
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.

Certifications & Affiliations














JAIME BY THE NUMBERS
10+
$40M
300+
$500M
10K
Years Back to Back Top Achiever
Size of Business Built from 2 clients to 200
Number of CXO Leaders Advised
Revenue Stream Grown and Managed
Number of hours spent driving her kids to sports practices
Change Your Room. Change Your Life.
Jaime breaks down the WIN Room on the TEDx stage

TRUSTED BY Leaders At






























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