On building community and increasing childcare accessibility: a conversation with Winnie's CEO, Sara MauskopfFeatured

I spoke with Sara Mauskopf, CEO and co-founder of Winnie, a marketplace for childcare and early education. Sara and I discussed her founding story, bootstrapping marketplace businesses, building communities, and leading Winnie through COVID-19.Prior to founding Winnie, Sara worked as director of product at Postmates. At the time, she had just had her first child and had recently come back to work after maternity leave. She quickly realized that her new life as a working mom looked quite different. Managing both work and parenting was a novel challenge, and there were hardly any technology enabled solutions to support her and other working moms. Sara shared her frustration with her coworker (who later became her co-founder) and found the problem resonated deeply with her as well. Through further researching the problem and market, Sara learned that millennials have the highest number of dual parent households. Women work more than ever but the amount of work they need to do at home remains unchanged. When families struggle with childcare, it is more often women who drop out of the workforce. So, she sought to create a solution to make parents’ lives easier. Sara identified childcare as the biggest problem to solve within the broader parenting category. Childcare is the great enabler: access to high quality, affordable child care could truly change the lives and trajectories of parents and their children. Ultimately, there is no economy without proper childcare. Thus, Sara and her co-founder, Anne Halsall created Winnie. Reflecting on her journey with Winnie, Sara shares the process of bootstrapping the initial marketplace. Specifically they aggregated all licensed daycares and preschools, collecting information of these facilities. Then, they made this data rich resource free to parents. At the time, there were few other curated, informative lists of childcare options for parents (Yelp was a far second but was sparse in their coverage and depth of information shared on each option), so parents initially came to Winnie eager to use the product. Getting providers onboard as partners was a bit more difficult because these places tended to be less technologically advanced, but ultimately, from seeing the growth in parents using the platform, providers agreed to partner too. After they reached a critical mass, Winnie could monetize from providers advertising on the platform to fill spaces. When launching Winnie, Sara and Anne launched globally for parents to start in order to get a wide variety of users from all around the world. By doing this and receiving and incorporating early user feedback, they were able to build a more broadly useful product and one not limited by their views or needs. On the provider side, the options were more localized, so the team took a similarly localized approach, starting with San Francisco (where they are based) to test the waters and then moving state by state once they finalized their offering. Aside from the listings themselves, Winnie has a vibrant community of parents asking questions and sharing advice. Parents come to the platform to identify childcare options but end up staying on the platform to engage with the community. The team at Winnie has also learned a lot about their customers’ needs through community postings (it was how they first realized childcare was the biggest need and decided to focus on it). Although it may seem that finding childcare is just one decision at a particular point in time, Sara underscores the importance of long term relationships with their users. Many times, parents reevaluate childcare options or seek different options for different children. In this way, the user generated content and organic interactions on Winnie’s community platform continue to deliver new and actionable value for parents, keeping them engaged on the platform through all their key child care decisions. In the current COVID-19 crisis, Winnie is experiencing unique challenges but finding opportunities and creative solutions. Winnie’s target demographic is parents with children aged 0-5, thereby focusing specifically on daycare and preschools. While a substantial amount of schooling at the secondary and university level have moved online to Zoom, virtual schooling certainly does not work for children this young. Moreover, even after COVID-19, some daycares and preschools may no longer be able to open, given their low margin operations with limited capital to sustain the business through these extended periods of low demand. While many parents are now homeschooling their young children, frontline healthcare workers are not able to and still need childcare options. So Winnie has stepped up to connect these essential workers with emergency childcare. On the provider side, Winnie is also connecting childcare centers with forms of relief, including financing options and helping them fill empty spots. On advice for other CEOs and leaders during COVID-19, Sara underscores the importance of being flexible. Child care challenges at home are immensely crucial and high priority, so be understanding of employees as they adjust to their new environments and schedules. On key takeaways from the challenges COVID-19 presents at home, Sara hopes that society can move forward with a greater understanding of and appreciation for teachers and childcare workers as well as the need to equally divide tasks at home.
This is a great interview! We also had the chance to talk to Sara on our podcast, Better Product, a few months back in case anyone is looking for more insights:
That’s awesome! Thank you for sharing!