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What does a winning culture really look like?
In this episode of CEOs Unscripted, host Jane Gentry sits down with Rich Scanlon, Chairman of Sendible and a former NFL linebacker turned successful SaaS CEO. Rich shares his extraordinary journey from the football field to the boardroom, revealing how lessons in discipline, accountability, and high-stakes decision-making shaped his leadership style.
Tune in as Rich opens up about:
- Transitioning from professional sports to business
- Why athletes and military vets make great hires
- The power of clarity, trust, and transparency in leadership
- His biggest hiring mistakes—and how to avoid them
- How to make bold decisions without perfect information
- Why every CEO needs a personal outlet (and yes, the gym counts)
This conversation is packed with practical wisdom, unexpected laughs, and a whole lot of honesty. Whether you’re a first-time founder or a seasoned executive, Rich’s story will challenge how you think about leadership, risk, and what it really means to build a winning culture.
Episode Guest
About Rich Scanlon, Chairman for Sendible LTD
In addition to serving as the Chairman for Sendible LTD, an Alpine Software Group portfolio company, Rich Scanlon sits on the Advisory boards for multiple ASG companies. Rich has been a three-time CEO across multiple verticals at ASG prior to his current role. His background in sports drives his passion for teamwork, coaching/mentoring others, and the importance of company culture.
Scanlon’s business career began as a Management Consultant at Boston Consulting Group. Rich received his MBA from the Wharton School at University of Pennsylvania after having played five years in the National Football League as a linebacker for the Kansas City Chiefs, Tennessee Titans, and New York Giants.
