Sarah O'Leary joined Willow Innovations as VP of Growth in 2019. Four years later she was running it. Here is how a consultant turned brand builder reframed motherhood, and then bet on merging two femtech rivals.
Sarah O'Leary did not invent the wearable breast pump. She did not found the company that built it. She walked in the door in 2019 as a vice president of growth, one hire among many at a Mountain View startup that had already made noise for putting a pump entirely inside a bra. Four years later she was the person deciding where that company went next. The climb says something about her, and something about how Willow decides who leads it.
Her path to femtech was not a straight line. O'Leary started in consulting, working with private-equity clients, the kind of work that trains you to take apart a business and find the number that actually matters. After an MBA she moved into sales and business development at a skincare company that had once been a consulting client. Then came Tea Collection, a children's fashion brand, where she ran marketing, strategy and sales. That job, she has said, is where she found what she was good at: building brands that people feel something about.
Consulting, skincare, kids' clothing, breast pumps. On a resume it reads like someone who never settled. Read it the other way and every stop taught the same lesson: figure out who actually uses the thing, and build everything around that person. At Willow, that person is a new mother, and O'Leary has spent years arguing that most companies get her wrong.
O'Leary has a statistic she comes back to in interviews, and it is the closest thing she has to a thesis. More than 80% of mothers start out breastfeeding. Fewer than half reach their own breastfeeding goal. Her reading of that gap is not that mothers quit. It is that they were never set up to succeed.
The last number is the one that seems to bother her most. Prenatal care checks on a mother weekly, sometimes daily. After the birth, the system often offers a single visit around the six-week mark, and then she is on her own. O'Leary points at that drop-off and calls it what it is: a structural failure that products and policy have both been slow to fix.
What makes the line land is who is saying it. This is the chief executive of a breast-pump company telling you the category has been failing its customers. She does not soften it into a marketing promise. She uses it as the reason the company should exist.
Ask O'Leary what she is proudest of and she does not reach for a revenue figure. "What I'm most proud of with Willow is that we have pushed the world to think about the new mother as deserving of being the center of the products built for her," she has said. It is a reframe more than a feature list, and it runs straight through how she talks about her own life as a mother of two.
Most workplaces still price motherhood as a cost, something to be managed around. O'Leary built a business on the opposite bet, and then backed the slogan with policy. She has talked about leading paid-family-leave standards inside Willow and choosing values-aligned venture partners rather than taking money from anywhere it was offered. The tell of whether a company means "moms first" is not the tagline. It is whether the parental-leave document agrees with it.
She is also willing to say things that cut against her own sales pitch. Mothers, she has argued, need to know it is okay to combination feed, or to stop breastfeeding entirely if they are struggling. A breast-pump CEO telling you it is fine not to need her product is a strange kind of marketing. It is also the kind that builds trust you cannot buy.
On December 19, 2023, Willow named O'Leary chief executive. What is notable is the route. She did not arrive from outside with a mandate to fix things. She moved from VP of Growth to chief marketing officer to chief commercial officer to CEO, learning the customer at each rung before taking the next one. "It's a tremendous honor to be appointed as CEO and have the opportunity to lead Willow into its next chapter," she said at the time.
Along the way the company changed shape. Willow started as an e-commerce story: a single, striking hardware product sold directly to mothers online. Under O'Leary's commercial leadership it became omnichannel and broader than the pump itself, expanding into accessories, education and an ecosystem aimed at the whole feeding journey rather than one device.
In 2025, Willow acquired Elvie, the British femtech company whose own wearable pump had made it one of Willow's most visible competitors. TechCrunch reported the deal as an asset purchase, with Elvie moving into administration, the UK version of bankruptcy. For O'Leary it was less a rescue than a strategy she had been describing out loud: an opportunity to accelerate toward global scale and a more diversified product portfolio through acquisition.
The combined company folds two of femtech's best-known brands into one platform, with a wider product range and global distribution. It is the kind of consolidation that is easy to announce and hard to run, and it is now the defining test of her tenure. Two rival cultures, two product lines, one mission that has to be big enough to hold both.
O'Leary tends to talk about mothers the way someone talks about people they actually know. When Willow ran a survey on what makes new mothers feel strong, her takeaway was not a product angle. "Motherhood is filled with real moments of strength," she said, "but we've built a culture where we've normalized their triumphs to the point that they are dismissed as routine." Women, she added, are expected to do the extraordinary quietly and often unseen.
It is a consistent throughline. A consultant's eye for the number that matters, a brand builder's instinct for what people feel, and a mother's refusal to let the hard parts go unnamed. She sells a device that lets a mother pump discreetly, hands-free, without being tethered to a wall. The larger pitch is that the person using it deserves to be designed for in the first place.
Whether the Willow-Elvie combination holds is a question only the next few years answer. What is already clear is the frame O'Leary has spent her career installing: the new mother is not the afterthought a product serves. She is the reason it gets built.