Jaime Diglio: From Corporate Burnout to Building The WIN Room

In this episode of Founders Future, with host Milan Kohut, Jaime Diglio, Founder and CEO of The WIN Room, shares how a personal health scare during her time as a sales leader at Gartner became the catalyst for building a performance coaching company rooted in mindset mastery. After experiencing a severe stress response that left her temporarily unable to feel her legs, Jaime realized that traditional leadership and sales training overlooked a critical piece: how individuals manage pressure internally. Drawing from her background in organizational psychology and enterprise leadership—including managing a $450M Microsoft business—she developed The WIN Room methodology to help professionals shift from what she calls the “War Room” mindset (self-doubt, comparison, reactive thinking) into the “WIN Room,” where clarity, intention, and performance align.Jaime works across both organizations and individuals, coaching leaders in transition, high-potential talent, and ambitious professionals who want to sharpen executive presence, communication, and confidence. Through group programs, individual coaching, and her growing community membership, The WIN League, she focuses on long-term behavioral change rather than quick-fix tactics. In a world obsessed with scripts and scalability, Jaime challenges companies to prioritize authenticity over uniformity—helping people build their own “winning formula” so they can perform under pressure without losing themselves in the process.