Welcome to Second Life, a podcast spotlighting successful people who’ve made major career changes—and fearlessly mastered the pivot. Hosted by Hillary Kerr, co-founder and chief content officer at Who What Wear, each episode gives you a direct line to people who are game changers in their fields. Subscribe to Second Life on Apple Podcasts, Spotify, or anywhere you get your podcasts to stay tuned.
Sarah O’Leary, the dynamic CEO of Willow Innovations, has redefined the femtech landscape by leading the company behind the world’s first fully wearable breast pump. With a career rooted in strategic leadership and a deep commitment to empowering mothers, O’Leary has transformed Willow into a beacon of postpartum support.
O’Leary’s career began in consulting, where she honed her analytical and problem-solving skills. After earning her MBA, she transitioned into business and sales development at a skincare company, a former client, marking her shift into consumer-focused industries. She then worked at Tea Collection, a children’s fashion brand—ultimately, becoming a pivotal moment for her. As head of marketing, strategy, and sales, she discovered her love for working on brands that resonate deeply with their audience.
Then, in 2014, O’Leary was approached by Willow Innovations, a startup with a bold mission: to put moms first. She joined as Vice President of Growth, drawn to the opportunity to revolutionize the breastfeeding experience. Willow’s groundbreaking wearable breast pump, designed to offer freedom and flexibility, quickly gained traction under her strategic vision. O’Leary’s ability to connect with consumers and scale operations propelled Willow’s growth, expanding its product line to support moms beyond pumping, addressing broader postpartum needs.
Willow Pump
Willow Go Wearable Breast Pump
From VP of growth, she moved to chief marketing officer, then chief commercial officer, before assuming the role of CEO. Each position showcased her ability to blend innovation with empathy, ensuring Willow’s offerings remained mom-centric. With O’Leary at the helm, Willow also acquired Elvie earlier this year, a fellow femtech pioneer, solidifying its position as an industry leader.
Listen to the latest episode of Second Life to hear how, under O’Leary’s guidance, Willow has become a holistic platform for maternal wellness.
Next: Meet Sarah Harrelson: The Visionary Founder and Editor in Chief of Cultured Magazine
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