Portrait No. 001
Sara Mauskopf
Co-Founder & CEO
Winnie
I started Winnie after becoming a mother and experiencing firsthand how challenging it is to find childcare, and how that keeps women from staying in the workforce. I was shocked that something so foundational to families’ lives and the economy operated with so little transparency and so much friction. As a tech and product person, I kept thinking: this is a solvable problem. Parents deserved better information, and providers deserved modern tools to be discovered and trusted. Winnie is now the leading marketplace for child care and education in the United States, used by millions of families across all 50 states. We help parents find, evaluate, and enroll in child care, preschool, after-school programs, camps, and K–12 schools.
Chapter I
The toughest challenges you've faced as a founder.
Building Winnie has been a challenging 10 year journey. Child care is one of the hardest markets in America: deeply fragmented, offline, underfunded and undervalued. We also operate in an industry where outcomes matter enormously. As a woman and a mother, I faced skepticism early on that male founders rarely encounter. I was often asked if I was building a lifestyle business, whether I would stay committed through having kids, or if the market was big enough. Fundraising while pregnant and parenting young children was also a challenge. We survived a cancer diagnosis, multiple market cycles, policy whiplash, and the shock of COVID. Through it all, we kept building. Today, Winnie serves millions of families across all 50 states, has raised tens of millions in venture funding, and has become the most comprehensive marketplace for child care and early education in the U.S.
Chapter II
Your vision.
As AI replaces every industry, people will still want/need human childcare providers. Winnie is even more valuable/critical in a world where people rely on AI for everything because they will still need Winnie to be that interface between the child care providers (humans in the real world) and the internet/AI. Winnie has the deep, proprietary data set of 500k child care businesses across the United States and the relationships with the child care providers so that parents can get spots in their child care. We can provide the interface for agents to book tours/spots in daycares like we do for humans, but the providers will also need us as their interface between those agents and their business.
Chapter III
The impact you want to leave behind — for your industry, your community, and the women who come next.
I hope my legacy is that women can find childcare and don't need to drop out of the workforce, child care providers (predominantly women) are seen and supported, and women founders to believe that starting companies rooted in lived experience is not a liability but an advantage. If Winnie helped shift child care from a private struggle to shared infrastructure, and if a generation of women felt more empowered to build ambitious companies while raising families, that would be a great outcome.