Boss Moms: Sara Mauskopf and Anne Halsall, Co-Founders of Winnie

Laura Spaventa Lewis
Unusual Ventures
Published in
13 min readOct 1, 2019


Editor’s Note: Welcome to the Unusual Founder Spotlight series! The goal of this series is to introduce the technology founders in our portfolio who have the rage to master and are currently building the future across categories and industries.

Gone are the days when women are expected to kiss their careers goodbye to stay at home and raise the kids. In the US, dual-income households have grown from 48% in 2015 to 63% in 2018 and more women are participating in the workforce than ever before. Although the US child care market has grown 4% per year since 2014 and has become a $57B market, the supply can’t keep up with the demand spurred by the shift in workforce trends. The changing workforce coupled with the growing awareness of the benefits of early learning have severely limited parents’ options to find quality education and care for their young children.

Sara Mauskopf and Anne Halsall, co-founders of Winnie, met while working at Postmates and commiserated over the struggles that they were facing firsthand as first time and second time moms. Recognizing that the pains facing working parents, particularly working moms who usually shoulder the burden of finding child care, would only increase as more millennials started having children, Sara and Anne realized they were onto something. Sara and Anne also recognized that they were uniquely equipped to solve America’s growing child care shortage due to their technical backgrounds and the unique resources that were at their fingertips in Silicon Valley. And so, the co-founders decided to quit their jobs and start Winnie, a marketplace for child care, in the beginning of 2016. In less than four years, Winnie has connected over 3 million parents with over 150,000 providers across the United States.

We recently sat down with the co-founders to understand why they felt the need to tackle the growing child care problem in the US, what keeps them going through the inevitable bumps in the road, tips they’d give aspiring entrepreneurs, and why their kids are their biggest fans.

Unusual: Can you give us a little background on yourselves?

Sara: My background is in product management, so I’ve been a life-long product manager and have always approached things from the product and engineering angle. Prior to Winnie, I was at Postmates as their Head of Product, and also was an early employee of Twitter, Google, and YouTube. There are some people who are serial entrepreneurs or people who knew they wanted to start a company their whole life — you know, the people who started lemonade stands as kids. I was not one of those people. I’m very much a hard worker and I like to have a boss who tells me what to do, so I can meet those expectations. That is very much my personality and I actually never saw myself starting a company. But I was working at Postmates at the time I had my first daughter and I saw that it was very difficult to be a working parent, and do basic things like find child care. It felt like no one was working on solving this problem I was facing firsthand as a working mother and I thought, if I didn’t do this, who was? There I was, further along in my career, with access to capital and great talent. I have an engineering background, so I could build a lot of the product myself. I met Anne around this time, who had experienced the same issues as me. Her determination and confidence in our ability to solve this problem gave me the courage to do something completely out of my comfort zone and dive into Winnie.

Anne: I’m a consumer product designer at heart, and I specialize in mobile products. I started my career in technology at Google, was an early employee at Quora, and went on to do product design at Postmates, which is where I met Sara. My interest in knowledge sharing and local products all came together when Sara and I started talking about information problems facing parents. Couple that with the personal struggles I felt as a mother and the strong drive I’ve always had to be an entrepreneur — this is not uncommon among people who work in product — I was very drawn to solving this growing child care problem.

Unusual: Can you give us an overview of Winnie?

Sara: Winnie is a marketplace for finding daycare and preschool. Parents can use our website or mobile apps (iOS and Android) and search every licensed daycare and preschool in their area. Winnie offers detailed information like: whether the program has availability, what ages they accept, whether they are licensed, how much it costs, etc. On the flip side, childcare providers use Winnie to do things like fill their open spaces and get in front of parents. In many cases, Winnie is their first online presence. In the process of building Winnie, we discovered that over half of licensed daycares and preschools were not online at all. So, just by building this resource we’ve allowed parents to connect with all of these childcare programs that they did not even know existed. Currently, we have over three million parents across the United States accessing our platform, over 150,000 providers across the country utilizing Winnie to fill their childcare programs, and help over 500,000 parents find childcare each month. | Anne Halsall and Sara Mauskopf

Unusual: Sara, you touched a bit on your “aha” moment that led you to start working on Winnie, but could you dive into that moment a little more?

Sara: I think the big “aha” moment was when we both realized that the problems we were facing as working mothers were not all that unique and was actually a trend with millennials. 63% of households in the United States are dual-income and Anne and I faced this firsthand and realized that this was only going to be more of a problem as more millennials started having kids. While I realized I wasn’t so special in terms of the problem I was facing, I recognized I had the capabilities to solve this problem. That for me was the true “aha” moment: it’s not that the problem I’m facing is unique, but that I’m uniquely positioned to build something to fix the problem.

Anne: I had my “aha” moment a little before I met Sara, when I had my first child. After giving birth, I had this experience where I had difficulty breastfeeding and the first thing I did in the maternity recovery room at the hospital was jump on the App Store and search for a breastfeeding app. In the hospital, they give you this book where you’re supposed to write everything down and I thought, “F that. I’m going to find an app and make this easier.” I quickly found there weren’t really any options, and the options that were out there were made by men who had never lactated before, and didn’t understand what a lactating mother experiences. And I felt, almost in my soul, so offended and upset that this is a thing that half the population does or will do, which is so important to the health of both the baby and mother, and yet it was invisible to the world of software. That was the first “aha” moment where I thought, “Oh, right — I just became a mom for the first time, and the world of technology I was used to as a millennial doesn’t exist in service of my needs as a mother.” I ended up quitting my job and working on an app to track breastfeeding while my son slept, because I felt an entrepreneurial drive to fix that problem. I thought, “It has to be a mom — it has to be a woman — who actually experienced this problem.” And then I felt that bubble up again when I met Sara and started talking about the issues she was experiencing as a first time mom. At that point, I had two children and more knowledge of motherhood and knew it wasn’t just about breastfeeding, it’s not just about raising a baby — it’s everything.”

Unusual: Getting a company up and running is not easy. Have you ever thought of quitting and if so, what stopped you?

Sara: Good question. I think we’ve built an incredible culture, so that we could sustain this company and work on Winnie for a really long time. That said, I personally did think of quitting early on. We had not raised money and had just gotten started when my husband was diagnosed with cancer. Between the diagnosis, a new baby, and trying to get a company off the ground, I was pretty overwhelmed. I thought, “We are not too far in, we can just throw the towel in at this point.” I took a couple of weeks off to figure things out with my husband and get my personal life together. When I came back, I found that Anne and our small team had been running things better than when I was there. Everything was chugging along smoothly — they had built the first version of Winnie’s app and were ready to launch it in the App Store. That was the first moment where I realized I wasn’t the end-all, be-all of the company. In fact, we had done such a good job of setting up a sustainable culture early on that did not require any one person to be working all the time — or even be available for extended periods of time — that I could take the time I needed to get my husband healthy and the company was going to be fine without me. So any time now that we’ve hit bumps in the road or things have felt tough, I always just think back to how I felt then and remind myself that we got through that time. Every other problem is easy, especially when you have someone so close to you so sick — it just puts everything into perspective. It’s like, “Oh, the product didn’t do well.” Or, “X metric went down.” It’s no big deal — no one is dying. I think I would have taken a lot of things more personally, but I always have that time to look back and think, “I got through that.” None of this other stuff fazes me at this point.

Anne: No, I never thought about quitting. Things change, life goes on. I think that one side effect of seeing it as a long journey that you want to work on long term is that you have to do it in a way that’s adaptable to the inevitable things that happen in life. Especially when you have a family — things happen and change quickly and you need to be ready. But, I am also an optimist and very, very driven to work on this vision and will do so as long as I possibly can. I feel privileged and honestly, lucky to have the opportunity. The desire not to screw it up and really make the most of this opportunity we have been given is the driving force that continues to get me out of bed every morning. Not to mention knowing that we’re making a big difference in the lives of families with children. I couldn’t imagine quitting — I’ve never had that feeling. Failure of any kind just feels like another bump in the road.

Unusual: You often hear about the glamorous side of entrepreneurship, but what about the flip side? What has surprised you the most and/or been the hardest part about being entrepreneurs?

Sara: We are pretty authentic people and there are probably zero parts of entrepreneurship that are glamorous. The thing for me that I didn’t expect was the amount to which it’s not really about my capabilities. It’s more about my ability to prepare and put in place an incredible crew of people. You hit a point pretty quickly where it’s not about what you can execute, it’s about who you put on the team. I think that’s actually been our super power — we’ve attracted this incredible talent at Winnie and have retained the talent. We have some employees who have been with us since the beginning, which is so rare for an early stage startup (we’ve been around for 3 ½ years.) The reason I think that’s been the case is because we built a culture where we really live our values of being family-friendly.

Anne: I absolutely agree with Sara. When Sara and I were first starting, we were like, “We’re such cool and impressive people, we have such great backgrounds!” You feel that’s so important, but you very quickly tap out what you personally can drive. And when you have a huge vision like we do to help every family who wants access to daycare and preschool, you have to have a great team behind you. That can be a very different kind of work than what you’ve done to get to that point, so there’s a learning curve there. However, your ability to execute on building and retaining a great team is the single most important skill that you need as an entrepreneur.

Unusual: For entrepreneurs who are just starting out on their journey, what’s the biggest tip you would give them?

Sara: Don’t wait. There’s two parts to that. If you have an idea and it’s something you want to work on, there’s no better time than now. There’s nothing you need to learn before you dive in — you’ll figure it out. The second part has to do with living your life. If you want to start a family, start your family now. You don’t have to wait until you raise money or wait until you hit a certain level of success. You can do it at the same time and it will only make you more effective. I’ve found that every child I’ve added to the mix has only made me better. I really, truly mean that. I’ve become more effective as a leader, better at prioritization, the company has done better, and we’ve raised more money — literally with every child. Don’t wait.

Anne: My tip is a little more practical — don’t fundraise if you don’t have to. I think a lot of people feel like they have to go out and raise a bunch of money before they can really tackle whatever it is they are building. That’s true for some things that you may want to build, but certainly not for all of them. Indeed, if you focus on value-creation and revenue-generation earlier, that makes fundraising much easier in the future. Some of the discipline that you might acquire from bootstrapping will actually help you with capitalization. I meet with a lot of young founders and usually the first thing they ask is, “How do I go out and start fundraising? I’ve got my deck and my idea.” I almost always ask if it is at all possible to take the next step without raising funds. Raising huge amounts of money isn’t a goal, but it kind of feels that way sometimes — it feels like your metric of success as a founder. Really try to avoid that mindset as much as possible.

Sara and her family

Unusual: What did your family say when you told them you wanted to quit your job and start a company?

Sara: At the time, I only had one member of my immediate family who could talk and that was my husband. He was super supportive from the beginning. Having a supportive partner who takes the lead on child-rearing has been really key for me. Great childcare is the enabler and I have that in a partner, I have that in a preschool. Now that my oldest daughter is four-and-a-half, it’s pretty amazing to hear her talk. She thinks all moms are CEOs and that’s just what moms do. And that dads take care of kids. It’s awesome. If nothing else comes out of this, I have the fact that my daughters think it’s perfectly normal to have your mom build a company. Watching them observe this and take it all in is pretty much all the reinforcement that I need to know that I’m doing the right thing. They obviously couldn’t be supportive early on as babies, but now my kids are my biggest supporters.

Anne and her family

Anne: My husband always thought this was the greatest idea ever and in many ways — subtle and not so subtle — encouraged me to go for it. He is definitely a big component of the confidence I feel knowing that he believes in me and was supportive of doing things that impacted our family like quitting my job without a salary for a while. He also did some stay-at-home dad-ing when we were fundraising and having the peace of mind that he was taking care of our family during that time was so helpful. I have two little boys and they say all the time, “Mommy’s the boss!” They’re both really excited and proud of what I do and what I have accomplished. My older son is convinced he’s going to work at Winnie one day and even has the Winnie app on his iPad. I don’t know exactly what he does with it, but he thinks it is the coolest thing ever that I make apps — it’s so magical to him. Not only do I feel very supported by my family, but it is very cool to see that my kids relate to me that way and they don’t feel like they are missing out on anything. They’re happy that I’m doing what I’m doing and they’re very proud of me.

Learn more about how Winnie is helping connect millions of parents throughout the US with high quality child care