Lynn Perkins: The Mommy Entreprenuer

The start-up veteran made life easier for moms when she launched a company while taking time off to be with her children

By Katrina Brown Hunt

In 2011, Lynn Perkins took a break from the tech world to spend quality time with her small kids. In doing so, she came up with her next start-up idea—and got a unique insight into her future customer base. “I had connected with the mom community,” says the Bay Area–based CEO of UrbanSitter. “These mom groups had these online lists, looking for sitters or nannies. I found it fascinating that people would take advice from the people in this group—that they felt less guilty leaving their kids if they had some connection to that sitter.”

Not long after that, UrbanSitter.com was born, a website where members access child-care referrals through common connections and groups—schools, playgroups, swimming programs, and more. (Sitters, meanwhile, are vetted with multiple levels of background checks, including social media use.) Today UrbanSitter.com is available in more than 60 cities in the United States, with a field of 150,000 sitters and nannies.

The company has benefited not only from Perkins’s connection to mom groups, but also from her background in start-ups, like the fashion site she founded, Xuny, as well as her stint as director of real estate development for Joie de Vivre. Diversity Woman spoke with her about the wisdom she’s gained from both big and small companies—from how to shop for real estate to the upside of being fired.

Diversity Woman: What made you think UrbanSitter would work?
Lynn Perkins: I’ve always loved to match-make—spouses, jobs—so I had become this nanny-babysitter matchmaker for my mom friends. I knew my next thing would be in tech, where we were seeing more peer-to peer transactions, like Air-bnb, and tech companies using customers’ social media profiles. If there was ever a marketplace ripe for using this kind of innovation, this was it. I ran the idea by a few programmers, and one dad said, “Sure, I can do this.”

DW: What were the challenges in launching the business?
LP: I was starting the company at a different point in my life, when I had two young kids, so it was both crazy and exhilarating at the same time. And in the beginning, pitching UrbanSitter was tough because the investors were typically men, and they were more removed from their child-care solutions—making those decisions often falls to women. It’s tougher to pitch to an audience that doesn’t use your product.

DW: What did you learn in the process?
LP: One thing I had always assumed was that if you booked a sitter—say, you wanted Stacy from UCSD but she’s busy—you would want to go back to your connection with a friend and see whom she would recommend. But if you have had a good experience with Stacy, you want to book her friend, like her soccer buddy. That’s been really interesting, the way we can surface the connections—the same way parents are connected through organizations, so are the sitters.

DW: Growing up, were you a natural leader?
LP: I grew up in San Diego, and I think I always knew I wanted to start a business. As a kid, if our house was getting shingles, I would create a firewood business. In high school, I was even a babysitter broker—parents would call me—and I also babysat. I liked organizing things.

DW: You’ve spent some time working for large companies. What did you learn from them?
LP: At a big company, you’re always acquiring skills, whether you stay in that field or go into something else. I get told by investors a lot that our presentations always look professional, and you can’t underestimate that. Having that thorough training, on basic business fundamentals, instills confidence. At big companies, I liked working for really smart people—a boss who inspires. But what I didn’t like was feeling like a cog in a big wheel.

DW: What strengths have you gained from being involved with start-ups?
LP: You have to be gritty and scrappy in a start-up. For instance, at UrbanSitter, four years ago we were looking to get a new office, and the real estate climate had gotten crazy. I knew I needed engineers, and they like to work in nice offices—and I was seeing either dingy spaces or ones outside my budget. I started looking at the tech publication TechCrunch, in the mergers and acquisitions section, to see which companies were acquiring other companies. I’d call the bigger company’s leasing department and say, “You’re about to get this space on your books, and if you’re going to sublease it, I want to hear about it, and then you won’t have to use a broker.” I saw that a company was being acquired by Oracle, and we got that company’s space at about 60 percent of the rate at the time. Then, when the Oracle team came to look at the office, they sold me all the furniture for $1. The money I saved bought us another engineer.

DW: What was your very first job?
LP: I worked at Baskin-Robbins when I was a sophomore in high school, and it was such a humbling experience: I got fired. A group of kids had come in with gift certificates for sundaes, with their parents, and I accepted 10 fake gift certificates. I was fired in front of the coworkers at a meeting—it was humiliating.

DW: Were you bitter? What did you take away from it?
LP: I was pretty upset, but it was a learning experience. Later on, I had a boss who was kind of intimidating. But then I thought, the worst thing that could happen is he’ll fire me. And I’ll go on. So I guess it taught me resilience. The funniest part was, at the time, I didn’t even eat ice cream, so I saved them so much more than what they lost on those gift certificates.

DW: What do you look for when you interview?
LP: I look for grit and scrappiness, and 
I like people who are curious. At a start-up, you’re constantly testing whether something is working or not. I have a quote on the wall, from an interview I did with an investor, and I always get asked about it. It says, “As You Develop Trust, You Develop Brand Equity.” People always ask about it. For people who are interviewing, what we’re doing is building trust on both sides. I want people who work here to trust the company as much as child care is based on trust.

DW: What piece of business lingo annoys you?
LP: One that drives me crazy is pivot— it’s used all the time. In one way, it can mean something wasn’t working and you had to change directions. That can be great, and it’s important to course correct, but pivot sometimes just sounds better than saying that you’re failing.

DW: What book have you read recently that inspired you?
LP: I read Turn the Ship Around! by L. David Marquet, who while in the navy was put in charge of a sub. He becomes an expert in this one submarine and then gets assigned to a totally different one. He has to learn how both to manage a giant group and also to get them to teach him things that he needs to know.

I am not a programmer, so it’s good to think about how I have to manage people who have expertise that I don’t have. How do you get people to follow you, and also have them rise to the occasion? DW

Katrina Brown Hunt is a regular contributor to Diversity Woman.

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