The co-founders of Winnie: Sara Mauskopf, left, and Anne Halsall (Photo courtesy of Winnie)

Welcome to She Leads, a series digging into the good, the bad, and the ugly of being a woman in business. In each piece, we chat with a different founder about her experiences, the issues women face in business, and how they’re powering through in the face of adversity.

Sara Mauskopf didn’t know she'd be launching a data-powered childcare platform when she left the tech giants for good. All she knew was that she, along with millions of other parents, had a big problem, and no one was trying to fix it.

“I had worked at a bunch of really awesome tech companies with great engineers,” said Mauskopf, who spent time at Google, YouTube, Twitter, and Postmates. “And I just saw that the amazing engineers I had worked with weren't really working on solutions for parents. Actually, no one was working on solutions for parents at the time.”

So Mauskopf, along with her Postmates coworker Anne Halsall, took matters into their own hands and launched Winnie in 2016. Mauskopf serves as CEO and Halsall as chief product officer. To date, they’ve raised $15.5 million to fund their venture. (And they now have two children each.) Childcare providers use their platform to fill their open spaces, build their wait lists, and get support and resources to run their businesses efficiently. Parents benefit from the platform’s detailed listings, which include descriptions, photos, tuition information, licensing status, availability, and more.

The founders’ belief is that childcare needs to be more accessible, and technology is the way to make it happen. Their mission is especially critical in the midst of the pandemic, when the chronic problem of unequal access to childcare in the U.S. has become a full-blown emergency. Mauskopf’s message is now front and center: childcare is vital to the economy, it’s an incredible amount of work, and it’s disproportionately put on women.

We chatted with her about the origins of her company, the blind spots of venture capitalists around women-led companies, and what the pandemic tells us about the state of childcare. Excerpts:

From Day One: The world still sees childcare as women’s work, including much of Silicon Valley. In my years of interviewing female founders, one thing I’ve heard time and time again is that VCs often question the ability of mothers to both run a company and have children, but never fathers. Have investors viewed Winnie as a company only relevant to women? 

Mauskopf: Everything you said has absolutely been my experience. A lot of investors said things like, "I'm already invested in the space." So we'd ask which company, and my favorite was an investor who said he just invested in a tampon company. I was like, "Well, that's not the space we're talking about. We're pitching a childcare company."

Oh my gosh. I’m speechless. 

In their minds, that company was the same because it was founded by two women like us. Tampons and childcare have nothing to do with each other. They’re as different as you can get, but I think that was the perfect example of how investors view a company in the parenting space started by two women. They were like, "This is a company for women. This is a company for moms," when really what we're doing is solving problems for all parents. We don't want women to take on the majority of the childcare burden. It's really important to us that this is accessible to both men and women, because childcare should be the responsibility of everyone.

I can't lie—my jaw is still slightly on the floor from that tampon comment, though I'm not surprised. Just yesterday I was just talking with someone about how investors often group companies that involve women together and consider them a niche. But women are diverse and they aren’t a small, specialized category; they’re half the population and drive 70% to 80% of purchases. 

Another surprising thing was that a lot of investors would ask, "Have you talked to X female investor?" Everyone wanted us to talk to Aileen Lee, who is a really prominent early-stage investor who started Cowboy Ventures and coined the term unicorn. She's an amazing person and we did talk to her, but she doesn't particularly invest in parenting companies. She wants to pick the most successful startups, whether they're founded by women or men. This was even way before she started All Raise [her non-profit dedicated to diversity in funders and founders]. Yet every investor was like, "You must pitch this woman because you're women."

After working at tech giants where diversity is lacking and the bro culture runs strong, how has becoming your own boss empowered you as a woman in tech?

When we started Winnie, it was very important to us that we started a company with a really different kind of culture. We wanted this to be a place where parents could work, where people of all backgrounds would feel comfortable, and most importantly, where we had work-life balance for not just us, but also our employees.

We made it a priority from day one, and it's just been really helpful in a number of ways. We've been able to recruit really top talent who maybe didn't want that traditional work-all-hours-at-this-startup-and-give-your-life-to-this-company environment. Recently, it's also made us pretty adaptable to this pandemic, because we already have a remote-friendly culture that enables people to work from home when they want to.

What do you think this current moment in time with the pandemic says about our society's larger issues surrounding childcare? And can you tell me a little bit about what Winnie is doing to help?

Childcare is essential to a functioning economy, and I think we're all really feeling that firsthand now. This is the message I've been preaching for over four years, and finally, everyone is getting it because they can't work if they don't have childcare. And for the people who need to perform essential work, they can't work from home in the odd hours when their kids are napping. They just can't go into work at all.

We've responded by launching a portal to connect families who need childcare, either to perform essential work or because their state allows them to seek childcare with providers who have open spaces. Over half of the providers on Winnie are continuing to operate either to serve essential workers or to serve any families, and they need to fill their open spaces to continue to stay in business. It's really tricky to navigate, and so we've been spending a lot of time helping open providers operate safely and connecting them with the people who do need their services right now.

Do you think this will lead to a shift in the conversation about work-life balance, childcare, and the disproportionate role women take on?

On an optimistic note, there is definitely a conversation now about the importance of childcare. I'm glad that we're finally really talking about it in the media. There was just an op-ed in the New York Times that went viral and was about the toll it's taking on parents to not have access to childcare in this moment. But on a pessimistic note, I'm very fearful that when there's not easy access to childcare, it's women who take the hit. We’re already seeing that. Women are dropping out of the workforce, taking a step back in their careers, or taking leave from their jobs. How long will it take for their careers to recover from that? That worries me.

Is there anything else you want to add, or advice you’d want to give to other women looking to start their own company?

This is a great time to start a company. It feels like a terrible time, but I think it's actually a really good time. People who’ve had ideas but haven’t wanted to take the leap have now maybe lost their jobs. And the talent that they might recruit is now looking for opportunities. There may not be the same amount of venture funding, but there's certainly enough to get started. The world is changing, and people are rethinking companies that were successful without a second thought. Everyone is starting fresh. It's a good time to start something.

This interview has been edited for length and clarity. 

Sage Lazzaro is a New York City-based journalist covering tech, business, culture, women and diversity & inclusion. Her work has appeared in Refinery29, VICE, Medium, the New York Observer, and more. Follow her on Twitter here.