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Hi, I'm Sara Mauskopf, the CEO and co-founder of Winnie. Winnie is a free app for AndroidiOS and the web that's like Google Maps plus Yelp plus a parenting group, all combined in one. Winnie can point you to the nearest changing table, daycare with opening spaces right now, and even restaurants where kids eat free. And the community is amazing too. It's a genuinely great free resource for anyone who cares for children. We now have half a million users across the United States and we've written about how we grew our initial user base here.

My background is in consumer technology and product management. Prior to founding Winnie I was the Director of Product at Postmates. Before that I was an early employee and Product Manager at Twitter and prior to that spent a few years at YouTube and Google. I graduated with a Computer Science and Engineering degree from MIT. 

I live with my husband, daughter (and another daughter on the way) in San Francisco. Ask me about startups, parenting, building and growing consumer products, or whatever is on your mind.


You can follow Sara and her company Winnie on Twitter: @sm and @winnie

She will be live on Feb 8 starting at 930 AM PT for one and a half hoursduring which she will answer as many questions as possible.

  • PH

    Pradyut Hande

    about 2 years ago #

    Hey, Sara. Glad to have you here!

    For an app like Winnie, how do you go about increasing user retention in the long-run?

    • SM

      Sara Mauskopf

      about 2 years ago #

      Some people think the best and only way to get a user coming back over time to your product is to gamify the product and use addictive hacks like frequent push notifications. A timely example of this is the HQ Trivia app which has had massive growth recently. Their product is gamified (it’s literally a game) and they push notify you twice a day to tell you to come in and play trivia. For some products, this approach works, as HQ Trivia illustrates, but it’s not the only way to increase user retention and the pitfall of tactics like this is they may not hold up over time. Users can burn out just as fast as they fall in love. There are other levers to use that may be better suited to your product.

      My favorite retention lever is utility. How does Google Maps keep me coming back over time? Well, at least weekly I am driving somewhere new and I need directions so I open the app. And on a daily basis I open Google Maps to figure out how much traffic there is on my commute so I make sure to leave work in time to get my daughter. Google Maps doesn’t need to remind me to come back and use it by sending me lots of push notifications and it doesn’t need to provide extra rewards or incentives. The reward is the information I get. It makes my life easier so I continue to use it. It’s as simple as that.

      At Winnie, we provide a utility that keeps parents coming back over time when they are seeking new information. There’s a ton of information you need over the course of raising kids and just when you think you’ve figured something out, your kids enter a new stage and you have new questions. Figured out breastfeeding? Now it’s time to introduce solids. Figured out your favorite restaurant where you can fit a stroller at the table? Well now your kid is sitting up so you need a restaurant with high chairs. By being a tool that provides people with all kinds of parenting information over the lifetime of raising children we take advantage of these naturally occurring reactivation points where parents need new information. We don’t have to invent some kind of new thing for people to do and convince them to do it every day. We literally just provide an easier way to get the information they’re already looking for.

      That said, you also can’t just build an amazing product and expect people to always remember come to you. It’s also really important we meet people where they are and remind them of the value Winnie provides. People are busy and parents are an extreme example of this. At Winnie we send a weekly personalized digest email summarizing our most interesting parenting discussions for you. This deep links back into the app and has helped retain and reactivate users.

      4 Share
  • TB

    Tristan Bailey

    about 2 years ago #

    Where do you look to for advice and personal growth as a founder? (Do you work with a mentor or similar)

    • SM

      Sara Mauskopf

      about 2 years ago #

      This is a great question because it’s really hard when you have no boss to get feedback and improve your performance. In one sense your performance is just the company’s performance but the company’s performance isn’t just how you’re doing in the market, it’s how you’re doing internally with employees. Are your employees happy? Are they being treated fairly? Do they have a sense of purpose? Are they excited to come to work each day? Do they feel like their work is helping them develop and grow? It’s harder to keep a pulse on this. There’s no dashboard for it.

      As a founder, you need to actively seek out feedback in a more aggressive way than you would if you worked for a big company. You need to ask for feedback any chance you get. I ask my cofounder, my employees, my investors, and even random people I interact with. You won’t always get honest feedback (for example, your employees may not always be honest with you when something is bothering them) so you have to be more aggressive about digging for this.

      I also connect with other founders and former founders and don’t hesitate to talk through problems with them. I’d consider all these people my mentors even when they are peers or not even as far along in their journeys as I am. Sometimes having the view of someone removed from the day to day workings of your company can be really helpful. It’s been surprising to me how many of the problems we’ve faced as a fast-growing startup are not all that unique so talking it through with someone who has been there can help provide faster solutions than trying to figure it all out from scratch.

      Finally, I’ll mention that one day I’d love to hire an executive coach. I think taking time for personal development as a founder is really important.

      3 Share
  • JP

    John Phamvan

    about 2 years ago #

    Hi Sara

    a. What tools are you using at Winnie for experimentation & analytics right now?
    Have you added any tool(s) to the stack recently? If yes, why?

    b. Where does your data live, ie what is the "source of truth"?

    c. What collaboration tools does the team use ?

    Thanks!
    John

    • SM

      Sara Mauskopf

      about 2 years ago #

      We primarily use Mixpanel and Google Analytics for our analytics but there are a bunch of metrics we need to track ourselves that we don’t track through those tools, mostly relating to how much data we have on the platform. We have over 1M places with proprietary data and we track that information on our end. So depending on the data we’re looking at, the source of truth might be our own dashboards or it might be in a third party tool.

      As far as experimentation, we track this on an adhoc basis. We don’t have a sophisticated platform yet for experimentation so when we want to run an experiment we build it, log the things we think are important and analyze those metrics after we’ve collected enough data to make a decision.

      The primary collaboration tool we use is Slack. One of our employees is remote so we try to communicate all important stuff through Slack so he doesn’t miss anything. We also use Google Docs and Asana on a daily basis.

  • TB

    Tristan Bailey

    about 2 years ago #

    Do you have to implement more security or background checking for recommendations provuded, as they cover children?

    • SM

      Sara Mauskopf

      about 2 years ago #

      The founding team at Winnie comes from companies including Twitter, Quora, YouTube, and Reddit so we know all too well all the issues and pitfalls that can come with user-generated content. It was super important to us to make sure that information you find on Winnie is really high quality and valuable and that our community is safe. We focused on this from the very beginning because once your platform achieves scale, it’s hard to slap this on as an afterthought. There are a few big things we do to ensure safety.

      First and most importantly, every piece of content is moderated to ensure the information stays high quality, relevant, and safe. This also helps ensure that discussions and conversations don’t become toxic or devolve into something that isn’t helpful. We also use a lot of signals similar to a system like Quora to make sure the best content is what is getting shown to users and the low quality content is not.

      Related to the first point, we built tools to help us moderate content at scale so even when we get a big influx of users and content we are able to keep on top of anything questionable. These tools include user inputs like flagging and reporting that we know when something needs our attention immediately.

      Finally, we built user-facing features that enable users can control how much they share. For example you can post questions and comment anonymously. This helps people ask questions they may otherwise be afraid to ask and share authentic answers without having to worry about always showing the Instagram-worthy version of themselves! You can also mask the faces of any photos you post with cute stickers and our “mask faces” button.

      2 Share
      • AA

        Anuj Adhiya

        about 2 years ago #

        Can relate to the "ask questions anonymously" piece. We saw an uptick in questions asked once this was introduced as well.
        Some were afraid to ask Qs that their employers might see (if it was about getting hired) or ones that might seem too "basic or "stupid", especially when they had a pubic reputation about a certain level of knowledge.

  • AL

    Arsene Lavaux

    about 2 years ago #

    Bonjour Sara- Intrigued by your science background and how it helped you grow your entrepreneurial aspirations.

    In Europe, when you study engineering, you learn very theoretical, and cool, math and physics concepts.
    Only a few in my experience apply to growth discovery and scalability in real-life growth marketing.

    Do you have a different experience with how much of your math ability is put to work when growing a business?

    Which mathematical concepts have you found most useful to deliver growth results so far?

    Thanks for the learning!

  • GH

    Glen Harper

    about 2 years ago #

    Thank you for joining us today, Sara.

    I read the post on growing your user base - that was a great read.
    Anuj did ask a Q about it when the post showed up on the community a few weeks back, which I would love to hear more about.
    Pasting it here for your convenience:

    "Would love to know more about how Apple featured Winnie on the front page of the App Store. Was that because of some specific initiative/knowing someone on the team etc or whether that was something that happened because they'd followed all the guidelines and randomly got picked because of that. "

    • SM

      Sara Mauskopf

      about 2 years ago #

      First and foremost, we built a native iOS app and we work hard to keep it up to date with the latest and greatest UI guidelines and technology from Apple. This is essentially a requirement to be featured. We also strive to have a really beautiful and unique design. Our brand is really important to us and we’ve focused on establishing that brand from the beginning. Apple definitely likes to feature apps that have beautiful assets and app icons.

      We also have contacts on the App Store team that we keep in touch with. We let them know about major updates in advance. It’s a way to keep them updated on what makes our app interesting so if they are putting together a collection or feature, they can remember to include us if it makes sense.

      The final thing I’ll mention on this is it’s probably the wrong thing to focus on. We’ve been featured twice and we’ve found that these users are more “churny” than normal users who discover us through our content or through word of mouth. These people are maybe not even parents/caregivers so there’s not even a reason why they would use Winnie. We prefer to spend our time focusing on building a great product and building out our organic growth engine (we get the majority of our growth through the content on Winnie) as this gets us in front of our target audience and these users retain better over time.

      2 Share
  • DH

    Dani Hart

    about 2 years ago #

    Hey Sara - so excited to have you here today!

    I can see how you can use friends and family to get them excited about something like Winnie to get your first users.

    a. I suspect you encountered many friends/family where Winnie was not a must-have but a nice to have.
    So what traits/usage metrics were you able to hone in on that gave you an indication that these early users would likely be long term users as well?

    b. Assume Winnie was some sort of super-techy enterprise database marketplace type product (why not eh?) - something that most friends and family would have no interest in. How would you have gone about getting your first 10-100 users in that case when the "easy" friends and family route to seed initial users wouldn't have been available to you?

    • SM

      Sara Mauskopf

      about 2 years ago #

      With Winnie it was somewhat straightforward to understand early whether we were on to something useful because we saw that the users who got the information they were looking for and the answers to their questions were more likely to retain long term. The users who downloaded Winnie and couldn’t find what they were looking for didn’t come back. This was especially obvious early on when we had great data in some regions and very poor data in others. This helped us hone in on the importance of solving the “cold start” problem and getting great national data so we spent a long time building out the tools and systems for doing data collection at scale. We wanted to make sure even a user in a small town in Kentucky could download Winnie and find great family-friendly places in their area.

      Getting the first 10-100 users when you don’t have a friends and family route is probably harder but better. Even if you have to buy those first 100 users through ads, you’re probably going to get more reliable feedback that is more representative of what you actually need to build to attract real customers. Although we did start with a friends and family beta at Winnie, we quickly realized we needed to open the product up and collect feedback from users across the country. Our friends in San Francisco are not representative of the majority of the parenting market so it was extremely critical we did not build a product that just worked for them.

      2 Share
  • TN

    Tri Nguyen

    about 2 years ago #

    Hey Sara,

    What is Winnie's "wow moment"?
    Is that wow moment different for moms vs dads?
    How have you optimized for getting people to this must-have experience as soon as possible?
    Any tests and results that you can share around this?

  • MD

    Mark Anthony de Jesus

    about 2 years ago #

    In the post you shared it says that many of your early growth initiatives were actually data acquisition projects
    Can you talk more about the timing of these projects vis a vis getting early users (ie before/during?) and how you prioritized these activities against early acquisition/activation/retention type needs?

    Also, I'd love to hear more about the technologies and sources used within these projects.
    Lastly, would there have been any way to source (any of) this data without someone technical on the team? If yes, how?

    • SM

      Sara Mauskopf

      about 2 years ago #

      Early on we focused a lot of acquiring the data our users were looking for, stuff like restaurants where kids eat free, playgrounds, libraries with kids story times, and places to nurse or change a diaper. We had to source this data from a bunch of places, derive it ourselves, and build systems to contact businesses at scale to get this information. This was all proprietary technology we built in-house.

      We also crowdsource data from our users so as we bring more users onto the platform we collect more data. Even if these early users didn’t retain super well, they created the data that would retain the next users who signed up. Therefore, we didn’t focus on retention early on because we knew that the better our data was the more likely our users were to retain.

      As far as whether this would have been possible without a technical team, we feel strongly that the answer is no. Many people have attempted this problem and not been able to achieve any level of scale because they didn’t approach the problem from a tech standpoint. They have built local blogs or point solutions. My cofounder Anne and I knew that our backgrounds working at some of the best technology companies with some of the best engineers gave us a really unique competitive advantage in tackling the parenting space, a space that has been starved of technology and great engineering.

  • JF

    Javier Feldman

    about 2 years ago #

    Hola, Sara

    Can you talk about how you honed in on when - and why - existing users will share the link to Winnie to bring in new users?
    What motivations and incentives were you able to latch on to?

  • SM

    Sara Mauskopf

    about 2 years ago #

    Thanks so much everyone! The live portion of this AMA is over but I'll try to sign back on later and answer some more questions!

  • AW

    alex weinbaum

    about 2 years ago #

    Very inspiring Sara! If you could go back in time, what is one piece of advice you wish you heard before you became an entrepreneur?

  • AA

    Anuj Adhiya

    about 2 years ago #

    Hey Sara - so cool to finally have you on!

    There is no shortage of parental help groups on meetup.com or on FB (or even on Whatsapp). There's even sites that make you begin your parenting journey before your kid is even born like Circle of Moms that aim to retain users before and after the kid is born as well.

    So what is it about Winnie that makes parents migrate away from existing resources and/or choose Winnie over sites they are already familiar with?

    What lessons have you learned about how and when to appeal to potential Winnie users so that they see its value over other existing sites?

    • SM

      Sara Mauskopf

      about 2 years ago #

      Parents come to Winnie because we have information you can’t get anywhere else, at least not easily. People use Winnie to find preschools with open spaces. They use Winnie when they’re on the go and are looking for a changing table or a place to nurse. They use Winnie when they’re traveling somewhere new and want to find a restaurant with a kids menu and play area, or where kids eat free. They use Winnie when they have questions or need information and want to be connected to other people who can help, whether it’s someone who lives nearby or a has a similar aged child or shares the same interests.

      When I became a parent, I was shocked to find that all this information wasn’t at my fingertips. The status quo, like you pointed out, is old school web forums that existed back when the internet was mostly something you accessed on your computer at home, like Circle of Moms or BabyCenter that has been around since I was a child! Or, as you also pointed out, you have to network and meet up with other parents and join private groups to find something as fundamental as childcare. It takes a lot of time that frankly we don’t have as millennials. This is the first generation where the majority of households don’t have a stay at home parent. We’re also the mobile first generation that is used to everything being a swipe and a tap away. There is no one who's full time job it is to figure out this stuff so we need tools to fill the gap.

      So, we don’t do a lot of work trying to appeal to users to use us over other products since there’s really nothing else out there that solves parents’ problems the way Winnie does. The majority of our efforts are about increasing awareness of Winnie and how you can use it.

      2 Share
  • DO

    Danielle Olivas

    about 2 years ago #

    Hey Sara!
    I think the "How Does She Do It"? moniker applies to you for sure!
    How are you managing being the CEO of a growing startup with a family and a kid on the way (Congrats btw!)?
    Any lessons those among us - even those not in your situation - can learn about managing priorities and just not going crazy in general? Most importantly, how do you just switch off and not get drawn back into something or the other to do with the business - given it to is your baby ?

    • SM

      Sara Mauskopf

      about 2 years ago #

      For me, being a parent is my superpower. Because I have limited hours in the office (I have to be home at 7pm to take care of my daughter) I more intensely focus when I’m working and get more done. Before I was a mom, it was easy for me to get distracted or waste time during the work day and I would end up working longer hours but getting far less done.

      The same thing goes for when I’m spending time with my family. I try to focus on them and their needs and not get distracted by work. I’ve found having this separation is nice because it gives me a built-in break from each which is much needed in both the case of raising young kids and building a startup. I’m absolutely certain in my case I’m a better, more patient mom with my daughter because I get a break from her.

      One thing that helps me context switch and focus on either work or family is that I’ve come to terms with the fact that I can’t be perfect. I’d love to be the perfect mom and pack my daughter a healthy lunch for preschool, for example, but the lunch they serve at preschool is probably not going to kill her and I can serve my daughter healthy food for all her other meals. This is a small thing but being forgiving and not having to do things perfectly all the time gives me the time and space I need to have both a successful business and raise kids.

      2 Share
      • AA

        Anuj Adhiya

        about 2 years ago #

        I think the big about coming to terms with not being able to be the perfect parent all the time doesn't get as much ink as it should. Thanks for the honest response.

  • JD

    James Dunn

    about 2 years ago #

    Hi Sara,
    What is Winnie's biggest growth challenge right now and how are you tackling it?

  • SK

    S Kodial

    about 2 years ago #

    Hi Sara
    Other than what you've already shared so far, can you talk about an experiment (at Winnie or elsewhere) that was either a big win or led to some insight you didn't have before?

  • PD

    Porus Daruvala

    about 2 years ago #

    Thanks for your time here, Sara.

    1. I see that you'll recently announced partnerships with a few other companies.
    How did those come about? Did you approach them or vice versa?
    What lessons have you learned so far about what make for successful, long term alliances. Would love to hear any war stories as well.

    And a related q:

    2. Assume that a very early, MVP stage startup (ie you are the bigger fish) approached you with an idea to partner up in some way. What would they have do/show you for you to be able to at least dip your toe into that pond and test it out?

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