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Meet Jaime

Jaime Diglio is the founder of the WIN Room and author of Moneyball Leadership. She has a background in organizational psychology with proven methods in sports psychology, social intelligence, and competitive knowledge.

After 20 years leading top-performing sales teams at Microsoft, Gartner, and Slalom, she hit a wall and couldn’t find the support she needed to push forward.

That moment became her wake-up call. She walked out of the WAR Room and built the WIN Room: a space where purpose leads, and performance follows.

Today, she helps leaders trade hustle for purpose and lead from within. Her WIN Room programs have transformed Fortune 500 companies and high achievers around the world.

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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."