A Conversation with EY Entrepreneur of the Year, Stephen Bailey

Rita McGrath
6 min readAug 29, 2022

It isn’t just anyone who can run an organization that has an impact on tens of thousands of leaders in over 100 countries, but ExecOnLine co-founder Stephen Bailey is that person. Prompted by a sense that access to high-quality online education could unleash career breakthroughs for diverse talents, the fast-growing company is a leader in its category.

The online executive education revolution

It was about 10 years ago that I was invited to participate in a partnership between Columbia Executive Education and ExecOnline. Though the idea of online education wasn’t new, the people at ExecOnLine seemed to have cracked many of its traditional problems. These include lack of engagement, boring course design, the inability to do the rich networking that takes place in traditional executive education programs and lack of choice and flexibility in the selection of faculty. These are all reasons why the promise of MOOC’s have proven so disappointing.

Today, ExecOnline is a force to be reckoned with, a pioneer in the world of on-line executive education with funding from venture capitalists and other investors of nearly $90 million and revenues of close to $60 million. My Friday Fireside chat guest, Stephen Bailey, is the driving force behind the concept, and I’m proud to be partnering with them.

So who is this guy?

Stephen Bailey was born and raised in New Orleans, to Black professional parents who deeply understood the value of education. His mother was a psychiatrist and his dad a dentist. As he waggishly likes to say, “I’m good from the neck up.”

He attended Emory University where he was part of the debate team and graduated with a degree in history. Next stop was Yale Law School, where he graduated in 2004, which was followed by a couple of years working at a law firm. Along the way, he got involved with connecting the founder of a startup, Frontier Strategy Group, with an investor. That got the wheels turning about the possibilities of creative work in the startup…



Rita McGrath

Columbia Business School Professor. Thinkers50 top 10 & #1 in strategy. Bestselling author of The End of Competitive Advantage & Seeing Around Corners.