Street Culture: Sitter.me Puts Company Culture of Trust and Respect First

Barely a month after kicking off in the TechStars startup accelerator program in Boulder, Colorado, Sitter.me co-founder and CEO Kristen Stiles is adamant that her company’s culture will not change – not now, with three and a half employees, and not years from now, with potentially hundreds.

“When I sat down, before [co-founder] Matt came on board, to first write out a business plan because I’m a traditional business person, the first section I completed was about the cultures and the values,” Stiles says. “It won’t ever change. It just won’t. The culture starts at the top and stays with the top and there is nothing more important than leading by example in that respect.”

Sitter.me, a two-year-old app company – Stiles says she considers it a business, not a startup – connects parents with local babysitters, trusted people who the neighbors would vouch for.

The three and a half employees are Stiles, co-founder and CTO Matt Stueve, developer Lonnie Moy, and part time “resident millennial” (read: one of Stiles’ most reliable local babysitters) Emily Stockton. Stiles’ attorney husband does pro bono legal and operations work, and her mom is the pro bono CFO.

“This goes back to when I was a kid and my mom had same problem,” Stiles says. “She was a single mom raising three kids and trying to go to school to get her degree. I remember one time, my youngest brother who was three at the time, had chicken pox. It was during her finals week, she was frantically calling everyone she knew looking for a babysitter. I still remember 35 years later, the panic that she experienced.”

Stiles was eight years old at the time, and nearly 30 years later she found herself in the same panic with a sick kid.

“I had meeting at work and I was trying frantically to get a babysitter to my house,” she says. “I couldn’t get them and I ended up missing the meeting. Fortunately at the job I was at, it was OK and I didn’t lose my job because of it.”

But many Sitter.me users don’t have that kind of flexibility and could risk losing their jobs if a babysitter isn’t available. The company has tens of thousands of users across the U.S., though they don’t disclose exact numbers, and if it continues growing at the rate Stiles expects it to, they’ll hire four more employees in the next year.

“The first one is our director of marketing position,” she says. “That’s the first. Then we’re also looking at a couple of other marketing positions, as well as another developer.”

Stiles says she is open to hiring remote employees and might not limit the search to Colorado-based candidates.

“The whole remote thing, I believe in trust and flexibility and finding the right fit,” she says, echoing a statement that many startup leaders say about culture. “If you don’t trust your employees to work at home, you shouldn’t have hired them in the first place. It takes a particular personality to work at home effectively, but you need to trust employees enough to do that and to be as productive as they can. I think face time is fabulous, but I don’t think it’s required for success.”

Stiles listed the values she wrote in the original Sitter.me business plan: passion for the customer, strive to excel, and trust and respect. She says that she and co-founder Stueve have known each other for years, Stueve and developer Moy previously worked together, and they each have an inherent trust of the other team members to do their own jobs.

“There no micromanaging, no telling you how to do something, we just give you an objective and you go figure it out,” Stiles says. “There’s no ego in Sitter. We’re all about teamwork and trust. You have to be able to take on an objective and be willing to test and measure and fail, and admit when you’ve failed, admit learning and test again. You can’t be afraid of trying new things.”

Stiles says she knows that this type of trust and respect for fellow employees is part of what generates an energetic, productive, successful company culture. At a previous job, she witnessed the deterioration of one company’s culture due to a change in leadership.

“It took the wind out of our sails,” she says. “We went from having so much fun, the Friday afternoon clubs, the camaraderie, the team excitement and will to try, and then everything was standardized. You had to check with 50 different people before you could do something. The bureaucracy came in and it killed the innovation.”

Stiles says that as a leader, she thinks that culture is most successful when employees are able and willing to learn on their own, but that Sitter.me is planning to grow strategically and slowly.

“I believe in growing with the right people,” she says. “It’s very important that we hire people who are the best in their space, and that they really fit with the team. I believe in running lean and mean and only spend when you know that you’re getting ROI. Taking on another employee is a major responsibility. I feel personal responsible for my employees’ welfare and source of income.”

April Nowicki is a contributor at Street Fight.