From Searching to Solving: How Winnie Is Transforming Childcare for Parents and Providers

In this Capital Class episode, Strategos Partner and host Adam Giery sits down with Sara Mauskopf, co-founder and CEO of Winnie, the national platform millions of parents use to discover and evaluate licensed child care. A mom of three and a vocal advocate for high-quality early education, Sara traces Winnie’s “messy first draft” from a local activity finder to a nationwide, two-sided marketplace built on trust, licensing data, and parent reviews. Sara explains how the early-education landscape has transformed over the past decade: investor interest has grown, providers have adopted more technology, and cultural norms have shifted from “daycare as a dirty word” to early learning as a valued—often expected—step before kindergarten. She argues candidly that child care should be expensive because it’s profoundly valuable, but families shouldn’t shoulder the cost alone—public funding and employers must help close the gap. From the provider’s side, she demystifies tight margins, regulations, and what it takes to run a sustainable, recession-resilient business. Digging into Winnie’s growth, Sara recounts the moment product-market fit clicked, why the team chose a national footprint early, how providers themselves pushed Winnie toward monetization, and what surviving shocks like the SVB crisis taught them about resilience and profitability. Tune in for valuable insights on innovation, leadership, and where the future of family tech is headed. Key Moments 04:48 Evolving Perceptions of Childcare 07:20 Challenges Faced by Childcare Providers 12:10 Licensed Childcare Marketplace 14:35 Unexpected Childcare Marketplace Journey 17:02 Winnie's Shift to Childcare Marketplace 20:26 Monetization Dilemma for Childcare Marketplace 24:05 Event Led to Financial Strategy Shift 27:17 Profitability Over Fundraising 31:41 Oversharing and Open Book Life 35:19 Winnie Expands to K12 Education 38:25 "Growth: In-Person Customer Interaction" Connect with Sara Mauskopf LinkedIn: Website: ============================= Learn more about Strategos Group: LinkedIn: 🚨

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From Searching to Solving: How Winnie Is Transforming Childcare for Parents and Providers is an episode from Capital Class by Adam Giery.

This episode is 59:37 long.

This episode was published on Sep 23, 2025.

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