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Meet Carefully's Founder, Leslie Borrell

After 20 years at leading tech companies, Leslie Borrell launched a childcare platform to support parents how and when they need it most.

Where are you from? Share a little about your family’s story.

I was raised in Houston, Texas, and I identify with my dad’s Cuban roots as well as my mom’s Jewish family. We celebrated holidays culturally but not religiously. I say I’m “Juban,” which means we yell a lot!

My grandfather came over from Cuba as a boy, and he later started his electric company in Tampa with a $50 tax refund. His oldest son—my uncle—turned it into a multi-million dollar business. My dad and his other brother became doctors. My grandfather was an immigrant and worked hard. It’s a quintessential story about coming to America and wanting a better life.

You’ve been solving problems with technology for nearly two decades. Can you share an example or two?

I have a tendency to gravitate to big, messy problems that drive changes in how we work, think, and build technology. Because when things are in chaos, people are more open to change.

At Travelocity, my team took the first steps in breaking up the company’s massive, antiquated travel technology platform. I then took the lead on building out their new “Global Platform,” which was as much about encouraging people from different companies around the world to collaborate in new ways as it was about getting very different systems working together.

While Travelocity was about creating a new platform out of an existing one, my work at Amplify focused on building from the ground up. As VP of Engineering, I was tasked with creating a tablet-based educational platform that would be used at schools around the country. Both of these projects involved hundreds of people working over many years, with many successes and failures—and lots of learning and growing.

Your son, Aidan, was born in 2012. He’s a big part of the reason you founded Carefully. Did you have any sense of how hard childcare could be before you became a parent?

Most of my friends didn’t have kids, and my colleagues didn’t either, so I didn’t have a lot of personal experience. My baby sister was the first to have a kid in our family, and she’s a stay-at-home mom. My mom stayed at home, too. Part of my experience is that females in the family stay at home to take care of the kids. I obviously respect it a lot, but that was never something I considered.

How did you navigate childcare?

Aidan’s dad has not ever been in his life, at least not for very long. I’m the kind of person who just figures things out—I have resilience, fortitude. I also recognize my privilege, having always had the support of my family, and having the salary and benefits of an engineering executive job. Though my family didn’t live nearby, I was able to afford a nanny share, and I had access to backup care benefits from my employer, which I fully utilized.

When my son started preschool, I continued paying for sitters to support my work schedule, which meant I rarely picked him up from school or got to know other parents. It was tough to rely on a caregiver for so many hours, both emotionally and financially, even as someone making a very good salary. As important as the caregivers were in our lives, I was still a single parent who was trying to figure out how to pay for all our childcare needs every month.

You had access to childcare that you trusted, and you could afford it. Still, you struggled.

Realizing that is part of the reason Carefully is so important to me. I was able to afford childcare, but I was sacrificing all this time with my son. It’s a tradeoff. You want to be able to make those choices rather than being forced into them. Sometimes you can’t keep your job because you can’t afford or find care, and sometimes you’re handcuffed to your job because you need it to afford care.

How did Carefully start?

It was 2016. I was between jobs, and two things happened. First, I was in a Facebook group for moms in my area, and they were starting a care circle sign up sheet in Google—for 5,000 parents!

"Through life I found Carefully, and through Carefully I found a better way to live."

Second, I invited one of Aidan’s friends over for a playdate. I assumed his mom would drop off her son, then pick him up later, but when Aidan’s playdate arrived, his mom didn’t leave. She stayed the entire time. So instead of getting a few minutes to take a breath while the kids played on the living room floor, I found myself entertaining another parent—who I was sure had errands to run or something better to do. That’s when I knew I should start Carefully.

What is Carefully all about?

At Carefully, we envision a world where parents can seamlessly move from organizing playdates with their personal network, to signing up for after-school care with a trusted local business, to being a quick click away from picking up a shift at their employee sponsored childcare co-op. This is the world that I want to live in, and it starts with an appreciation for community-based care. When you help other people, you help yourself.

What’s it like using Carefully?

We’ve tried our best to create a neighborhood feel on Carefully, so you are welcomed into the community with each step. You might come here between naps or meetings, but you’re here because you need to connect with your community for childcare, playdates, and support. In just a few steps, you can start or join a group with people you know and trust.

Pretty quickly, you realize that Carefully is not like other social networks. It’s made for families and focused on caregiving, so there isn’t lots of distraction, which our members appreciate. Once you have a few connections, you can start organizing care circles, babysitting co-ops, playdates, and events.

I’m excited about our newest offering, which enables universities, employers, and community-based organizations to offer Carefully as a benefit to their members and workers. This is really important. As of March 2022., 89% of all U.S. workers did not have access to childcare benefits through work.

Longer term, we’re building out our small business network to surface events, classes, and activities, which we see as a great opportunity to support the growing class of Mompreneurs taking ownership of their careers (and schedules).

What’s it like using Carefully for the first time as a parent?

Our hope is that you have a sense of joy, relief, and connection. People often have one or two friends they’ll always ask to watch their kids when they’re desperate. With Carefully, you’ll expand your childcare options to second, third, and fourth degree connections, giving you a reliable network to tap into. You’ll never be desperate to ask for help again. And once you start hosting and attending care swaps, you’ll feel excited to discover a picture from your child’s playdate, or an invite for another playdate, or a care request to help someone else in your network.

Once you start using Carefully and inviting others onto the platform, you’ll also feel less alone. You’ll realize how many other parents near you are there to help—and how helping each other creates a sense of connection and trust for everyone.


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