When the founder of a multimillion-dollar company met her now-CEO, she disliked him immediately — but a 20-minute conversation changed her mind

Hollis Johnson/Business InsiderDrybar founder Alli Webb.
  • Drybar is a hair salon for blow-outs founded by Alli Webb alongside her husband and brother in 2008. To date, the store has more than 100 locations around the United States.
  • Her brother, Michael, was serving as the company’s CEO when they started receiving pressure from investors to bring in a more experienced CEO.
  • They brought in multiple candidates, and at first, Webb thought now-CEO John Heffner was too corporate.
  • But after chatting for 20 minutes, she knew he was the right person for the job.

Alli Webb founded Drybar, a hair salon for blow-outs that today has more than 100 locations around the United States, with her brother and her husband in 2008.

Her brother, Michael, was serving as the company’s CEO when they started receiving pressure from investors to bring in a more experienced CEO, Webb said on an episode of Business Insider’s podcast “This Is Success.”

Webb was sceptical. She explained: “I also felt like, Michael’s doing such a great job, we have this great partnership, and I felt like, if we brought somebody else in from the outside, it was going to change the culture, and I was very against it.”

But her brother was open to bringing in an outsider. “I think he recognised the fact that he’d never been a CEO before, he’d taken the company pretty far, but it may be time for somebody who actually had experience with this level of management that it would require,” she said.

The Drybar team met with several potential CEOs, many of whom Webb thought were qualified, but came with huge salaries and ideas for major company culture shifts. When Webb first met John Heffner, the current CEO of Drybar, she thought, “‘No. No way.’ We need someone cool. This guy isn’t cool.”

Webb said he was 6’2″ and as corporate-looking as they come.

“Shame on me,” she said. “I judged him so much by the way he looked, but, after we spoke to him for 20 minutes, I was like, ‘Oh my God, I love this guy.'”

Heffner came from OPI with a long career in the beauty industry. Webb said his history working with founder-led organisations and understanding that he couldn’t come in and overhaul the company is what sold her.

“I remember him making this analogy of me, Michael, and him being a three-legged stool. Without the three of us, everything falls apart. I was like, ‘That’s a good one,'” Webb said. “Because I felt like that was what we needed, was somebody who was going to come in and partner with us, versus someone who’s going to come in, like this ivory tower, and change everything.”

Since hiring Heffner, Webb said he hasn’t changed the culture or core of Drybar, but provided the management they needed.

“If I’m being totally honest, there’s times that I don’t agree with all the decisions that are made, and that is a really hard pill to swallow,” Webb said. “But it’s like, we have to keep going, and we have to learn from our mistakes, and we have to look back and say, ‘You know what, we should have done this differently, but here we are.’ I think that’s all part of the learning and growing process.”


Listen to the full episode and subscribe to “This Is Success” on Apple Podcasts or Art19.

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