Former NFL, NBA, and Super Bowl Chief Sales Officer; Founder & CEO of Win Monday™

Former NFL, NBA, and Super Bowl Chief Sales Officer; Founder & CEO of Win Monday™
Paul Epstein is a former NFL, NBA, and Super Bowl chief sales officer, now two-time bestselling author and award-winning speaker named one of SUCCESS magazine’s top thought leaders that get results—alongside Tony Robbins, Brené Brown, Gary Vaynerchuk, and Mel Robbins—and his work has been featured on ESPN, NBC, Fox Business, and in USA Today.
During 15 years as a leader in the professional sports industry, Paul led revenue and culture at the highest levels. He helped transform numerous NBA teams from the bottom of the league in revenue to the top two, shattered every premium sales revenue metric in Super Bowl history while in the NFL’s league office, opened a billion-dollar stadium, and founded the San Francisco 49ers Talent Academy and Leadership University, earning the nickname “The Why Coach” for his ability to align people, purpose, and performance.
Today, Paul is the Founder & CEO of WIN MONDAY™, a leading habitbuilding company that drives momentum, growth, and repeatable success for championship cultures across the globe.
Offstage, he is a proud father of PJ and Lucca, married his best friend on the field of Levi’s Stadium, and has a slight obsession with bacon—just don’t make it too crispy.
Monday isn’t just another day. It’s the most reliable performance habit of your entire week. Every seven days your team gets the same reset. The only question is: does that reset spark winning actions and momentum or default to comfort and stagnation?”
Win Monday vs. Waste Monday. We always get to decide.
According to research inside Win Monday’s Habit Lab, this performance gap is the reality for most organizations—as 86% of employees consider Monday their worst day of the week, yet 98% of people who accomplish something meaningful on Monday feel momentum their entire week.
What if Monday became your team’s competitive edge?
In this keynote, former NFL and NBA executive and bestselling author Paul Epstein reveals the weekly habit that separates champions from everyone else — flipping Mondays from missed opportunities into momentum drivers that lead to lasting growth and success.
When winning Monday becomes your organization’s “go-to” habit, you win everything that follows. Are you ready to Win Monday?
Leading with Confidence through Change and Adversity
In today’s business environment, competitive threats, unrelenting change, rising customer expectations, and economic uncertainty have us all playing defense.
The result? Confidence gaps are created that drive defensive mindsets and actions in organizations across the world.
But what if you had a playbook for playing offense — proactively pursuing and achieving meaningful goals and breakthrough performance — while everyone else is sheltering in place?
This is exactly what Paul delivers in this foundational keynote inspired by 15 years of leading sales teams in the NFL & NBA and his bestselling book, The Power of Playing Offense. Every audience member will walk away with a 5-pillar Playing Offense framework and WIN MONDAY™ playbook, curated for universal insights and actionable takeaways to implement in any industry or organization.
Culture can only scale when EVERY person in it takes full ownership, accountability, pride, and a commitment to daily excellence.
That’s the spirit of a championship culture (when done right) – and can be your ultimate competitive advantage.
This keynote is inspired by Paul’s 15 years as a culture-building practitioner in the NFL and NBA– including multiple national awards for his work as Founder of the San Francisco 49ers and Leadership University. Through extensive testing in his WIN MONDAY™ habit lab, he has identified what unites the world’s most remarkable cultures.
The biggest needle-moving insights are revealed in Scaling Championship Culture, centered around a foundational battle cry to WIN MONDAY™.
This is not your average ‘top down’ approach to culture – rather, the program introduces a framework that empowers every individual and team to take ownership of their local culture while ensuring they feel recognized for their talent and contributions.
As a result, every team member performs to their highest standard and delivers the championship results required to WIN.
How did Paul lead his teams to consistently sell out billion-dollar NFL stadiums with 70,000 fans in historically losing markets? Or transform an NBA team’s revenue performance from 28th to 2nd in the league – despite being labeled by ESPN as “the worst brand in sports”?
The answer lies in a powerful, scalable belief system that can be applied to any sales or service environment: Every seat has a story.
This shift from blanket ‘catch all’ campaigns to a dynamic customer-to-customer approach driven by customization, care, and championship service, led to sold-out stadiums and record-breaking revenue, that didn’t hinge on wins or losses.
In the sports industry, every seat and fan had a story. In your case, every client has a story. The question is: “Will you get to know it?”
Achieving customer success doesn’t depend on perfect market conditions – it depends on consistently making each customer feel valued and seen. This keynote is HOW to do it, one story at a time.
Even the most elite performers can rush to bad judgments, become paralyzed by indecision, or get worn down by decision fatigue.
In this keynote, Paul reveals the streamlined three-step process he used to turn around major sports franchises — from the locker room to the boardroom. Avoid decision traps, move forward with clarity and confidence, and make the best out of your MVDs: Most Valuable Decisions.
Discover the key to making fast and effective decisions for the questions that keep you up at night:
The secret? The Head-Heart-Hands equation: a simple and repeatable process that taps into the power of our three most basic human tools for making better decisions faster.
Contact CAA Speakers at (424) 288-2898 or speakers@caa.com to book Paul Epstein to speak at corporate or private events, keynote speeches, speaking engagements, workshops, fireside chats, motivational speaking, or virtual appearances.
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Yes, Paul Epstein speaks at virtual events with professional-grade equipment and interactive presentation style.
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Yes, Paul Epstein speaks at private corporate events, executive retreats, board meetings, and exclusive functions.
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Book Paul Epstein 3-6 months in advance for best availability, especially during peak speaking seasons. Early booking ensures better date selection and rate negotiations.
Recommended booking timeline:Peak seasons: September-November and March-May book fastest. Contact CAA Speakers early for priority consideration.
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