Sarah O'Leary remembers looking at the app that tracked her nursing and pumping hours after her first child was born. The number stunned her: 1,800 hours in a single year. That's equivalent to a full-time job.

Join Bora Celik as he chats with Sarah O'Leary, CEO of Willow.

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"It's almost astonishing to think how I spent that many hours in this feeding and pumping experience," she says, reflecting on those early days of motherhood.

For decades, breast pumps remained essentially unchanged - bulky devices with tubes, bottles, and cords that tethered new mothers to walls. They worked, technically speaking. Milk was extracted. But they completely ignored the needs of the women using them.

That's where Willow comes in.

From Tea Collection to Transforming Motherhood

Before joining Willow as CEO, O'Leary worked at Tea Collection, a children's apparel brand focused on global curiosity. While she loved the company, when the opportunity to join Willow appeared, she couldn't resist.

"As beautiful as a children's dress may be and the memories you can build when your kids are wearing clothing that you're proud of and that has a deeper story behind it, the opportunity to actually work on a product that fundamentally improved the experience of a new mom's postpartum journey sort of took that to another level," O'Leary explains.

Willow invented the first all-in-one, in-bra wearable breast pump. No tubes. No cords. No bottles hanging off your body. Just a sleek device that fits inside a nursing bra, allowing moms to move freely while pumping.

Starting with Moms, Not Technology

Unlike most medical device companies, Willow didn't start with cool technology looking for a problem to solve. They started by asking what new mothers actually needed.

"A unique aspect of the culture of innovation that we grew out of is a user-centric, needs-oriented design process," says O'Leary. "It really did start with, if we want to make a positive impact for new moms, let's listen to what they need."

The result was four years of intensive R&D before launching their first product at CES in 2017. They studied what happens biologically when a baby latches to the breast and designed technology to replicate that process - all while making it small enough to fit into a bra.

The $500 Gamble That Paid Off

When Willow launched, their pump cost $499 - significantly more than traditional pumps, which many women got for free through insurance. Yet something remarkable happened.

"What was remarkable is that essentially in that trade from spending $0 to having to spend $500, women made the trade," O'Leary says. "It was almost like people voting with urgency for a solution that actually met their needs."

Today, more than half of breast pumps sold are wearable - a testament to how transformative this innovation has been. And while Willow continues to work on making their products more affordable (their Willow Go is now $349), that initial price point revealed something important: mothers were willing to invest in technology that genuinely improved their lives.

Building Community Through Authenticity

The Willow Moms Facebook community has become a place where women share not just their successes but also their struggles. This open dialogue helps Willow understand what mothers truly need.

"We really work to hear and to project back not only the stories of success in breastfeeding or the best pumping session I ever had," O'Leary says, "but also like what's normal? Most women pump four ounces every time that they pump, that doesn't fill up the pump and that's totally normal and you're doing great."

This authenticity extends to their marketing partnerships too. Rather than just giving away free products hoping for mentions, they look for genuine connections.

"We are really excited about partnering with creators, but we're looking to make sure that your story is a genuine representation of how our product fits into your life," says O'Leary.

Looking Beyond Pumping

Willow has made a deliberate choice to focus deeply on the postpartum period rather than trying to follow mothers throughout their children's lives.

"Postpartum is a pretty unique and pretty all-encompassing shift in life, and we think we can be a partner along that journey," O'Leary explains.

They've expanded into partnerships with companies providing lactation services, mental health support, and pelvic floor recovery - all accessible through their app. But they remain committed to the postpartum period, believing there's still much more to do in this underserved space.

The Human Touch in an AI World

As artificial intelligence transforms marketing and customer service, O'Leary is thoughtful about where to use it and where not to.

"We have Willow mom coaches who do video appointments with moms who need help with their pump," she says. "They're struggling, right? They're in a very vulnerable moment and they need that human interaction as much as they need help with the pump."

While they've implemented AI tools in their app to provide science-backed information, Willow knows some moments demand a human connection.

Looking Ahead

As Willow continues to innovate, O'Leary is excited about the company's advocacy work with Chamber of Mothers, a nonpartisan group advocating for policy changes that support women and families.

"A lot of what I see our mission being is improving the postpartum experience. There's lots we can do with products and technology, but there's also a lot that we can do to advocate for social change."

For too long, the needs of postpartum women have been overlooked. Willow is changing that, one pump at a time.

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