Street Culture: Sitter.me CEO on Owning Mistakes and Terrible-but-Fun Team Building

Childcare app Sitter.me is three years old and recently moved to a new headquarters in Denver. Co-founder and CEO Kristen Stiles says the company’s cultural direction is still shaped by its leadership, but it’s also unconventional.

“It’s definitely a kind of laid-back environment,” Stiles told Street Fight in an interview. “We adopted some things from Techstars around celebrating failures. It’s really hard for some people to admit when they’ve failed or made a mistake, but in our culture we don’t just admit it, we announce it to everyone and then laugh about it.”

Sitter.me has grown in the last year from three and a half employees to seven full-timers—though the company is still very much in the beginning stages of growth. After completing the in-house Techstars accelerator program in Boulder, Colo., the team moved to a Spaces co-working location in Denver.

A recently celebrated failure is especially telling of the culture at Sitter.me, Stiles says.

“It was actually something I did,” she says. “I completely screwed up where I gave a major client the wrong price. We have a new B2B model helping nanny services to use technology, but we’re in the early stages. I had quoted a price to this major customer, and then changed the price and it was much higher.”

After apologizing profusely to the client, Stiles took the opportunity to lead by example, and called out her own blunder to the entire team.

“How we view mistakes is you admit it, you learn very quickly, and then turn it around,” she says. “We immediately put a structure in place for the sales process where we have all the client information in one place, including the quoted price.”

“The thing that always comes to mind is Peyton Manning,” she says. “If he’s having a fabulous quarter and then all of a sudden he throws an interception, he can’t sit there and dwell on it, otherwise he’s just going to throw another one. He has to address it and move on and throw a great pass the next time. Admit it, fix it, move on.”

The company’s hiring process is still evolving, partially because the company itself is still quite small. So far, Sitter.me has hired only one employee through the traditional system of resume submission and review—for marketing coordinator Elena Shaw, who started as an intern. Two other recent hires connected via professional networks: Sarah Molk, who unexpectedly connected via one of Sitter.me’s customers, and Stephanie Burdick, a former employee of Stiles.

Sitter.me’s office is in tight quarters, and everyone knows that a new person will have to fit in from the beginning. Stiles says the interview process entails the candidate coming to the office and spending a couple of hours getting to know all the employees and what they’re working on. This practice makes for a better atmosphere all around—a goal the team also works toward through the go-to activity of community volunteering. The staff has participated in four volunteer events so far and plans to do one every quarter.

“The first one was really the best,” Stiles says. “Matt [Stueve, co-founder and CTO] is a big outdoor enthusiast and hiker, so he wanted to plan a community service thing where we go and help fix trails with Boulder County Parks and Open Space. We thought we were going to go out, do some trail building—‘Oh, sounds fun.’”

The rest of the team then found out that they were going to be loading a wood chipper with chopped-down branches from an invasive species of trees near Boulder Creek.

“As a volunteer, you don’t really know the exact kind of thing you’re going to be doing. It was July. It was 100 degrees out. I’ve never been so hot,” Stiles says, starting to tear up with laughter at her story. “We had to wear jeans and long-sleeve shirts, and these huge helmets that were scorching hot; you couldn’t hear anything because you had these big ear things on, dripping sweat.

“We were dumping buckets of creek water on our heads to cool off. And we had talked another Techstars company into doing this with us—they left. They were like, ‘We’re never doing another community service project with you ever again.’ But one thing about our culture, if we say we’re going to do something, we do something. We promised we would do this, we had committed, and we stuck it out. But we thought we were going to die. It was so much fun and so terrible at the same time.”

In this case, fun and terrible were a great combination for team building. Stiles also touches on one point about culture that she learned from a previous position: It’s a success for the company if an employee grows so much that they need to move on.

“One of the things that I think is so important, this was an HP Way value that I learned, was if somebody moves on because they develop skills at your company and they want to take those skills further, and we just can’t offer that kind of capacity of work, then it’s a celebration of success of the company,” Stiles says.

“That’s what happened with Emily [Stockton, former Sitter.me employee]. She learned a ton; she was a speech language major. We had her learn about social media and other marketing stuff, and she went on and became a full time social media manager. We just don’t have that kind of need at our company yet. But I just talked to Emily yesterday.”

April Nowicki is a staff writer at Street Fight.