By: The Mom Project on December 23rd, 2019

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"The Boss of Winnie" Brings Tech to Childcare


Anne Halsall is the co-founder and chief product officer of Winnie, a digital platform that helps parents connect with childcare providers, daycare centers and preschools. She met her co-founder Sara Mauskopf while working at Postmates. “We bonded as the only moms in product, and we’d talk about how few tech solutions exist for parents. It’s a culture shock for millennials. You are used to having an app for everything, but then becoming a parent is like taking a step back in time. So we quit our jobs and started work on Winnie!”

Motherhood has changed Anne’s career in so many ways, both good and bad. “We couldn’t figure out childcare with my first. I didn’t think we could afford a nanny—plus, I had no idea how to find one or manage one. The daycares I could find online were all full. My six weeks of leave ran out and I quit my full-time job at a promising startup because we just couldn’t figure it out. I came back eventually, but took a salary hit and unvested equity. It wasn’t great.” But it was an experience that eventually led to Winnie, helping other parents solve those problems more easily.


“Childcare challenges are many and diverse—cost, availability, quality—but there is also huge a problem of information. A large segment of licensed daycare providers are not online in any meaningful way. Can you imagine searching for restaurants and half of your options don't even show up? What ends up happening with childcare is that the parent — usually the mother — feels like she has fewer options than she actually does. That is a big, big problem. Maybe she would prefer to work fewer hours but can't find a program with part-time options, so she feels stuck in her full-time position paying for full-time care. Maybe she only considers higher-priced centers and ends up leaving the paid workforce because she can't justify the costs. The downstream effects of this information problem on women's health and happiness are significant. We need to fix it.”

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For Anne, “a family-friendly culture is the same thing as an employee-friendly culture. We value impact and results, not hours spent in the office. We use tools like Slack and Google Docs to make it easy to collaborate without being in the same room together. No one is expected to work long hours, and everyone is expected to have a life outside work. When flexibility is baked into the process I truly believe it makes everyone happier and more productive — not just parents.”

“We also offer very good health coverage and cover a sizable portion of the cost for dependents. This is a tough thing at an early stage startup, but at the end of the day we want our employees to feel like they don't have to make compromises to work at Winnie, especially not with their own health or the health of their family. We also are one of very, very few tech startups that offers 12 weeks of paid parental leave for both men and women.”

“I’m lucky I have two supportive partners: my husband and my co-founder. Both relationships are rooted in so much trust and grit and willingness to share responsibility, to take the reins when needed (or ask for help when needed). I can’t imagine doing it without them,” says Anne.

She also mentions that the unique schedule at her children’s school helps her and her husband in their professional lives as well, “Their school day goes until 5 pm, and the day includes a variety of extracurriculars like music, art, and dance. Instead of having to figure out what to do from 3 - 5pm or schlep them around to their activities ourselves, it's all built into their day.”

Startup work is demanding, but so worth it, Anne says, “My oldest son is six and tells anyone who will listen that his mom is ‘the boss of Winnie’ and he is going to work there someday. So I'm pretty motivated to keep this thing going for him!”

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