Damon Lembi on Baseball Dreams, AI, and Leadership Mastery

What happens when a star athlete with a leadership mindset steps into the world of business—starting at the front desk and rising to CEO? Well, Damon Lembi knows firsthand. Drafted by both the Atlanta Braves and the Yankees, he had his sights set on a professional baseball career. But when that path took an unexpected turn, he found himself in a completely different arena: the corporate world.

Rather than leaning on family connections, Damon started as a receptionist at Learnit, the company his father co-founded. But with the same work ethic and drive that made him a leader on the field, he climbed the ranks—eventually stepping into the CEO role just as the dot-com bubble was about to burst. What followed was a crash course in resilience, reinvention, and redefining leadership for a new era.

For over 30 years, Damon has been at the helm of Learnit, evolving it from a tech training company into a powerhouse for professional development. His insights on leadership, storytelling, and the future of work are shaped by his own journey—from navigating the highs and lows of entrepreneurship to embracing AI as a critical tool for the modern leader.

Meet Damon Lembi on LinkedIn: https://www.linkedin.com/in/damonlembi/ 

On his website: https://www.thelearnitallleader.com/podcast 

Extra Stuff:

I’m exploring what it means to stay grounded in an accelerating world. You’re welcome to follow along. For more depth, I share my best ideas at gobeyondthescroll.com

AI is moving fast. That doesn’t mean you have to feel behind.Explore my AI Literacy Training for smart people who want clarity, not chaos. Details at: https://maryloukayser.com/ai-literacy-training/ 

Books: https://maryloukayser.com/books-by-marylou 

Get in Touch:

LinkedIn: https://www.linkedin.com/in/mlkayser/

Instagram: @maryloukayser

Email: https://maryloukayser.com/contact-mary-lou-kayser/