Sarah O’Leary: CEO of Willow Innovations
Second Life15 Syys 2025

Sarah O’Leary: CEO of Willow Innovations

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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Jessica Yellin: Journalist, Author, and Former CNN Chief White House Correspondent

Jessica Yellin: Journalist, Author, and Former CNN Chief White House Correspondent

Where do you get your news? If Jessica Yellin's Instagram isn't at the top of your list, it will be soon. The former chief White House correspondent for CNN and founder of #NewsNotNoise tells Second Life how she took her Emmy-winning reporting skills to both social media and book publishing.

25 Maalis 201952min

Sophia Roe: Chef, Wellness Expert, and Content Creator

Sophia Roe: Chef, Wellness Expert, and Content Creator

Sophia Roe's passion for food and wellness started as a distraction from her tough childhood. Growing up with parents who were substance abusers and eventually ending up in the foster care system, Roe found comfort and stability in both food and music. In the new episode of Second Life, Roe tells Hillary Kerr about overcoming unconventional beginnings, dropping out of college twice, and becoming a chef, wellness expert, and thought leader.

18 Maalis 201949min

Veronica Swanson Beard & Veronica Miele Beard: Veronica Beard Co-Founders

Veronica Swanson Beard & Veronica Miele Beard: Veronica Beard Co-Founders

Armed with experience in finance and fashion buying, respectively, sisters-in-law Veronica Miele Beard and Veronica Swanson Beard started their fashion brand with a single jacket style and no business plan. A decade later, they have a successful label with seven brick-and-mortar stores. Here, they speak about working with a business partner, learning to trust your gut, and the question Anna Wintour asked them.

11 Maalis 201954min

Susan Tynan: Framebridge Founder and CEO

Susan Tynan: Framebridge Founder and CEO

All of our guests have changed careers at some point, but Susan Tynan's path took several different turns on her way to raising $67 million in venture financing for Framebridge, a quick and affordable custom framing site. The founder and CEO, a Harvard Business School graduate, shares advice on how to accept "no" in your career, how to run a business ethically, and how to lift women up.

4 Maalis 201940min

Nancy Silverton: Celebrity Chef, Restaurateur, and Author

Nancy Silverton: Celebrity Chef, Restaurateur, and Author

It started with a crush. Renowned chef, restaurant owner, and author Nancy Silverton first developed an interest in the food industry because she had a crush on a student cook at the dining hall of her college dorm and convinced him to hire her in the kitchen. Learn how she went from being a pastry chef to running her own empire and winning the food industry's highest honor.

25 Helmi 20191h 1min

Raissa Gerona: Revolve Chief Brand Officer

Raissa Gerona: Revolve Chief Brand Officer

L.A.-based retailer Revolve paved the way for influencer trips that now take over your Instagram feed, and Raissa Gerona is the brains behind the site's innovative strategy. Early in her career, she dealt with her parents' disapproval of her career path and a business failure, but you can bet she learned a thing or two on her way to becoming Revolve's chief brand officer.

18 Helmi 201946min

Sara & Erin Foster: Bumble Heads of Creative

Sara & Erin Foster: Bumble Heads of Creative

Erin and Sara Foster are nothing if not honest. In the newest episode of Second Life, the sisters get real about feeling in over their heads, pursuing careers that paid the bills but weren't fulfilling, and regretting not going to college. Whether you know the Fosters from their parody-reality show on VH1, Barely Famous, or from their current positions as the heads of creative at Bumble, you'll learn a whole new side to the sisters.

11 Helmi 201949min

Shiona Turini: Stylist and Costume Designer

Shiona Turini: Stylist and Costume Designer

Shiona Turini has the résumé that anyone with a dream of working in fashion envies. In episode 50 of Second Life, she shares what she learned cutting her teeth at the industry's major print magazines before fearlessly moving into freelance styling and finally transitioning into costume design for HBO's acclaimed tv series Insecure.

4 Helmi 201951min

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