Frontdesk names new CEO as Weatherly becomes board director

See Correction/Clarification at end of article

At the end of this month, Kyle Weatherly will wrap up his day-to-day work as CEO of Frontdesk, the short-term rental startup he co-founded in 2017.

Weatherly will remain involved with the company as its board director and his co-founder, Jesse DePinto, will become the new CEO, the company announced Sept. 1.

During his final month of full-time work with the company, Weatherly is focused on ensuring a seamless handoff to DePinto, who previously served as Frontdesk's chief product officer.

After that, only two things are certain for Weatherly: He plans to travel with his wife and then get back to work in some capacity, he said. In this way, things are coming full circle.

"This will probably end the same way it began," Weatherly said. "When I left my last company in January 2016, I had no idea what I was going to do next. We knew we wouldn’t regret taking a year off to travel."

Weatherly is referring to when he stepped down as president of medical compression garments maker Solaris Inc. after its 2014 sale to a European medical device company.

At the time, Weatherly wasn't sure whether he wanted to retire, return to his early-career roots in the nonprofit sector, purchase an existing business or pursue entrepreneurship, he said. As he and his wife traveled around the world, they enjoyed staying in Airbnbs but craved some of the comforts of a hotel experience, which is where the idea for Frontdesk was born.

This time around, Weatherly is certain an early retirement isn't on the table. He has no direct plans for what he'll do next but said he experienced a "malaise" after a few months without working in 2016 that he doesn't want to repeat.

Weatherly, one of the Milwaukee Business Journal's 40 Under 40 honorees in 2014, said his upcoming travel plans include Costa Rica, Copenhagen and Cancun, among other places.

As for Frontdesk, DePinto hinted in a recent LinkedIn post that the company is preparing another big announcement.

"We're entering a new phase of growth," DePinto told Wisconsin Inno. "We're at an inflection point in the business where we have executed phase one of our strategy and we're embarking on phase two."