Interview with Sara Mauskopf

Sara Mauskopf, CEO and co-founder of Winnie.

Sara Mauskopf is the CEO and co-founder of Winnie, a platform that helps modern parents find local daycare, preschool, and more. Winnie is growing fast with over 2M users in 10K cities across the United States. Prior to Winnie, Sara held product leadership roles at Postmates, Twitter, YouTube and Google. She lives in San Francisco with her husband and two young daughters.

Business Today: How did you start Winnie? Where did the idea come from and how did you discover this void in the market for apps that are for parents which improve their lives?

Sara Mauskopf: Three and a half years ago I started Winnie, and it was shortly after I had my first daughter. I was working at the time, I took a short maternity leave after having my first daughter and then went back to work, and I realized that it was really, really hard for parents and there wasn’t an app for that. So things like finding childcare so I could even go back to work or just figuring out what to do with my child or where to go, that information was really hard to find. And when I asked around and asked other people how they figured out what daycare to send their child to or what to do on the weekend, the biggest thing I heard was you had to talk to other parents and meet other parents and do a lot of networking, and I thought that was pretty crazy because now more parents are two-parent working household. So this millennial generation is more likely to be working, and we don’t have time and we aren’t stay-at-home moms … we also have other things going on. So we have this gap now where all these things that my mom was doing as her full-time job – there’s no one to do those things if both parents are working, and we need tools and technology to fill that gap. And so I was talking to a co-worker of mine, [Anne Halsall], and who now is my co-founder. She has two kids, and she was like “yeah, it’s really hard to get this information. It’s really hard to find childcare. It’s really hard to get information on what to do with your kids and parenting information in general, and we realized that an app or technology could solve this, and we can bring all these information that is locked in parents’ heads online and make it accessible to people.

BT: It seems that Winnie has managed to scale its operations really rapidly and very quickly. The statistic I saw was one million users in 10,000 cities, but I think probably by now it has increased?

SM: We started Winnie with a vague idea of helping parents and making their lives easier, and what we really zeroed in on … was helping parents to find childcare. So of all the information, places to go, and things to do with your kids and parenting information, the thing that was really life-changing for parents and enables them to go back to work, enables them to have high-quality early education for their children, is helping them find daycare and preschool. So in the United States there is no – for the most part – there is no public daycare preschool, it is all private payer, you have to find it yourself, and it’s really hard to find it. There’s not a single place you can go and even see all the daycares and preschools that exist. The crazy thing we found ... is over half of licensed daycares and preschools were not online at all. They are in-home daycares and preschools, so they operate out of the providers’ home. They’re licensed and inspected by the state, but they’re very hard to discover if you don’t happen to know about them. So parents are left thinking their childcare options are very limited or more expensive than they need to be when really there’s great care available if only they had known about it.

BT: You have some past experiences in product management in tech companies like Google, Twitter and Postmates. How has that been relevant to your own entrepreneurship journey so far?

SM: I worked at big tech companies like Twitter and Google, and Postmates – not as big, but now pretty big – and my co-founder worked at Google and also Quora, she was an early employer at Quora. And I think that her Quora background and also my Twitter background were pretty important in creating Winnie, because we saw the power of a crowdsource platform. So I think a lot of approaches in the past, to getting data that parents need, or information that parents need, or solving parents’ problems has been very small-scale. It’s like someone will create a blog and they’ll include a writeup of ten daycares in the city, it’s like that doesn’t scale, but if you create a platform, where parents can review anywhere they send their child to daycare or preschool and providers can come in and update their page across the United States, that can scale to the hundreds of thousands of daycare and preschool businesses. So we saw the power of having a platform like that from our work at Twitter and Quora and realized that we needed to build the technology and not just have the data. It’s important that we have a system that people can update that’s maintained, all that stuff we kind of learned from seeing how Twitter and Quora grew early on.

BT: Winnie seems to be a comprehensive resource for parents that includes listings of daycare, conversation threads on parenting and family activities around town. What is your ultimate vision for Winnie?

SM: The community piece of Winnie is important in that it helps parents stay engaged, so childcare has a longer buying cycle, it’s not buying a dress, where you go online and you find the dress you like and purchase. Childcare is a very considered purchase, and you actually assess your childcare options multiple times for the same child over their zero to five years and even beyond, for things like summer care and breaks. And so it’s important to have a product that is also useful in other aspects of parenting, so we look at the community piece of Winnie and the other supporting pieces like finding playground, parts of playgrounds as really useful in retaining our users and building a brand with them that can be useful in other aspects of their lives. But the real pain point or problem that we’re trying to solve for them is just access to childcare. Helping them find childcare and so we will continue to push on the childcare front, continue to build out our comprehensive data and new kinds of providers. And hopefully over time when we have all the parents and suppliers in one place, that opens up opportunities to offer even new types of childcare that don’t exist today. Like part time or flexible options that are pretty much impossible to find today because all the buyers and sellers aren’t in one place, but if they are, it’s easier to offer this excess capacity that exist. And so you kind of think of it like Airbnb before it was more rigid, what you could book or do. And now that everyone is in one place, offering the excess capacity in their homes, there’s all new types of options for where and how you can stay around the world. So that’s kind of what we see with childcare, we want to bring everyone on to this centralized platform and that will open up the possibilities to do new and interesting things around town here.

BT: Do you have any ambitions to scale Winnie globally or do you want to keep it more nationally-focused?

SM: We definitely want to scale globally, it’s interesting because our app on iPhone you can actually download across the world and also our website of course you can access across the world. So we do actually see people come on from all over and review places to go with our kids and participate in our community. Obviously our data is not robust internationally, but we can already see countries where Winnie starts to light up, and we have some usage which will make it easier when we actually go there and focus on that region. We already have users and data and conversations in those regions to kind of start things off.

BT: So as tech startup founder, what advice do you have for college students who are interested in entrepreneurship?

SM: The biggest thing that set me up for success when I started my company at 30 years old was that in the previous eight or so years, and actually starting in college I had this amazing network. And that network was formed by the people I went to college with and then the people I worked with. And many of those people ended up funding my company and giving me that initial angel investment. Actually there was a group of people that I met at MIT that had put in a bunch of angel investment in Winnie’s initial round of funding so working at great companies, meeting great people, those are really key relationships that will help you later on if you want to start a company. It’s not just what you learn from working at Google. It wasn’t so much like I learnt how to be a great product manager working at Google or working at Twitter. It was more important I met awesome people and impressed them enough that they were willing to either fund my company or come work with me when I started Winnie … Everyone that you meet and work with is potentially someone you might work with or need in the future when you are running you own company. That was something I didn’t understand or value enough at the time, and has turned out to be incredibly valuable now, and I wish I had spent a little bit more time building [and nurturing] those relationships and not just focused on my work output all the time.

BT: What has been the greatest difficulty you have faced so far and how are you trying to overcome it or how have you did you overcome it?

SM: There’ve been so many ups and downs in starting a company. I had kids while I was running this company, [and] my husband was very sick with cancer early on in starting Winnie. He’s okay now, but that was a rough period of time. We’ve had a lot of highs and lows, it’s definitely a roller coaster to start a company. The biggest thing that has kept me going is building something that is really important and meaningful to me. My end goal is to make parents’ lives better to help them find childcare, and it’s not to make a ton of money, and be the most important person in the world. Those might be nice side effects, to be successful, and I think we will make a lot of money, but that’s not my goal and I won’t consider myself successful unless we solve real problems for real parents. Always keeping that in mind and remembering that makes the journey go a lot better so that even when there’s really low points and I really want to quit, I’m like”Is there anything else that I can be working on that would help me reach this goal, could I do that faster somewhere else?” And it’s always no, I have to do this, and I have to continue this because my overall goal is to help parents make their own lives easier. There’s always going to be ups and downs of anything – especially when you’re starting your own company – it’s a really tough, lonely journey but just remembering why you’re doing it in the first place and hopefully the reason you’re doing it is not just profit-motivated but really because you care about making the world a better place in some way that’s important to you.