Sara Mauskopf

June 2015. Sara Mauskopf - formerly of YouTube, Twitter, and Postmates - has her first child. The baby arrives; the spreadsheet follows. She wants daycare. Daycare, it turns out, does not want to be found. No central database. No reviews worth trusting. No pricing anywhere. She describes the process as absurdly broken for something that is both critical infrastructure for working parents and one of the most consequential decisions a family makes. She and Anne Halsall, who had the same problem and the same technical background, compare notes. The comparison takes about five minutes. Winnie is born in early 2016.

What makes this particular founding story interesting is not that it's a pivot-of-necessity - plenty of companies are. It's that Mauskopf approached childcare discovery as a product problem with a specific diagnosis: the information exists, it's just inaccessible, fragmented, and nobody with real engineering chops has bothered to aggregate it. Her years running product at Twitter - where she led photos and media, then the entire Discovery team doing content recommendations and personalization at scale - turned out to be exactly the training she needed to build a platform where structured data and community content combine to make 250,000+ providers findable.

The platform has expanded methodically since then. Daycare first, then preschool and early education, then school-age childcare, then summer camps and au pairs. Winnie now covers more than 7,000 U.S. cities - not just major metros. This is deliberate. Childcare deserts are a rural and suburban problem as much as an urban one, and Mauskopf has said consistently that she sees the mission as national, not just coastal.

In 2023 Winnie landed at #177 on the Inc. 5000 list of fastest-growing private companies, was named the #1 Consumer Services Company on that list, and ranked #34 among all California companies. Multimillion-dollar revenue, 54 employees, and a majority-female engineering team. The funding story runs to $15.5 million total - a $4M seed in 2018 and a $9M Series A in October 2019, the latter led by Rethink Impact, a female-led fund focused on investing in women-led companies using technology to address global challenges. Jenny Abramson of Rethink joined the board. Co-investors included Reach Capital, Unusual Ventures, April Underwood (Slack's former CPO), and Afore Capital.

Before Winnie there was YouTube, where Mauskopf led global partnerships for the Music business - at the time YouTube's largest partner business by both revenue and views - in a hybrid role that blended partnerships and engineering. Then four years at Twitter across multiple product roles: Photos and Media, the Discovery team, and twitter.com. Then a year as Director of Product at Postmates. The common thread is consumer-scale product work, which is exactly the muscle that building a two-sided childcare marketplace requires. She has also written for Fortune, Inc., and Forbes, and been a General Assembly instructor - the kind of teaching that suggests she thinks about the mechanics of her work, not just the execution.

Her Instagram bio reads: "Always influenced, never an influencer." She has three children and runs a fast-growing company. That sentence-long bio is doing more work than most founders' pitch decks.