Ola Sage: Charting her course in business and Chairing

As a Chair and a member, my Vistage experience has been like having an open MRI. It reveals who you are and creates an opportunity for personal discovery and growth as a leader.

Editor’s Note: This profile is part of a series highlighting Vistage Chairs — executive coaches who help guide CEOs and leaders of small and midsize businesses to make better decisions for their companies, families and communities.

Starting something new, specifically launching a business, can be as intimidating as exciting. But not for Vistage Chair Ola Sage. She grew up in a family of entrepreneurs and found the idea of charting her own course appealing.

Before launching her first company, a government professional services business, in 1999, she made a concerted effort to gain experience in various business roles. She sought ways to expand her knowledge in operations, sales, support and other areas necessary for being a CEO.

“I’ve always been pretty intentional about making business decisions,” she says.

The power of a peer group

Eight years into the business, a friend invited her to lunch and introduced her to Vistage, suggesting she join.

“I didn’t even realize I needed a peer group,” she says. “My first year was an eye-opening adventure.”

Through speakers, group meetings and one-on-one meetings, she experienced the power of the Vistage community. She appreciated the support membership provided, but a business crisis in 2012 also solidified how critical her peer group was to navigating challenges.

“The group rallied around me. They were my Tiger team,” she says. “They were there when I needed them the most and supported me until I was able to recover. I don’t think I would have made it through without them.”

Just a few years later, she started receiving unsolicited offers to purchase her business. With a lot of due diligence and persistence, she navigated and negotiated the right deal.

“I don’t think I would have been prepared for the sale had I not been in Vistage,” she says. “Speaker after speaker prepared me for the exit. Some of these things take years and require certain certifications. The knowledge I gained through Vistage ensured I worked through the process efficiently.”

Pushing beyond the known

After a successful exit in 2018, a fellow CEO shared that they thought she would make an excellent Chair. Again, her eyes opened to new possibilities, making her wonder, “Why didn’t I think of that?” She didn’t know who to call, so she visited the Vistage website, sent an email and reconnected.

After attending Chair Academy in 2018, she launched her CE group the following year and formed a Key Group in 2021.

“After my exit, I was advised to be careful about making major decisions too soon,” she says. “That didn’t last long — nine months later, I was a Vistage Chair!”

She regularly talks with CEOs about retirement and the next phase of life and encourages them to take time to decompress, be intentional and do something that is out of the rhythm of their work.

“When a member is considering exiting their business, one of my favorite questions is, ‘What are you retiring to?’” she says. “For me, being a Vistage Chair is something I want to do in retirement.”

Sage continues to run two businesses alongside her Vistage practice — CyberRx, a cybersecurity company, and a newly launched business, Carrot Cake Factory, celebrating her passion for the dessert. Sage does more than guide group members on their leadership journey, she “takes her own medicine.” In 2023, she joined fellow Chair Clyde Northrop’s group in Rockville, Maryland.

“As a Chair and a member, my Vistage experience has been like having an open MRI. It reveals who you are and creates an opportunity for personal discovery and growth as a leader,” she says. “Vistage groups give you a safe space to discover and rediscover the gifts you have that you’ve been stifling. In my No Limits CEO group, we push beyond the known, beyond the limits, to support members in pursuing their goals without feeling constrained.”

Taking time to play as hard as she works is equally important. Sage and her husband take a big transatlantic cruise annually. Leaving behind land and cars for an extended time on the high seas provides pure relaxation. They also enjoy all kinds of travel, good food, theater and time with friends.

Being involved in business is part of her DNA, and she doesn’t see that changing. Should she ever decide to “retire,” her Chair practice will remain part of what she does.

“It’s not just something I do; it’s a part of who I am,” she says.

Explore more coaching journeys

If this coaching story interests you and you’d like to see more, learn more about Chairing and how it could lead to the next chapter of your life.

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