As far as parenting decisions go, choosing babysitters and nannies ranks among the most important— and the most difficult. UrbanSitter founder Lynn Perkins knew she was lucky to find her first two nannies through trusted friends. That gave her an idea. We caught up with Lynn on how her experience as a mom shaped the features that make UrbanSitter so parent-friendly, then asked for some advice on decision making in startups, fundraising and building parent-friendly company cultures. Read on…

Lynn, UrbanSitter provides a clutch solution for everything from finding babysitters for last minute events to hiring long-term babysitters for afterschool pickup. Did you face your own challenges with finding childcare before founding UrbanSitter?

Actually, I was really fortunate finding my first two nannies, and both were through referrals from people I trusted. In fact, I found one of my nannies through a very good friend whose children were getting older. I had seen how great she was with my friend’s children. People would tell me, “You are so lucky to have met your nanny through a trusted friend.” I started to realize how many of my friends wanted to find great nannies and sitters but they weren’t comfortable hiring somebody without a trusted referral. At the same time, I noticed services were starting to leverage social networks to share trusted recommendations among friends. That’s how the idea for UrbanSitter was born.

How did your own experiences hiring babysitters inform the features you prioritized during UrbanSitter’s early stages?

Besides finding a trusted caregiver, the other big pain point I noticed in hiring a sitter was the booking and payment process. Even if I had contact information for four or five great sitters there would be a tedious back and forth over text, trying one and then moving onto the next until I finally found one to book. Then, there was the awkward moment at the end of the night when it was time to pay and I would have to ask them to remind me of their rate and hope that I had enough cash in my wallet. When we launched UrbanSitter, two of the key features we prioritized were online booking and payment.

We love that we can see what groups and schools we have in common with potential babysitters. Did you test other trust-building features, or land on the solutions currently in place quickly?

We started by asking our potential customers how they normally look for sitters. Most said their looked to their close friends, then when that didn’t work out, they’d branch out to their extended network of mother’s groups and parents at school. We believed that by building groups and schools into UrbanSitter, we could mimic the kinds of referrals that happen in real life to establish trust. We do have other features that build trust that were not part of our original plan. One of them is called the “Repeat Families badge.” When a sitter works for a family more than once, we count that as “Repeat Family” and add a tally of these “Repeat Families” to the sitter’s profile as a badge. Parents tell us this is a trust signal since the family felt good about inviting the sitter back for a second booking. We also will show parents and sitters how they are connected to each other through sitters. If I have a favorite sitter and she’s busy during the time I’m scheduling, I can see if any of her sitter friends are available. This also mimics what happens in the real world when a sitter can’t take a job and suggests a friend or roommate for the job.

In early stage startups, so often we spend time and money exploring ideas and solutions that turn out to be wrong for us. What advice to you have for recognizing when it’s time to pull the plug on an idea that’s just not working?

First of all, before you test an idea or solution, decide on the type of results you’ll need to determine if it’s a success or failure. Figure out a way to track that data before you start your test. I’d also suggest building the minimum viable product (MVP) to test the feature or idea before building out the full end-to-end solution. You may learn a lot that will shape how you continue to develop the solution (or abandon it) from this MVP.  

We like to test new ideas manually, before completely building them into the product. For instance, we just launched the ability for teen sitters, ages 16 to 18, to join UrbanSitter. Because this would require many process and product changes, we decided to test the program out in a manual way to start. This allow us to collect data to see if there is enough demand for teen sitters to justify the product work, and see how users are engaging with the process, giving us better ideas for how we would build this in the product than we would have come up with on our own.  

How long you test your solution before you determine it to be a hit or a miss really depends on how much volume you are doing and whether your business has extreme seasonal peaks and valleys. You wouldn’t want to test a new feature during your naturally busy season because the seasonality may skew your results. Ideally, you’d test your solution on some users and show other users the previous version to get a real apples-to-apples comparison, but I know this is not always an option for small companies.

There’s a lot of talk about how fundraising as a mom can be especially difficult. You’ve done it successfully. Any fundraising advice for other moms?

First, decide on the type of financing that’s right for you. There are lots of ways to raise capital from small business loans to crowdfunding to venture capital. Before you make your pitch, do your homework. That means finding the sources most likely to give you funding in my case, I sought out venture capital firms with a track record of backing female founders or marketplace businesses like mine. It’s also important to back your big vision with big numbers to describe the opportunity or problem you are tackling. As you can imagine, most of the firms I encountered were all males who had never booked a sitter. If yours is a product or service that the investor wouldn’t use themselves, it’s important to get them excited about the size of the opportunity and the reasons why you are the team to build this and why your solution will win.

How does the fact that UrbanSitter is a parent-focused startup impact your company culture?

Since many of us are parents, flexibility has been a major pillar of our company culture. We’re supportive of work-family balance, so leaving the office early for a school event or working the morning from home to take your child to the dentist is completely understood. In fact, we’ve made it a company goal to find tools and processes that make remote working even smoother. While we aren’t focused on facetime, everyone is expected to work responsibly toward their goals. That could mean logging on after the kids are in bed or choosing to work early mornings in order to better accommodate your personal schedule later in the day. We put a lot of trust into our employees to do what works for them-and that tends to attract great talent.  


Now, a few rapid fire questions on how you find balance. Beyond UrbanSitter, what are a few of your favorite time-saving apps?

Instacart, Caviar, and Zum

Your favorite way to spend time with your kids?

Outdoors, ideally at the beach or skiing. Bonus, if they are all getting along with each other.

Your best advice for dealing with setbacks?

Put out any urgent fires the setback has caused, take a deep breath or even leave the issue overnight, and think through strategies to resolve the setback when you have time to think clearly. 

3 pearls of wisdom


Recently my two older children have been asking me a lot of questions about my business and have started talking about the types of businesses they would like to build. They’ve even commented a few times on how they like hearing about my business. I’m starting to see the positive impact I’m having on my children as a career mom. When my kids were younger I carried a lot of mom guilt about how much I was working and I felt torn about it, even though in my gut I knew it was best for both my happiness and my family’s overall well-being. I mention this because I know there are a lot of moms of young children who are feeling the same guilt and torn feelings.


Getting your kids to work as a team makes everything easier. I used to dread the morning routine. Getting three boys ready for school presented many challenges. Things became easier once I told the boys that they’re a team and the team has a specific list of things to do every morning before any of them can play before school. This includes doing things like putting on clothes, packing backpacks and brushing teeth. They can complete the list however they want, but the list has to get done and done for all three of them. My youngest can’t put on his clothes unless they’re laid out for him face up, so my older boys know they need to get his clothes ready for him. They’re motivated to help each other because they don’t want to let “the team” down.


This third piece of wisdom is really more of a mom hack than wisdom. Like most busy moms there are times when I have my children with me and we need to quickly run into a store to get a birthday present. Inevitably, this results in a free-for-all of “Mom, can we get this?” Instead of risking a meltdown by saying no, I take pictures of the things they want to “save for their birthday or Christmas wish list.” I make a point to review the photos with them before holidays and birthdays. Works every time!

xx Lynn Perkins
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