Real Talk. Real Growth. Real Results in the Mid-Market
Jane Gentry consulted in enterprise for 20 years. And, after being a CEO in a mid-sized company, she realized why they say it is loneliest at the top. Mid-market CEOs learn their craft through trial and error or by reaching outside their organization for help. She launched CEOs Unscripted as a bi-weekly podcast by mid-market CEOs for mid-market CEOs. Our purpose is to provide insight into the unscripted, unfiltered journeys of CEOs and Founders as they talk about their wins, losses, lessons and playbooks for growing and scaling their organizations. There is no better forum than learning from your peers.
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Real Talk. Real Growth. Real Results in the Mid-Market
Jane Gentry consulted in enterprise for 20 years. And, after being a CEO in a mid-sized company, she realized why they say it is loneliest at the top. Mid-market CEOs learn their craft through trial and error or by reaching outside their organization for help. She launched CEOs Unscripted as a bi-weekly podcast by mid-market CEOs for mid-market CEOs. Our purpose is to provide insight into the unscripted, unfiltered journeys of CEOs and Founders as they talk about their wins, losses, lessons and playbooks for growing and scaling their organizations. There is no better forum than learning from your peers.
From the NFL to the C-Suite: Rich Scanlon's Journey of Calculated Risk-Taking
CEOs Unscripted
49 minutes
3 months ago
From the NFL to the C-Suite: Rich Scanlon's Journey of Calculated Risk-Taking
In this episode of CEOs Unscripted, host Jane 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.
Timestamps:
Introduction and Welcome - 0:00
Rich Scanlon's Background and Journey - 2:15
Transition from NFL to Business - 5:30
Decision-Making and Risk-Taking - 12:45
Accountability and Team Dynamics - 18:20
Career Development and Flexibility - 25:10
Maintaining Engagement and Trust - 32:00
Rapid Fire Questions and Closing Thoughts - 40:15
Conclusion and Call to Action - 45:00
CEOs Unscripted
Real Talk. Real Growth. Real Results in the Mid-Market
Jane Gentry consulted in enterprise for 20 years. And, after being a CEO in a mid-sized company, she realized why they say it is loneliest at the top. Mid-market CEOs learn their craft through trial and error or by reaching outside their organization for help. She launched CEOs Unscripted as a bi-weekly podcast by mid-market CEOs for mid-market CEOs. Our purpose is to provide insight into the unscripted, unfiltered journeys of CEOs and Founders as they talk about their wins, losses, lessons and playbooks for growing and scaling their organizations. There is no better forum than learning from your peers.
