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Scaling a Product While Building a Community

Sara Mauskopf, Co-Founder & CEO, Winnie

I’ve got 99 problems, which one do I solve (first)?

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I’ve got 99 problems, which one do I solve (first)?

While this isn’t exactly the question Sara Mauskopf had when she first became a parent, she did have an influx of questions with no good answers. As many product people do, she decided to find a solution. Thus the creation of  Winnie, a platform to make parents’ lives easier through childcare resources and community. 

When she launched the company, Sara and her co-founder lacked focus because there are so many problems to solve with parenting. As they developed and launched the platform, they found the area parents needed the most help is childcare. 

How did they know to make the change and shift the focus? You’ll find out what factors they considered and how listening made all the difference. 

Read the full transcript below.

Sara Mauskopf: We understand that stuff has to be instrumented, and it's almost never the thing that you expect. And you have to do user research and you have to really go deep in understanding the data that's being presented to you.

Anna Eaglin: This product-

Christian Beck: Are we recording?

Anna Eaglin: Oh my God. [inaudible 00:00:17].

Anna Eaglin: Better Product, the only show that takes a behind-the-scenes look into how digital products are created-

Christian Beck: The businesses built around them, and how you too can innovate better product.

Christian Beck: I'm Christian.

Anna Eaglin: I'm Anna.

Christian Beck: Welcome to today's show.

Christian Beck: Being a parent is pretty life-changing. I mean, you did just bring a new life into the world, and there's this moment where you kind of step back and you're like, "Okay, so where's the how-to for this kid?"

Anna Eaglin: And that's really where Sara found herself after having her first daughter. She had many questions and not a lot of answers. So how do parents figure this whole thing out?

Christian Beck: Wait, are you asking me? Oh, no? Cool. Got you.

Anna Eaglin: Sara Mauskopf is the CEO and Founder of Winnie, a platform to make parent's lives easier through childcare resources and community. She worked at three notable product companies, Twitter, Google, and Postmates before building Winnie.

Christian Beck: As a new mom and working parent, she quickly realized as Anna said, nobody really had the answers to her questions, it was sort of, "Eh, you'll figure it out," kind of approach.

Sara Mauskopf: This is crazy. I'm working, I'm busy. I don't have time to do all this extra work. It should be easier to get this information. And the more the two of us started talking about it, we realized that this new generation of Millennial parents, we have different expectations. We're busy, we're more likely to have two-parent working households, less likely to have a stay-at-home parent who's doing all of this mental work.

Anna Eaglin: So starting out, the vision was simple, help parents find the answers to their questions.

Sara Mauskopf: It really took building the product and seeing how the community started using it to really hone in on the thing that we could do that would change lives. And for us, that thing was helping parents find daycare and preschool. We just found that childcare was a bigger pain point than pretty much everything else we were imagining. It was the thing that without it, you couldn't really do anything else.

Christian Beck: Finding product market fit is obviously critical, but often founders struggle with the balance of wanting to do everything, instead of focusing on what it is the users really want.

Sara Mauskopf: It took us a longer time than I would have liked to realize that we needed to focus on the thing that we need to do better than anything else that was out there.

Anna Eaglin: Let's stay on that a minute. Sara mentioned it took her getting hit over the hear multiple times, metaphorically of course, before they realized focused on just the childcare component of Winnie. So how did they get to that point?

Christian Beck: The NPS?

Anna Eaglin: Yes, that's what she said.

Sara Mauskopf: We started measuring the NPS, the Net Promoter Score of our users who were doing different things with the product, and we discovered very quickly that the users who were finding childcare with Winnie had a ridiculous NPS of like 70, which is like on par with Apple products.

Anna Eaglin: So when Winnie started, the platform contained a plethora of features for parents. Then they shifted the focus primarily on childcare, yet they didn't get rid of the other things that made up the product, things like where to nurse, family-friendly restaurants, and just straight up Q&A. Keeping these components kept parents coming back to the platform, even after they'd made childcare choices.

Christian Beck: Building the community is also what keeps the product top of mind in terms of retention and user engagement. So yes, the product focus shifted, yet because they sought to serve parents, there was already an engaged audience in place. But how do they actually get that community? Well, that's the rest of the story.

Sara Mauskopf: Yeah, so initially, it was we actually didn't have a website. It was just an app. And we were kind of fortunate in that very early on, we were featured in the App Store and we got a bunch of early users that way. But I think we, the growth tactics that worked for us back then when we were much smaller were almost I wish they hadn't worked so well, and I wish we were forced to develop the sort of scalable engine earlier. And for us, that scalable engine has really been the content, like the content is what really drives the usage, whether it's people coming in because they hear we have great data on childcare or people actually just finding us because they're doing a search on Google and we now rank for all of this content. And the earliest users who found us through word of mouth or through me tweeting or getting featured in the App Store, like all these sort of tactics to get our first users, they only work for the first 100,000 users. And after that, you have to have a scalable engine that delivers you 20% month over month growth in order to really have a sustainable product.

Sara Mauskopf: And you can't fake that. Unless you're going to buy those users, and we weren't because we don't have the funds to do that.

Christian Beck: So on this community notion, we've talked to a few people that are working on building out communities and I think what always... The question that's always in the back of my head is, once you build a community-driven platform where the content is driven by the community and sustains it, what do you as a product person in growing revenue and growing user base, what do you focus your road map on? What does it look like?

Sara Mauskopf: I think the community is not enough. And the community still really is a commodity. We have a bunch of differentiated aspects of our community, the fact that it's not just parents but also caregivers, the fact that you can do things like post anonymously, that you can't do in other places. But the real important way that we get users is through the utility, which for us is primarily our childcare search. It is the thing that does not exist anywhere else, there is no competition, there's nothing that even comes close, it's a massive pain point. We don't have to prove its value to anyone. They're already searching for this thing, we just have to be there at the top of results. And so we focus really all our effort on improving that utility, like making our childcare search more comprehensive, better, getting more providers on our platform, getting data on their availability and whether they have open spaces that no one else has, and making that information really easy and accessible and pushing it to people.

Sara Mauskopf: Those are the things that are critical for getting us users. And then the community keeps them around, it keeps them engaged, it's sort of a bonus, a nice bonus, but it is not a primary thing that attracts users to Winnie, the primary thing is people have this massive pain point in their life where they need daycare and preschool.

Anna Eaglin: A lot of founders that we've talked to originally built their products based on a problem that they had. At what point do you kind of stop trusting yourself to know exactly what your users want because you are your users, and start to kind of look more at what people are starting to tell you? Or has that shift ever happened for you?

Sara Mauskopf: So I think it is pretty important that we have founder market fit, which is what I would call what Anne and I have, because we have kids and we've faced this pain point ourselves, and so we understand it very viscerally. My co-founder Anne even dropped out of the workforce for a period of time because she could not find childcare, and so she knows what happens when you don't find quality childcare. And I think that is important especially when you're a founder, because there are so many ups and downs of building a product, and there has to be something that keeps you going beyond all reason and for us, that is just having such personal fit with the problem we're solving and personal motivation to make this better. But as far the the actual product and what is most useful for parents and what is most useful for providers, that can't be based on our own needs, we know that. We are good product people and we understand that stuff has to be instrumented and it's almost never the thing that you expect, and you have to do user research, and you have to really go deep in understanding the data that's being presented to you.

Sara Mauskopf: I mean, I'll just give you one example, we have this amazing flow for providers to claim their page. And we started expanding it and the claim rate went way down. So I just picked up the phone and started calling some providers that were not getting through the flow, and realized they don't speak English. And so they just didn't, they were opening the email and not understanding what it said. And so it was just obvious stuff like that, that you have to go deep and be a product person. You can't just base it on your own experience of like, "This email seems pretty great, I don't understand why people wouldn't click on it," and you have to kind of go a level deeper, look at the data, look at what users are telling you, talk to users, and so we are, we don't just build for ourselves. I think the overarching thing is we care a lot about this space and this market beyond any profits that we may generate as a result of being successful. It's deeper than that.

Christian Beck: Looking back at the last few years, I feel like I've heard you say quite a few times that we thought something would happen, but it turns out that it didn't happen. So I'm curious of looking at some of the shifts or maybe many surprises, what's the one thing that surprised you the most about what Winnie's become today versus what you thought it might be four years ago?

Sara Mauskopf: I guess something that surprised me is we were directionally pretty correct. We believed in the power of crowdsourcing and building a platform that could get information at scale that did not exist on the internet already. And a lot of that came from my co-founders experience building Quora, and really understanding that there was this information in the case of Quora, like kind of existing in people's minds who were experts in these areas, and then Quora was just the product and the platform that got people to put that information on the internet for the first time. And so we believed there was something for parenting, and actually a lot of things for parenting that were like this, where information was just kind of tribal and in peoples' heads and not on the internet in a really organized, accessible way. We didn't know the exact thing yet, and that for us has turned out to be childcare.

Sara Mauskopf: But we were directionally correct. And I think that was the most surprising to me because that was just kind of a guess that we could do that, and now we have over two million users, and just growing at this like ridiculous clip, a lot thanks to organic search traffic, and it's because we have data that does not exist anywhere else on the internet.

Christian Beck: So I heard the biggest thing that surprised you was how correct you were. That's like asking somebody in a job interview, like, "What's your biggest fault?" "Oh, I work too hard." I'm kidding, I'm giving you a hard time.

Sara Mauskopf: Well, mostly because it wasn't me, it was Anne, my co-founder who was like, "This will work." I was like, "I don't know." We just have to figure out the things people are searching for, and I did doubt her, a lot of our investors and non-investors doubted her, and she was right, so I got to give her credit where credit's due.

Christian Beck: I totally understand what you're saying. I think you always, people are always trying to do the blank for blank, so it's going to be like, the Quora for parenting, and it's an easy way to kind of understand it, and then you just start thinking, "Well, is this really going to work?" But, so I, there's a lot of leaps of faith it sounds like that worked out well for you.

Sara Mauskopf: And the thing about especially data and search traffic, is it takes a long time. And so there was a period of years where we were not ranking in Google search, and just not seeing any gains in just a long time, where I was like, "Eh, I knew this wouldn't work." And she was like, "Just wait! Just wait! It takes time." And she was right, it took some time, but here we are.

Christian Beck: During that time period where you know the thing that you're going to ultimately need to grow, this is going to take time, what did you focus on? And what sort of gave you the confidence in your product in that sort of time frame?

Sara Mauskopf: I didn't have a lot of confidence in what the product was. I had product in us as product people to figure out what would be super valuable and confidence in our product process that even if we had a leaky funnel in this aspect today, we could make that work tomorrow. We could figure out how to make it better, and I just knew from my experience building products at all these tech companies, if you have a solid process and a solid team, than you just need time to figure it out. And that's where my job as CEO and keeping money in the bank became really important, and building a company where we could work on this for a long time so we have a very sustainable culture that's family friendly, and great parental leave and all these things that you would desire in a tech company, but don't actually exist until you build it yourself. So I kind of treated the company like building a product, and making sure that I was doing things in a way that would allow me to work on this for a long time. Because I did have faith in our ability to get there if we didn't run out of money and we could continue to sustain this mentally.

Anna Eaglin: I just have one final question for you. What does better product mean to you?

Sara Mauskopf: Oh, gosh. I would take it to mean this kind of cycle of improvement and iteration. I am a big believer that there's not always just a silver bullet or one right answer to having product market fit. It's a lot of iteration and work to continue to make things better and understand your users and understand what you're building and the market you're building for. So I would kind of look at it like an ever-moving scale towards making a product better.

Christian Beck: It was very exciting to get to talk to Sara Mauskopf about a parenting app, having... Well, I am still a parent, not having been a parent.

Anna Eaglin: Wow.

Christian Beck: I have been a parent and I'm also currently a parent.

Anna Eaglin: You're not just a member, you're also the founder.

Christian Beck: I'm also the founder of parenting.

Anna Eaglin: [crosstalk 00:15:15] Of your family, okay. Cool.

Christian Beck: [crosstalk 00:15:16] Oh, my family.

Anna Eaglin: Yeah.

Christian Beck: Co-founder, actually.

Anna Eaglin: Mm-hmm (affirmative). Sure.

Christian Beck: It takes two, Anna. So getting back to...

Anna Eaglin: Thanks for mansplaining.

Christian Beck: It takes two to found a family.

Christian Beck: So that... It's fun to get to talk to somebody who's founded a product that's on the consumer side and sort of, I don't know if I would really call it lifestyle, parenting isn't necessarily a lifestyle, but it's something that's outside the office space. Number one, I think the thing that stood out to us, and we should dive into right away is her whole comment about what Winnie started out as, and then how they sort of pivoted to focus on one thing.

Anna Eaglin: It's a really different approach than we've seen from other startups, that came in and they kind of had a wide variety of features. What are your thoughts about that?

Christian Beck: The first thought I have is the recurring theme that you and I have seen on this show about the founder that is solving a problem for themselves. And that's where she started. And we heard it just last week with Peter [Omble 00:16:15] with Sketch, and we heard it in Season One quite a bit. Actually no, Season Two. John Gilman, with Clear Software also talked about that. And we've talked about it from different lenses, and in fact last week with Sketch, we've talked about how they just sort of stayed in the community and just kept building based on the community. Sara found out something different, which was that the big vision that they had sort of got boiled down to one thing that was working really well. Of all those things that they had, childcare was the one thing that parents, that seemed like the biggest pain that they found with parents. And so they, I don't know if you... I guess you would call it a pivot? But they already had it, so it wasn't-

Anna Eaglin: [crosstalk 00:16:54] Kind of a focus.

Christian Beck: Yeah, it was like a focus. It's like they, and they didn't actually, that's the thing that was probably the most interesting is they didn't cut out all the other stuff. They really just whittled down the focus to something core, and then made that the emphasis of the site.

Anna Eaglin: Yeah, when we talked with Peter, he was very, they were solving their own problem. They had a vision for Sketch. And there's been some user involvement of course, we talk about how they're very integrated into the community, but Sara on the other hand, I mean, obviously she was solving her own problems because of the challenges she was facing as a new parent. But it sounds like very quickly, they went to the data and they went to see where people are finding value, so it's like, the initial genesis came from both her and Anne's wanting to solve these big problems. And I think that's because of their product background. I think she talked a lot about that. They both had product roles in other companies, and so they got very focused to see where were people finding value? Where were there happiest customers, and decided to just focus on them, but I agree. It's fascinating that they kept all that other content around, as a way to kind of bring people in to get them to the childcare, which is really where Winnie excels.

Christian Beck: Yeah, it's like they pushed those aside and made them sort of the added reason that you stay around. I think she said something like, "Come for the content, stay for the childcare utility, and then you come back for the community." And the community is derived by those extra features that used to be the focal point but didn't go away. It reminds me a little bit about how Instagram started out as Burbn, which was a FourSquare type app at first, and then they found out the things people liked the most was taking photos, so then they just honed it down to that and then they changed their brand completely, but Sara and them, they kept the Winnie brand, which was good. She had good comments on why they kept that brand, it just sort of still, that's why I don't feel like it's a pivot. Everything still felt in line with what they were trying to do, it was just a more refined focus.

Anna Eaglin: Yeah, having the content too seems like a great lead gen into the product. So she talked a bit about how you're having issues potty training, and you search, you find a forum conversation in Winnie about potty training. You get there, you learn more about it. And then you kind of become part of the community, you find that value. Again, you're in through content, you join Winnie, you might use the childcare, but you're always coming back because of the content. It's like the content is both the entry and the small circle, the small loop that keeps you coming back, which is so fascinating to be kind of, it's like, I don't know. A double-sided funnel? I don't know what the marketing metaphor is for that.

Christian Beck: [crosstalk 00:19:19] A two? Wow, yeah.

Christian Beck: Well, and she had that insight too. I also want to touch on the other thing you just brought up. Well, there's a team of attacking a problem space that's seemingly infinite, but then she started talking about how a lot of the stuff that they wanted to do was going to take time to bear out. And so she talked about initially when they sort of made that pivot, they had to stay the course and that's probably a little bit of an anxiety-ridden moment, but what stood out with you about that aspect of Sara growing Winnie when they pivoted?

Anna Eaglin: Yeah, I mean, what I really thought about in that part is it must have been really hard for them just to wait, you know? Again, they felt like they were doing everything right. They had all the content out, and they just, it was just waiting for that. For them to move up in those search rankings, and I do find it very interesting that they, like she said, they trusted their product process. And I think that's, that's got to be hard to sit there and wait and to wait to see those numbers, and really not shift anymore variables.

Christian Beck: Yeah, it's like, I don't think that process alone makes good product, but, and so I think it's not that we're saying that, it seems like with Sara and her co-founder with Winnie, they had a good product, it's just that it was going to take time for it to stick based off of the business model that they had, which was the content going up in search rankings. So if you have something good, then a strong process, and both of them having amazing stellar product resumes were very, very confident and had faith in their process, with their product and the way that they were handling feedback and tweaks that eventually, with a good product and the right process, the results would start to come, and it seems to have happened over time.

Anna Eaglin: My big question would be, how do you know when you need to just pump the brakes and just wait, and see the fruits of your labor, or when is it time to change what you're doing?

Christian Beck: I don't know if that's a hypothetical question, or one that we are going to answer, because it's a really good question.

Anna Eaglin: [crosstalk 00:21:09] It is a good question.

Christian Beck: I think with them, for one having the experience and having a really strong foundation for product, which we try to give on this show when we talk to people like Jeremy Leventhal with Springbuck in Season One, or Rod Foyer, a lot of these experienced product professionals talk about principles and the guiding philosophy. And so I think for those of you listening and wanting an answer to Anna's question, I think it really starts with being confident and having a methodology for how you're going to handle products, so that when you want to make these sort of risky decisions, you at least know that you don't need to keep jerking around from week to week, changing course. Sometimes it just might take time.

Anna Eaglin: Thanks so much for listening to the show this week. If you haven't yet, be sure to subscribe, rate, and review this podcast. Until then, visit, and subscribe to learn how you can take your product to the next level. As always, we're curious, what does better product mean to you? Hit us up on Twitter @InnovateMap, or shoot us an email at

Christian Beck: I'm Christian.

Anna Eaglin: And I'm Anna, and you've been listening to Better Product.

Christian Beck: [crosstalk 00:22:15] Better Product.

Anna Eaglin: Drop mic!

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