Jaime Diglio
Founder,
inFirst Consulting and the WIN Room Program​
"I spent 20 years in corporate sales and leadership... I’ve been in the deals, led the teams, and recruited the talent"
Our founder, Jaime Diglio, knows what it’s like to be an ambitious leader who feels stuck and burned out.​ Through education, perseverance and practice, she learned how to get unstuck. Then, she created a step-by-step method for how leaders and their teams can do the same.​ Her programs combine AI data-driven insights and proven behavioral science and psychological strategies to help leaders identify and build up their strongest players. (In other words, she takes the winning concepts you’ve seen in Moneyball and Ted Lasso and applies them to corporate leadership.) She’s taught thousands at top companies, including Gartner, Microsoft, and Slalom, to use these principles and lead teams to exceptional success.
A Word from Jaime
Early in my career, I had an insane definition of success that pushed me to win at all costs. I didn’t even realize I was chasing after the wrong things, using the wrong measurements of success. And I wasn’t alone in thinking it’s OK to work until you drop. ​At Microsoft, Gartner and Slalom, I repeatedly saw the same invisible barriers holding people and teams back. And I saw the gap in leadership training that missed the real issues behind lagging sales, low productivity and high turnover rates.​ So, I created the WIN Room Program to address the root problems.
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When we start with what we are already good at, we accomplish more while doing less. This means we need to learn about our strengths, values and what drives us. I want to share with you this playbook for tapping into these powerful issues and take the guesswork out of winning.
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-Jaime
Jaime at Glance
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TEDx Speaker: From WAR Room to WIN Room
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Harvard Business School Sales Coach
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10+ years back to back Top Achiever
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Built a $40MM business from scratch going from 2-200 customers
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Grew and managed a $500M revenue stream.
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Held BDR, AE, Director, Manager, BU Leader Sales Positions
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College Soccer Captain at Bryant University
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Master’s degree in I/O Psychology from Fairfield U.
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Sales and Women’s leadership advisor
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Specializes in self-leadership & social intelligence
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Has advised CXO leaders across 300+ organizations.
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Sees every conversation as a sales conversation, which means everyone is in sales.
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Leads immersive, practical training combining Moneyball and Ted Lasso principles.
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Speaks at corporate events, trade conferences, and women’s groups.
Certifications
Trusted by Leaders in these Organizations
