8/50 Personalities: Sara Mauskopf – CEO & Co-founder of Winnie, Childcare Advocate & Product Visionary

 

Introduction

In the eighth installment of our 50 Personalities Series, we introduce Sara Mauskopf, the CEO and co-founder of Winnie, a groundbreaking childcare marketplace that connects parents to over 200,000 licensed daycare and preschool providers across the United States. As a former product leader at major tech companies like Twitter, YouTube, and Google, Sara’s career has been marked by a unique combination of tech innovation and a personal mission to improve the lives of families. Through Winnie, Sara has turned her vision of better access to affordable, quality childcare into a reality, reshaping the landscape of early childhood education.

Background & Bio

Sara Mauskopf’s journey into the world of entrepreneurship and tech leadership began in the fast-paced world of Silicon Valley. Before founding Winnie, Sara held product leadership roles at some of the biggest names in tech—Twitter, YouTube, Postmates, and Google. She honed her skills at the intersection of technology, user experience, and business strategy, but it was her experience as a parent that drove her to create Winnie, a company focused on solving one of the most pressing challenges parents face: finding quality childcare.

Sara is based in San Francisco, where she lives with her husband and three children. Her personal experiences as a working parent and the challenges she faced in finding reliable, affordable childcare deeply informed the mission of Winnie, a company she founded with the goal of making childcare easier to access and more affordable for parents across the country.

Mission & Vision

Winnie began as a vague idea centered around helping parents and making their lives easier. Through the process of building the company, Sara and her team zeroed in on one of the most life-changing problems for working parents: finding quality childcare. In the United States, where much of early childhood education is privately provided rather than publicly funded, navigating the childcare system can be a daunting and confusing task for parents.

The solution that Winnie offers is simple yet transformative: an online platform that allows parents to search for and discover childcare providers, including daycares and preschools, many of which are hidden from traditional online searches. Sara’s vision was to create a marketplace that connects parents with licensed childcare providers, ensuring that more families have access to high-quality early education.

One of the key insights that shaped Winnie was the realization that over half of licensed daycare and preschool providers in the U.S. were not online at all. Many of these providers operate out of their homes, which makes them difficult to find through traditional search methods. By creating a platform that enables parents to discover these hidden gems, Sara and her team have opened up more options for parents, making childcare more accessible and affordable.

Industry Impact & Challenges

The childcare industry in the U.S. has long been plagued by a lack of visibility and a fragmented marketplace. Families often struggle to find quality options that fit their schedules and budgets. Many parents are unaware of the wide range of childcare options available to them, especially those that are run out of home-based settings. This issue is particularly acute for working parents who need reliable and consistent childcare in order to balance their careers and family life.

Through Winnie, Sara Mauskopf has made a significant impact on this industry by addressing both the supply and demand sides of the childcare market. She has created a platform where parents can easily browse, compare, and choose from a vast array of childcare providers that they otherwise may have never discovered. This service empowers parents to make informed decisions about their children's early education, ultimately enabling them to return to work with peace of mind that their children are receiving quality care.

Beyond the platform, Winnie also plays a key role in advocating for policy changes that support working families, such as providing childcare benefits through employer partnerships and collaborating with government entities to improve access to affordable childcare nationwide.

Leadership & Entrepreneurial Journey

Sara Mauskopf's entrepreneurial journey has not been without its challenges, particularly when it comes to fundraising and navigating Silicon Valley's gender biases. Like many women founders, Sara faced unique hurdles when seeking investment for her vision. She’s spoken candidly about the difference in how male and female entrepreneurs are questioned by investors, with women often asked about their ability to balance work and family life or about their personal “track record” in ways that their male counterparts are not.

Despite these challenges, Sara's perseverance and strong vision for Winnie have allowed her to secure the funding and resources needed to grow her company into the largest childcare marketplace in the U.S. In 2023, Winnie raised a $12 million Series A round, further cementing its position as a leader in the childcare space.

Career Highlights

• CEO & Co-founder of Winnie: Sara’s most notable achievement is her leadership at Winnie, which connects parents to over 200,000 licensed daycare and preschool providers across the country. Under her guidance, the company has grown rapidly and has been instrumental in improving access to childcare for families nationwide.

• Product Leadership at Twitter, YouTube, Google, and Postmates: Prior to founding Winnie, Sara held product leadership roles at major tech companies, including Twitter, YouTube, Postmates, and Google. Her expertise in building user-centered products and navigating the fast-paced tech environment has been a key factor in the success of Winnie.

• $12 Million Series A Funding: In 2023, Winnie secured $12 million in Series A funding, which has helped fuel its expansion and solidify its position as a trusted resource for parents seeking childcare options.

Challenges Faced by Women Entrepreneurs

Sara Mauskopf has openly discussed the unique challenges faced by women entrepreneurs, especially in fundraising. Women often face different questions from investors, who may inquire about their ability to balance family and work life or question their track record differently than male founders. This disparity highlights the gender biases that still exist in venture capital and entrepreneurship. Despite these challenges, Sara has continued to push forward, ensuring that Winnie continues to grow and meet the needs of working parents.

Future of Winnie

Looking ahead, Sara Mauskopf is focused on scaling Winnie and making childcare more accessible for families everywhere. She aims to expand the platform’s reach, increase the number of providers on the marketplace, and continue advocating for childcare benefits that support working parents. In the coming years, Sara plans to grow Winnie into an even more essential resource for parents, empowering them to find high-quality, affordable childcare that fits their needs and schedules.

Sara’s long-term vision for Winnie is to continue reshaping the childcare industry by providing a one-stop solution for families to find care, ensuring that every parent has access to the resources they need to thrive both personally and professionally.

Sara Mauskopf is an inspiring entrepreneur and visionary who is changing the landscape of early childhood education and childcare accessibility. By founding Winnie, she has created a platform that helps parents navigate one of the most challenging aspects of family life: finding quality childcare. Sara’s leadership, combined with her personal commitment to improving the lives of families, makes her a powerful advocate for working parents and an influential figure in the world of tech entrepreneurship.