Maybank, who was the shopping website's founding CEO, eventually transitioned to Gilt's chief marketing officer. By the time she was ready to move, she found her second job at Gilt much more interesting than her first.
"There're some people who love every single phase," Maybank explains. "I never had a goal to run a public company. I never had a goal to run a 5-to-10,000 person business. I want to be part of it, but it's not what I love."
Maybank does, however, enjoy coming up with new ideas and getting them off of the ground. She knew that if she spotted an internal position that allowed her to do that, then she'd transition, she said.
Upon founding a company, it's important to imagine what your day-to-day might look like when you're simply not happy being the company's chief executive anymore, Maybank says.
"Have that honest conversation now so that they know the markers when they get there," she advises. "That criteria pops up, they recognize it, and they start making the plans to backfill or bring on that type of individual that loves that next stage of growth."
For more on leading your company through its various stages, check out the video below.