Alright – so today we’ve got the honor of introducing you to Lynn Perkins. We think you’ll enjoy our conversation, we’ve shared it below.

Lynn, appreciate you joining us today. We’d love to have you retell us the story behind how you came up with the idea for your business, I think our audience would really enjoy hearing the backstory.

When I became a working parent, I was surprised by how difficult it still was to find a trusted babysitter. This was around the time services like OpenTable and other online marketplaces were transforming how people booked restaurants, transportation, and travel. Yet when it came to child care, parents were still relying on email chains, neighborhood listservs, or frantic texts to friends in an attempt to find a personal referral.

In some ways, UrbanSitter grew out of something I had always done naturally: connecting people. Over the years, I had matched friends with great roommates and introduced couples who later got married. After becoming a parent to twins, I built up a list of trusted babysitters out of necessity. Before long, friends and friends-of-friends were coming to me asking, “Do you know a sitter who’s around Friday night?” And often, I did. I found myself making those introductions because I know how hard it is to find a great sitter and how much it means to have one recommended by another parent you trust.

I kept hearing the same frustrations from other parents. Everyone was scrambling when they were in a bind, but there was no easy way to find trusted care when families needed it.
That was the spark behind UrbanSitter. I believed technology could make finding care safer, faster, and less stressful by combining the convenience of booking online with the credibility of personal recommendations and community connections.

What excited me most was that we were not simply building another directory of babysitters. It can be daunting to see a list of hundreds of sitters when all you really want to know is which ones your friends would recommend. We figured out how to use technology to fix that problem. Parents could see sitters connected to their schools, neighborhoods, and social circles, along with reviews from other families. That matters because child care is deeply personal. You are inviting someone into your home to care for your children.

We also believed the opportunity extended far beyond babysitting. Reliable care affects nearly every working parent and increasingly impacts employers as well. Over time, that vision expanded into UrbanSitter’s Corporate Care program, which helps employers provide child care, backup care, senior care, pet care, and other caregiving benefits that help working families balance home and work more successfully.

Great, appreciate you sharing that with us. Before we ask you to share more of your insights, can you take a moment to introduce yourself and how you got to where you are today to our readers.

I’m the co-founder and CEO of UrbanSitter, a website and app that helps families find trusted child care and caregiving services through recommendations, reviews, and community connections.

I spent much of my career in technology and consumer products, but becoming a parent gave me a completely different perspective on the challenges families face every day. That experience ultimately inspired UrbanSitter.
Today, UrbanSitter helps families find babysitters, nannies, tutors, senior caregivers, pet sitters, and household support quickly and confidently. We have also expanded into employer-sponsored benefits through UrbanSitter Corporate Care, which helps companies support employees with child care, backup care, and other family care needs.

What I’m most proud of is that UrbanSitter has become a trusted resource for countless families, while also helping caregivers build flexible, meaningful careers. From the beginning, we focused on creating a service that reduces stress and makes modern family life more manageable.

Reliable care has a ripple effect. It helps parents pursue careers, care for loved ones, stay productive at work, and simply breathe a little easier. Knowing we have helped support families in those moments is incredibly rewarding.

How’d you meet your business partner?

I’d known my co-founders, Daisy Downs and Andrea Barrett, for years before we started UrbanSitter. In fact, before we became co-founders, I had helped connect Daisy and Andrea for a nanny share. Looking back, that feels very true to how UrbanSitter began: one trusted connection leading to another.

Our combination of shared experience, complementary skill sets, and a firsthand understanding of the child care challenges modern families face made us a great founding team.

What made our partnership work early on was that we were deeply aligned on the mission. We were not trying to create just another marketplace. We wanted to build something that genuinely reduced stress for parents and modernized how families connect with caregivers.

There was also immediate validation as we had countless conversations with friends and fellow parents who were all experiencing the same frustrations around finding trusted care. Nearly every parent we spoke with had a story about scrambling for child care or receiving unreliable recommendations. It quickly became clear how universal the problem was. We saw an opportunity to build a platform rooted in trust, convenience, and community recommendations.

I think one of the reasons our founding team works so well together is that we combine personal empathy for the problem with experience building consumer technology products. That balance has helped us stay focused not just on growth, but on user experience and the needs of families.

Can you talk to us about how you funded your business?

Like many startups, UrbanSitter began with a combination of conviction, resourcefulness, and a willingness to take a leap before everything was fully figured out. As experienced entrepreneurs, we knew we wanted to prove our thesis before raising any funding. For example, we agreed upfront that we’d ensure the business had repeat customers before fundraising.

Our early focus was on proving that parents were actively looking for a better way to find trusted child care and that technology could meaningfully improve the experience. We concentrated on building a strong proof of concept and demonstrating real consumer demand.

At the time, caregiving was not viewed by investors as the same opportunity it is today. But what helped us was that the pain point was incredibly relatable. Almost every investor who was a parent immediately understood the stress and unpredictability of finding reliable care. In fact, many of our seed institutional investors were our first customers. Unlike many startups, we did not raise a friends and family round, we went straight to an institutional seed round.

We also differentiated ourselves by building around trusted recommendations and repeat usage from the beginning. Parents naturally share caregiver referrals with one another, and we saw strong organic growth early on because the product addressed a very real need. This made our business compelling to investors.

Like most founders, there were moments of uncertainty. Raising capital always requires persistence, especially when you are building in a category that investors may initially underestimate. But we believed caregiving was foundational infrastructure for working families, and over time that vision proved much larger than child care alone, eventually expanding into employer-sponsored care benefits and workforce support solutions as well.

Contact Info:

• Website: https://www.urbansitter.com
• Instagram: https://www.instagram.com/urbansitter/
• Facebook: https://www.facebook.com/urbansitter/
• Linkedin: https://www.linkedin.com/company/urbansitter/
• Twitter: https://x.com/urbansitter?lang=en