Office Hours: I'm building a marketplace that's already helping 4M+ parents find childcare. I'm Sara Mauskopf, CEO & Founder of Winnie.Featured

Hi Everyone!I’m the CEO & Founder of Winnie – a marketplace for daycare and preschool helping over 4M parents across the US find child care. I built Winnie after having my first child and discovering a lack of technology to help parents. My background is in consumer products. Prior to founding Winnie, I was the Director of Product at Postmates, and prior to that held product leadership roles at Twitter, YouTube, and Google. I graduated with a Computer Science and Engineering degree from MIT.I’m also a mom of two and currently pregnant with my third child.Ask me anything about transitioning from roles at bigger tech companies to starting my own company, fundraising, finding product-market fit for Winnie, balancing kids and growing a company, or anything else.
It's great to have you join us for Office Hours Sara!Elpha – Please ask Sara questions before this Thursday. She may not have time to answer them all, so emoji up vote the ones you'd most like her to answer.
Hi Sara! I’m curious about how you got from your first 1000 users to 100,000 users, and at which point did you think you found product market fit? There’s a lot of folklore around consumer start-ups which sometimes makes it seem like product market fit is a matter of surviving until a stroke of consumer insight that leads to rapid adoption. Did you follow a steady process of growth to get to product market fit, or did it happen as a sudden insight that led to rapid adoption and exponential growth?
First I'll say I'm giving a talk on exactly this topic of finding product market fit at ProductWorld 2020 if anyone wants a free ticket to the conference: to summarize -- Yes, there was definitely a critical moment for us of figuring out that child care was a big problem we could solve with Winnie. That was truly a key insight for us. Before that, Winnie had a lot of different features and did a lot of different things and people found it useful, but the growth was very much a result of our own effort. It felt hard. We grew but we were also doing a lot to grow -- marketing stunts and growth hacks and features. Once we had found the right use case to focus on and built something that really solved a pain point for parents that was unlike any other pain point in their lives, growth started to happen on it's own.
Thank you! That's really useful to know because I'm at the stage at the moment where growth feels hard and we're doing a lot to grow. As I'm based in Asia I can't make your talk (would love to know if there's a livestream though!!) - could you elaborate a little on how you got to your key insight?
Thank you for the ticket @sm - things like this really mean a lot to junior PMs trying to meet more mentors and learn from the unique experiences of the Bay Area. Much appreciated! I would like to also follow up on the PMF question and ask what metrics did you use at Winnie to build your retention curve and find leading indicators for growth (e.g. daily/weekly actives? or specific actions they took on the app?)
Hi, Sara! Amazing experience. I am the founder of Russian web-service for parents and teachers at the pre-schooling area Now I want to spread our method and web-program to the USA market. What you could recommend as a strategy? We have some sales in Russia, and I suppose, that our method will be evaluated with tutors (toddler and pre-schooling). I am looking for strong partners and going to do some test sales like on this week, sale programs and courses as first to teachers. Thank you forward, Polina Tepliakova.
I'm not sure exactly what your product is because I don't speak Russian but I think if moving to the US or having a local presence here for a period of time is an option, that would be something to strongly consider. We even find that within the US there are so many differences market to market that it helps to first understand each market and what the needs are.
Thank you!!!
I'm russian speaking. this reminded me of Wunder App. check it out!
Thank you for the shoutout @annaarsenault :) Would love to chat with you more about your experience with our app so far!
I really like idea of AI. It is exactly future for early development.
Super! will take a look on that
Hi!Thank you for doing this. I have two somewhat related questions:1. Any advice on how to decide between trying to monetize early in order to show profitability, versus staying free longer to build a big user base and monetize later in a bigger way?2. Any thoughts on building business partnerships with established brands - how to approach this and when?I wonder if you’ve dealt with those questions in building Winnie.For context, I make PuppetMaster (, an app that lets kids animate their arts and crafts, or their toys, or anything they want - just by moving their body or touching the screen.I offer educational art and animation projects through it as well.Thank you!
As far as monetization, it depends on the money you have in the bank. We were able to raise some money in the beginning and run VERY LEAN so we knew exactly how much runway we had and when we'd need to start monetizing or be in a position to raise again. We wanted to be able to focus on building a really useful product for parents and child care providers without having to worry about charging them so we didn't monetize in the beginning and just made sure we had enough money in the bank to operate that way until we reached a scale we could either monetize or raise money.As far as building business partnerships with established brands, this is not something we focused on in the beginning. I think it can be a big distraction for not much value. The exception would be if they are paying you a lot of money.
Are you monetizing now? What kind of revenue are you seeing?
We are! We monetize through daycares and preschools looking to fill their open spaces and build their waitlists. We don't share revenue numbers publicly yet.
Thank you so much for the helpful replies.
Hi Sarah,So pleased to have you here and congrats on the upcoming baby + Winnie. Your second sentence resonated with me so much regarding tech for parents because I found the same thing which is why I'm currently building a platform for the listing and booking of children's activities in the UK (and aiming globally) 🌍. I'd like to know how you have balanced making Winnie a solid business whilst staying true to the original aim of leveraging technology to make the lives of busy parents that little bit easier. I.e. have there been times when outside influences have actively encouraged you (forced 😁) to go down a different route in order to maximise profit and how have you dealt with it or compromised?#FamTechforthewin
I think to avoid outside influences forcing you to do things, you need to make sure you retain board control and ownership of the company as long as possible. One day this may be an issue for us, but I hope that day is not anytime soon :-)
Great! Thank you
Hi Sara!First, I wanted to say congrats on expecting your third baby! I have three kiddos myself and also building a marketplace like you! I had a chance to check out Winnie and love the concept! My kids are past that age but I remember the struggle to find the right pre-school for them to attend. I have so many questions, but I'll just list a few:I checked out your social which was established in 2015. Can you tell me about the growth of Winnie from 2015-2017? What did you do to accelerate that growth and get the word out about your business in the early years?
We started Winnie in 2016. (In November of 2015 my cofounder and I quit our jobs and started hacking on stuff)One of the biggest things we did to grow in the beginning was just launch. It took us 6 months from concept to launch of Winnie in the App Store. It helped that my cofounder and I could both code. Lots of consumer products spend a long time in “private beta” with “friends and family” making things perfect. It was more important to us to understand whether this was a product that had potential and there was no way we were going to get enough usage to understand that in a private beta.By making Winnie public and promoting it both ourselves and via featuring in the app store, we got a good number of people using our product. This is important because we had data to work with. Getting a lot of data quickly helped us figure out if we had product market fit (spoiler alert: we didn't in the beginning)
Hi Sara,Huge fan of Winnie, your "public parenting" on social media, and your hot takes on startups/VCs! I'm a mom of 2 (ages 3 and 1), fellow MIT alum, and founder of Cake (, the digital platform for end-of-life planning. Would love to hear more about your growth strategies and whether the parenting discussions on Winnie have been an effective way to engage people, and if so, how you got those going.Thanks so much!
Go Beavers! (lol that still makes me laugh)My hot take is that forums/discussions are a commodity product. You can find them everywhere. For us, they are useful for keeping parents and providers engaged over time, especially because a new child care provider isn't a thing you need every day and that's ok (but we want to be top of mind when you do need it). On the other hand, we care more about the parents and providers using our platform to actively find child care or fill child care spaces. That's the really high intent, monetizeable activity. So, we allocate our resources accordingly. We do moderate our discussions and keep them high quality, but we also know this isn't the part of the product that is as mission critical right now for us. As a resource constrained startup, you have to prioritize!
Sara where do you get your energy from??!!
I'm one of those people who needs A LOT of sleep. Even when I'm not pregnant, I could literally sleep for 10 hours every night if you let me (I get like 8 hours max now though). Fortunately that seems to be genetic and my kids need a lot of sleep too... so yeah, we all love sleeping in my house.Also, coffee. Lots of coffee. Yes I drink massive amounts of coffee when pregnant and so far (knock on wood) my kids have turned out ok.
Hi Sara! What did you find was the most useful tactic to onboard your first 100 service providers? I'm finding thats small business owners are too busy and stressed to schedule a call or research new platforms.
We took a very different approach with Winnie. We create listings for ALL licensed daycares and preschools and it is free for providers to claim and update their pages. In the beginning none of the daycares and preschools knew about Winnie but now they hear about us from parents who are discovering their programs through Winnie or Google Search and then they come on and claim their page. I learned this from my time at Postmates and their early days -- Postmates also took this approach by just doing deliveries from restaurants and then the restaurants would eventually take note that they were getting orders called in by Postmates. When you're already showing providers value, they come to you.
Hey Sara!I was wondering how you managed the transition from being so close to the product as a technical co-founder In the early days to moving into the CEO role focus as the company grew/went for fundraising? I am a technical founder as well. Also how being a technical founder has helped (or hurt) your progress at Winnie. I should have asked you this when I interviewed you!
I spent my career in product management before Winnie, both as a PM and also managing PMs. When it comes to product and engineering, those have been much easier to delegate as I'm very familiar with how to work with PMs and engineers and designers without doing it all myself. What's harder for me is managing teams and people who are outside what I know. It's hard to hire for a role and manage someone when you really have no clue what that role even looks like! Right now our team is mostly product/eng so I think as we grow and hire in other functions, this is an area that will be challenging.
Hi Sara, congratulations on all that you have achieved so far with Winnie. Curious about what your business looked like when you sought your first funding round? how much do you think your role at Postmates contributed to a successful raise?
When we sought our first "pre-seed" round of around $500k, we had nothing. We didn't even have a pitch deck (though we quickly created one after we walked into our first meeting and realized we were supposed to be presenting something when we pitched). I think at that stage it was ALL about me and my cofounder. We mostly raised from people we knew. I think my time at Twitter helped since I worked there for 4 years and many of my coworkers from Twitter had gone on to become successful investors or angels (and likewise, my cofounder was an early employee at Quora and had connections from there who invested). But my role at Postmates was also instrumental because that's where I met my incredible cofounder Anne Halsall.