiliations

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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 success.

This isn’t about checking boxes. It’s about knowing who you are, leading like you mean it, and measuring what actually 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."