Sherry Winn in

Sherry Winn

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Chief Executive Officer at The Winning Leadership Company
📍 Fishtail, Montana, United States

Sherry Winn is the CEO of The Winning Leadership Company, where she translates her experience as a two-time Olympian and national championship-winning basketball coach into executive leadership coaching. People who have worked with her describe her as resilient, transformative, and inspiring. She holds a Masters degree in sports administration from Ohio University.

Originally a multi-sport athlete in college, Sherry played basketball and softball at the University of Charleston, where she was valedictorian. Her athletic career culminated in competing for the US Olympic handball team in 1984 and 1988. In her free time, she has pursued interests like rock climbing and biking.

Unique fact: Despite a successful career as an athlete and coach, she didnt find true fulfillment until she invested in her own self-development and changed her belief systems.

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Experience
36 Years
Current Role
Chief Executive Officer
Job Level
Leadership
Location
Fishtail, Montana, United States
Personality Overview

How Sherry shows up

Communication Style
Decision Approach
Work Preference

Behavioral traits and communication patterns that shape how this person evaluates opportunities, builds trust, and makes decisions in professional settings.

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Priorities

Topics Sherry cares about

Olympic-Level Leadership
Sherry built her company around translating principles from elite athletics into the corporate world to help leaders perform under pressure and avoid burnout.
Combating Burnout
A core theme in her recent social media posts and company mission is helping executives master recovery and stop glorifying exhaustion as a measure of worth.
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Career

Work history

8-2015
Chief Executive Officer
The Winning Leadership Company
2015
Executive Leadership Speaker | Olympic Mindset Coach | Igniting Leaders & Teams to Win
The Winning Leadership Company
2020 - 2025
Sherry Winn Podcast Guest
The Winning Leadership Company
2016 - 2025
Three Times Best Selling Author
The Winning Leadership Company
2013
Olympic-Level Keynote Speaking That Transforms Leaders and Teams
Inside the Mind of a Champion: What the Best Leaders Do Differently
In the press

Media appearances

Sherry Winn - The Winning Leadership Company - Apple Podcasts. Featured in Apple Podcasts
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Sherry Winn: Two-Time Olympian & Motivational Speaker. Featured in The Winning Leadership Company – About Page
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Education
1986 - 1988
Master's degree
Ohio University
1984 - 1988
B.A.
University of Charleston
1984 - 1986
Bachelor of Arts (B.A.)
University of Charleston
Social presence
in
Behavioral profile

DISC profile (public)

DISC behavioral profile

Dominance, influence, steadiness, and calculativeness scores with guidance on how this person prefers to communicate and decide.

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