Sarah O’Leary: CEO of Willow Innovations
Second Life
Who What Wear
4.7 • 3K Ratings
🗓️ 15 September 2025
⏱️ 56 minutes
🧾️ Download transcript
Summary
Sarah O’Leary is the CEO of Willow Innovations, the inventors of the first wearable breast pump. She began her career as a consultant for private equity clients, learning firsthand how businesses make big decisions and developing her problem-solving skills. She then made the switch from advising companies to helping run them when she went to work for a client. O’Leary transitioned into brand development and growth in the e-commerce and retail space at companies of all sizes, refining her skills. Willow Innovations reached out to her to recruit her shortly after she became a mom. The offer came while she was navigating postpartum life and reconsidering how she wanted to invest her time. She accepted Willow’s offer because she believed in the company’s commitment to showing up for moms like her. O’Leary joined as the company’s vice president of growth, helping expand Willow’s product offerings and its identity as a brand that supports moms beyond breast pumps. The results she drove and her years of experience made her the perfect candidate for the role of CEO when the time came to select a new one.
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Transcript
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| 0:00.0 | Your first great love story is free when you sign up for a free 30-day trial at audible.co. |
| 0:05.5 | That's audible.co.uk slash wondering. |
| 0:12.1 | Hi, everyone. I'm Hilary Kerr, the co-founder and chief content officer of Who What Where, and |
| 0:22.2 | this is Second Life, a podcast spotlighting women who have truly inspiring careers. |
| 0:29.0 | We're talking about their work journeys, what they've learned from the process of setting |
| 0:32.8 | aside their doubts or fears, and what happens when they embark on their second life? |
| 0:38.5 | Today on the show, I'm speaking with Sarah O'Leary, the CEO of Willow Innovations, |
| 0:43.9 | which is the company behind the first ever fully wearable breast pump. |
| 0:49.0 | Sarah began her career working as a consultant, but after getting her MBA, she transitioned into a business and sales |
| 0:56.0 | development role at a skincare company that was a former client of hers. From there, she went on |
| 1:01.9 | to lead marketing, strategy, and sales at T Collection, a kid's fashion brand, where she realized |
| 1:07.6 | she found a lot of joy working on a brand that she truly loved. |
| 1:11.9 | So, when she was approached to join a new startup called Willow, |
| 1:15.7 | she couldn't say no to the opportunity to work for a company with such an important mission, |
| 1:21.2 | putting moms first. |
| 1:23.1 | Sarah began as the company's vice president of growth and grow the company she did. |
| 1:28.4 | Under Sarah's leadership, Willow has expanded its product offering, centering moms in their postpartum journeys |
| 1:33.5 | beyond breast pumps, and earlier this year, the brand acquired Femtech company LV, which is |
| 1:39.5 | expected to increase the overall company's revenue by 50%. Sarah has held a number of roles at Willow from VP of Growth to chief marketing officer |
| 1:48.3 | to chief commercial officer and now finally CEO. |
| 1:53.0 | Her journey is so inspiring and I can't wait for you to hear this episode. |
| 1:57.4 | Now, on Second Life, it's Sarah O'Leary. |
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