Sarah O’Leary: CEO of Willow Innovations

15 Sep 2025 · 56 min · 29 chapters

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In short

Sarah O’Leary’s career journey to becoming CEO of Willow Innovations, and how Willow is redesigning postpartum support through wearable breast pumps plus connected services, accessories, and policy advocacy. She also discusses her shift from consulting to operating roles, and Willow’s acquisition of LV to expand into pelvic floor recovery and postpartum sleep products.

Guests (1)

Sarah O’Leary, CEO of Willow Innovations. Background: English major; started at The Parthenon Group (consulting) doing consumer insights, financial modeling, and growth strategy for private equity due diligence. Earned an MBA, then joined StriVectin (operating role) after due diligence work; later moved to Tea Collection (kids apparel) for marketing/strategy/sales. Joined Willow as VP of Growth (e-commerce and digital marketing), later led marketing, commercial functions, and became CEO.

Key claims

Breast pumps should be designed “for moms,” not just baby; postpartum support in the U.S. is inadequate; Willow’s mission is to center women’s full postpartum journey. LV acquisition is expected to boost revenue by 50%.

Notable examples

Willow’s 2017 CES launch of the first all-in-one wearable breast pump; her own experience pumping after her son’s birth; app-connected guidance, lactation/mental health support; LV Trainer (pelvic floor recovery) and LV Rise (bassinet rocker).

Written by AI. May contain mistakes. Listen to the episode to check what was said.

Chapters

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Sarah's Early Education and Career Aspirations

1:46 to 2:54

Discover Sarah's diverse academic interests and her early uncertainty about her career path.

“So we like to start at the beginning on this podcast.”

Transitioning into Consulting Work

2:54 to 4:20

Explore Sarah's decision to enter consulting after college and what that experience taught her about business.

“I absolutely understand that there are certain tracks where it's like, you should probably pick a lane if you think you want to go into X, Y, and Z, but I fully agree with you.”

Insights Gained from Consulting Experience

4:20 to 6:15

Learn about the skills Sarah developed in consulting and how they shaped her understanding of business problems.

“So actually learn business by working in business as opposed to in the classroom.”

Lessons from Evaluating Businesses

6:15 to 8:13

Understand how Sarah's work in private equity helped her learn what makes businesses successful.

“Tell me about those early days and some of the clients you were working with.”

Deciding to Pursue an MBA

8:13 to 10:56

Hear about the motivations behind Sarah's decision to get her MBA and how it influenced her career.

“You know, and I think, as I mentioned, there's almost this simplicity to what's going to make a business successful.”

Returning to Consulting After MBA

10:56 to 13:17

Discover why Sarah returned to her consulting firm post-MBA and the financial considerations involved.

“So many people have gotten their MBA who have come on this podcast and very few people talk about the classwork.”

Making the Move to Strivectin

13:17 to 14:00

Learn about Sarah's decision to leave consulting for a role at Strivectin and the relationships that facilitated this transition.

“So after you went back, you ended up making a move eventually to Strivectin.”

Transition from Consulting to Management

14:00 to 15:12

Learn about the natural evolution from consulting to an operating role and the importance of relationships.

“buy side and the sell side due diligence for that.”

Adjustments in Operating Roles

15:12 to 16:40

Explore the learning curve and cultural adjustments faced when moving from consulting to operating roles.

“So how did the idea of working for one of the clients match the reality of it?”

The Challenges of Team Dynamics

16:40 to 19:16

Understand the dynamics of working in management and the challenges of differing perspectives in a team.

“you have to make decisions so much faster with so much less information and really start to learn how to kind of navigate making hard choices without a whole consulting team helping you.”
Show all 29 chapters

Career Reflection and Networking

19:16 to 19:56

Discover the importance of reflection and networking in career transitions.

“And how do you take your learnings and move on to the next thing?”

Joining Tea Collection: A New Chapter

19:56 to 21:14

Learn about the decision to join Tea Collection and the alignment of skills with company needs.

“really getting to know interesting people in the Bay Area who were working on consumer businesses at relatively early stages.”

Experiences at Tea Collection

21:14 to 23:37

Delve into the operational challenges and the excitement of brand development at Tea Collection.

“And maybe this is an opportunity for us to move forward together.”

Introduction to Willow Innovations

23:37 to 24:49

Get an overview of Willow Innovations and the innovative product they introduced to the market.

“out of a medical device incubator, if memory serves.”

Personal Connection to Willow

24:49 to 26:09

Hear about the personal journey and transformation that influenced the decision to join Willow.

“So I had experienced all of the challenges of new motherhood, of going back to work as a new mom, of trying to figure out how to pump and breastfeed and do all of the things that were expected of me in this new role.”

Role and Responsibilities at Willow

26:09 to 28:01

Explore the responsibilities of the VP of Growth and the unique challenges faced in a startup environment.

“me, this is an opportunity that could be really, really interesting as a shift and a change.”

Transitioning to a New E-commerce Role

28:01 to 29:09

Learn how Sarah O’Leary shifted from a broader scope to a focused role at Willow Innovations.

“And it's interesting because in so many ways, it was actually sort of a downgrade in terms of scope.”

Adapting E-commerce Strategies for a New Product

29:10 to 30:45

Explore how marketing strategies differ when selling high-consideration products like breast pumps.

“I think of it as the tools are all the same and you're just turning the dials differently, right?”

Navigating Startup Culture as a New Leader

30:46 to 32:50

Understand the unique challenges and experiences of transitioning to a startup environment.

“As someone who had come in from more established corporate legacy companies, how did you find the culture of a startup?”

Evolving Roles and Career Growth at Willow

32:51 to 35:51

Discover how Sarah's roles evolved at Willow from VP to CEO and the importance of mentorship.

“I was, you know, happy to do that because I was so excited about where the company could potentially go.”

Unexpected Path to CEO

35:52 to 37:05

Learn about the circumstances that led Sarah to become the CEO and her reflections on the role.

“I was really happy in my functional area.”

Putting Moms at the Center of Product Development

37:06 to 39:20

Explore Willow's mission to enhance the postpartum experience for mothers through innovative products.

“having gone through it myself, having observed it in others.”

Comprehensive Support for New Mothers

39:21 to 41:45

Learn about Willow's range of products and services designed to support mothers in their feeding journey.

“And having had this experience twice, there is nothing as transformative that I've ever encountered in my life than becoming a mother.”

Strategic Acquisition of Elvie

41:46 to 42:04

Gain insights into the acquisition of Elvie and its implications for Willow's growth and market presence.

“So that's really kind of what we've been up to with lots of exciting product launches and newness ahead.”

The Acquisition of Elvie

42:04 to 44:44

Sarah O’Leary discusses the acquisition of Elvie and the vision behind the merger.

“So Willow launched our wearable breast pump in 2017.”

Advocating for Parental Policies

44:44 to 47:21

Sarah shares her views on advocating for better parental leave and childcare policies.

“and we're fueled by this passionate belief that we can do better for women and the world would be better off if we could embark on that project together.”

Navigating Mistakes and Challenges

47:21 to 50:00

Sarah reflects on mistakes in her career and the lessons learned from them.

“But it's also like, I just birthed a baby.”

Advice for Career Pivots

50:00 to 52:14

Sarah offers insights and advice for those considering a career change.

“and they know that they want to make a change, whether they want to stay in their same industry and do a different aspect of it, or they want to change companies or they want to start something, but they're scared.”

Empowering Your Future Self

52:14 to 54:26

Sarah discusses self-limiting beliefs and the importance of striving for big goals.

“So my last question is also my favorite, which is if you could get in the time machine and go back and speak to your younger self and give your younger self some advice, what would you say?”
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Transcript

Automatic transcript. May contain errors.

0:04Hi, everyone. I'm Hilary Kerr, the co-founder and chief content officer of Who, What, Where, and this is Second Life, a podcast spotlighting women who have truly inspiring careers. We're talking about their work journeys, what they've learned from the process of setting aside their doubts or fears, and what happens when they embark on their second life. Today on the show, I'm speaking with Sarah O 'Leary, the CEO of Willow Innovations, which is the company behind the first ever fully wearable breast pump. Sarah began her career working as a consultant, but after getting her MBA, she transitioned into a business and sales development role at a skincare company that was a former client of hers.

0:48From there, she went on to lead marketing, strategy, and sales at Tea Collection, a kid's fashion brand, where she realized she found a lot of joy working on a brand that she truly loved. So when she was approached to join a new startup called Willow, she couldn't say no to the opportunity to work for a company with such an important mission, putting moms first. Sarah began as the company's vice president of growth and grow the company she did. Under Sarah's leadership, Willow has expanded its product offering, centering moms in their postpartum journeys beyond breast pumps. And earlier this year, the brand acquired femtech company LV, which is expected to increase the overall company's revenue by 50%.

1:31Sarah has held a number of roles at Willow from VP of Growth to Chief Marketing Officer to Chief Commercial Officer, and now finally, CEO. Her journey is so inspiring, and I can't wait for you to hear this episode. Now, on Second Life, it's Sarah O 'Leary. Sarah, are you ready to start? I'm ready. Okay, excellent. So we like to start at the beginning on this podcast. So what did you study in school? And much more importantly, what did you think you were going to be when you grew up?

2:06Sarah O’Leary:I think first of all, I was always a student. I loved school. I studied everything. You know, I love my biology teacher. I was going to be a pre-med student. I loved math and art. I should be an architect. So I was not somebody who knew early on this was going to be my career. I was very much kind of led by my academic interests, I guess. in college. I ultimately majored in English, but it was a bit of a journey for me to kind of get to that commitment. And it really wasn't about a career aspiration for me at that time. It was almost completely separate. And I think there's almost maybe too much dialogue about liberal arts and how that turns into a career today.

2:44Sarah O’Leary:And I very much had the opportunity to explore what interested me without necessarily tying it to a specific career objective at that time in my education. I absolutely understand that there are certain tracks where it's like, you should probably pick a lane if you think you want to go into X, Y, and Z, but I fully agree with you. I think one of the greatest luxuries I have about going to school in the late nineties and early aughts was that was not a huge part of the conversation. Like I had the luxury to learn for the sake of learning. And as a fellow English major, you're going to need to read and write and communicate for the rest of your life.

3:20It's going to be fine.

3:21Sarah O’Leary:And you're so young. When I look back at myself at 17, 18, I really was not yet fully formed. And I think the opportunity to explore who that was going to be was just this real gift. Now that we said that, let's go back to brass tech. So talk to me about your first post-college job. What were you looking for? What were you thinking about? What was your plan? Yeah. So with all of that lovely stuff said about the liberal arts, I definitely hit a point in college where it was like, wait, I do need to get a job. I do you need to figure out what I'm going to be when I grow up. And I was pretty certain that wasn't going to be an academic.

3:56Sarah O’Leary:And so I explored a couple of kind of more practical paths. I thought about like many English majors going into a law school path, kind of wanted to get out in the real world and not necessarily just go back to school again. And I wound up interviewing with and really being compelled by consulting firms. So there were some strategy consulting firms that recruited at my college campus. And it felt like this opportunity to learn again, but in a different kind of hands-on context. So actually learn business by working in business as opposed to in the classroom. And so that's ultimately where I ended up right out of college was a firm called the Parthenon Group working in Boston.

4:37So what did that day-to-day entail? Because I've spoken to a lot of people who worked as consultants and I find it so fascinating that, you know, especially as an entry-level job, it's a gift because you're looking at things with fresh eyes, but also there are sometimes pitfalls that come along with like not necessarily having experience. So what was it like for you?

4:57Sarah O’Leary:Yeah. You know, it's really an apprenticeship kind of model. You know, you're on a team that has, you know, a senior partner who absolutely has been working in these spaces for a long time. And then you're all the way at the bottom of the totem pole as your entry-level analyst. And really a lot of the work is teaching you how to think about business problems with all the same skills you learned in school. So I did a lot of consumer insights work. I did financial modeling and building Excel models. A lot of it is you're making PowerPoint slide decks and trying to craft a cohesive story about the project that you're putting together.

5:30Sarah O’Leary:So there's a lot in common with academic work, honestly. Also a good skill set to have. Yeah, exactly. And what I loved was it did give me this opportunity to go from project to project, to learn about different industries, and to start to piece together what's the same every time, what's different, what's unique. How do you start to really understand these trends in a business and how companies are navigating through these kind of stage specific moments? So I did a lot of growth strategy work and you start to see a pattern, right? Like there's only a couple of different ways you can grow. And how do you start to look at that over and over again?

6:07Sarah O’Leary:And I think consulting was a really great way to start to build that pattern recognition, which has been a really valuable element of, you know, my own business education in life. Tell me about those early days and some of the clients you were working with. And if there were any lessons that you learned, like, I'm definitely interested in this, or I am absolutely not interested in this area of business. Like what were some of those early learnings? Yeah. You know, I, to this day, I'm still a recovering English major, you know, so there were certain things that did appeal to me more than others, and some that I think I probably got a bit pigeonholed into as well.

6:43Sarah O’Leary:So I was often the person who was maybe doing the qualitative consumer insights work versus necessarily the econometric model based on some of the work I had done in undergrad. But I naturally really gravitated to consumer businesses and consumer brands. And I think sort of the through line from what I was interested in in school was what makes people tick? What makes people buy things? What's the human story underneath whatever somebody is selling? That was really the work that I was most excited about and engaged in. And I fell into, partly because I was a dedicated student and wanted to work as hard as the company would allow in some sense, but I fell into our private equity consulting group, which basically meant that I was working with private equity firms as clients on evaluating investments that they were going to be making.

7:34Sarah O’Leary:It was very intense work because they would tend to be these really short, intensive projects as a company was doing a due diligence, should we invest in this business? But it gave me an even more accelerated education in what to look for to evaluate a business. Then ultimately, a lot of those investments and the clients that we were working with were investing in growing consumer products companies. And so that became kind of this niche, but it was also a space that I kind of naturally gravitated to anyway. So it was this good fit for kind of learning a lot, but also getting exposure to companies at a stage and a category that naturally fit with my interests.

8:15To get a behind the scenes peek at how businesses are really evaluated and what makes them compelling, no matter if you are starting a business or looking at companies to work for, like that is really good data and insight and gives you such a leg up as you're navigating your own career, I would think.

8:33Sarah O’Leary:I think that's right. You know, and I think, as I mentioned, there's almost this simplicity to what's going to make a business successful. And it's like, is it growing? And there's only a couple of ways to grow. You know, you add products or you add distribution, like that's it, you know, more customers, more stuff to sell to customers. Like that is kind of the core model. And can you predict if that's going to hold on? Well, do customers really love this brand? How do we start to understand kind of the momentum behind the authenticity behind growth. And similarly, is the business profitable? Is it making money?

9:06Sarah O’Leary:And are there opportunities to expand that? It's very basic, simple stuff, but I think sometimes can get lost in the complexity of a given industry. And there's something about seeing that playbook repeated from an investor's perspective that in some sense is a little cold hearted, but it's also very much the core of what matters. And I think I got that exposure really early on and has kind of given me these like frameworks for how to think about problem solving. Yeah, it is interesting. It's like, okay, if you see the same playbook over and over again, it makes you realize like the numbers just have to work.

9:40And if the numbers work, then everything else kind of flows from that. Obviously brand is important. Obviously positioning is important, but at the end of the day, is the business viable or not.

9:50Sarah O’Leary:Yeah, exactly. And we all get so tied up in what's unique about our categories and our industries. And believe me, my day-to-day is very much about solving the unique problems that are only facing our company. But at some point, there is this broader pattern. And I think having that perspective is very helpful context. So at what point did you decide to go back and get your MBA? Yeah. So I, again, had this, some of a self-doubt, I think, in that I hadn't trained in business in college. I was learning on the job and I think really had this sense of, is this where I'm going to stay? I had plenty of late nights in consulting.

10:30Sarah O’Leary:It's not an easy hours kind of job where I'd be like, I think I should call it quits and go back and be a professor, something that was a little more back in my comfort zone in school, but ultimately decided that if I was going to give the business path my career, then I needed to get the credential of an MBA. And so I do think a lot of that was driven by some amount of imposter syndrome as much as it was the real need for that degree. I feel like the business world wants us to all think that. I know. It's interesting. So many people have gotten their MBA who have come on this podcast and very few people talk about the classwork.

11:05It is a signifier externally. The networking piece of it seems to be quite useful. It gives you time to make a pivot if that's what you're interested in doing. Was that what your experience was like? It was.

11:17Sarah O’Leary:And again, I really loved school. I was really focused on the academics and I was like, well, this will be great. I'll take accounting classes and I'll take macroeconomics and I'll make sure I've learned all those things. And what was so interesting that probably also helped cure that imposter syndrome is that I took that coursework and I did well in it and it was fine, you know, and it was like, oh, there's not some big mystery here. And a lot of what I learned in my work was very much the same things I learned in the classroom. And so it kind of helped me, I think, almost just alleviate that burden for myself as much as anything else.

11:53Sarah O’Leary:And that's no knock on the curriculum. It was great, but I didn't have to get it that way necessarily. And I did certainly get a lot of other benefits from those two years that weren't just what was in the academic curriculum. You went back to your same company post-grad. What made you decide to do that? And were there more opportunities on the other side? Yeah. So I very transparently went back largely as a financial decision. It was a practical decision. My firm covered the cost of tuition if you came back and worked afterwards. So So that was a tough one to pass up. Yeah. So it was definitely part of the equation.

12:31Sarah O’Leary:I explored the possibility of just moving on to a different career path straight out of school and had some extremely exciting opportunity that I was really passionate about come up. I might have made that decision, but I liked the work in consulting and I did get to go back and operate at a different level of seniority that I think continued to accelerate my learning. So I really view almost that first seven years of my career as this almost one cohesive learning opportunity at different levels and with different levels of academic credential. But in some sense, a fairly continuous chapter, I think, but getting to see things and really solidify my learning and understanding of the business problems that I was solving from a lot of different angles.

13:17So after you went back, you ended up making a move eventually to Strivectin. Talk to me about making that decision. I'm always curious about that inflection point in someone's mind. Like what makes them decide, I'm going to start looking. And then what makes them decide this is the time and this is the place?

13:37Sarah O’Leary:I ended up actually joining a client company. So Strivectin, I worked on the due diligence for that company. I worked with the firm that invested in that brand and actually worked with the woman who became the CEO at Strivecton on a couple of other projects while I was in consulting for different companies. She had run the Frederick Fakai hair care brand, and I had worked on the buy side and the sell side due diligence for that. So essentially, I had built this really fantastic working relationship and had the opportunity to then leave consulting and join the management team offered to me. And I think that when you have these natural evolutions in your career, it makes those choices really easy.

14:22Sarah O’Leary:It was one of those moments where it was like, this is the right next step for me to, you know, I can close this chapter of consulting. And I think I've learned a lot of what I was there to learn and now try on for size, what it's like to be on the operating side of the business with a team that I had already built a relationship with and built trust with. I mean, that's the dream, right? Yeah, it was in some sense, like the most no brainer part of my whole career. I remember I had a pro and con list that I wrote out about like, should I take this job? And there's one con, which was I was living in San Francisco at the time, and the job was in New York.

14:57Sarah O’Leary:And it was like, I like the West Coast. And it's like, this isn't enough to not say yes. So you know, I think, again, it was one of those really natural evolutions and built off of the strength of relationships that I had developed in my work to date. So it was a fun one. That was an easy one. So how did the idea of working for one of the clients match the reality of it? What was your personal experience? Like what was different? Was there a learning curve? Was there culture shock? Definitely a learning curve and some amount of culture shock and not really about the people that I was working with.

15:30Sarah O’Leary:You know, there was probably mostly good surprises in terms of how great you can sort of be enmeshed together into one business as opposed to diving in and out on a project basis. I think there's a bit of a myth when you leave consulting. It's kind of how they get you to stay, I think, is that you're working with these incredibly smart people. And if you get into an operating role, that's not going to be as consistent. That is not true. So that was not the adjustment. What was an adjustment was I was working with people who were talented in very different ways from me. You're in a consulting firm, everybody's the same.

16:01Sarah O’Leary:They're all sort of like analytical, well-rounded, strategic thinkers. Instead, you got to work with this really diverse team of somebody who's like a brilliant creative director and somebody who's a really amazing CFO and somebody who is thinking through the details of operations and logistics. And so you start to really round out your experience of what that type of team can accomplish together, but also where your role is. So I think that was definitely a bit of an adjustment and one that was incredibly enriching and has kept me in operating roles ever since. And then I think the other piece was I was very hungry to not have what I made be PowerPoint decks, you know, slide decks as a product.

16:40Sarah O’Leary:But the pace of decision making in an operating role versus anything you're doing in client services where you have a whole team dedicated to analyzing a problem for many weeks at a time just isn't what operating a company is like. you have to make decisions so much faster with so much less information and really start to learn how to kind of navigate making hard choices without a whole consulting team helping you. And I think that piece was probably the piece that felt like the biggest adjustment and really quite overwhelming at the beginning. So you stayed at Strifectin for about three years, correct?

17:18I did. Yes. What was going through your mind? What was the catalyst for deciding to look for something different?

17:24Sarah O’Leary:Every good career story has some rocky parts. I actually was part of a management team that was brought in to run the business after it was invested by private equity investor. And we did our best for three years, transformed the business. It was really a turnaround. It was how to take this really interesting legacy brand and modernize it and bring new products into the portfolio. And we did all that work. And at the end of the day, there were some differences in perspective between the management team and the board. the private equity board decided to change out the management team as sort of a pathway forward.

17:57Sarah O’Leary:So I saw very interesting education having kind of worked with private equity clients as my client base and consulting to also see what happens when the going gets tough in an operating environment and how do you navigate differences in perspective between board and management team. And ultimately, I think those are changes that happen all the time in real life and was accelerated out of that role when they changed out the management team. Did you know it was coming or was it surprising? Was it traumatic or like no big deal? The writing was on the wall. So both, it was a little traumatic. I think, you know, we were this really dedicated management team that, you know, was deeply trying to get this business moving in the right direction, had driven a lot of growth.

18:42Sarah O’Leary:You know, it's really proud of the work we've done, And it had some really interesting potential exit opportunities that we thought were real. And to sort of have that not be aligned with the ownership of the business was hard and definitely a bit traumatic. At the same time, it was a long time coming. By the time it actually happened that they were like, we're going to replace out the team, everybody was like, great, it's time. So we're ready to go too. You learn a lot through those experiences about, in some sense, the grown-up reality that things don't always work out exactly as you expect.

19:16Sarah O’Leary:And how do you take your learnings and move on to the next thing? And unfortunately, I've been through lots of business cycles since, and there are ups and there's downs. And I think that was a good lesson to learn reasonably early in my career. I understand that very well. Okay, so you decided to move back to the West Coast, and then what? Yeah, and so I had actually this really amazing experience, which was so many of the choices I'd made in my career up until that point were kind of the next thing came up, right? So I had an offer to join a client company. I had the opportunity to go to graduate school and return to my company.

19:49Sarah O’Leary:So it was really the first time that I had had an open canvas and said, what am I going to do? How am I going to decide what comes next? And so I spent a lot of time really getting to know interesting people in the Bay Area who were working on consumer businesses at relatively early stages. And that was the zone I really loved. And so I said, let me figure out if I can find a role in a brand that I'm going to be passionate about and let's see what happens. And it really came from networking, going back again to that benefits of the MBA. I had a great network to draw from in terms of introductions to people who were doing interesting work and ultimately got connected to tea collection, which is not a tea company.

20:32Sarah O’Leary:It is a beautiful, high quality, but also still affordable children's apparel brand. I own a lot of it. My kids are big fans and so am I. Yes, it's cult following. And T was around for about 10 years when I joined, but was starting to kind of hit its stride in terms of growth for the company and opportunity to really enter its next chapter of growth and maturity. And they were looking for somebody with a strategic background to come in and do very similar work to what I had been doing at Strivectin. And so I had the opportunity to join. It wasn't a role that was posted on LinkedIn. It was sort of, hey, somebody just left and they were doing something similar to you and similar to your background.

21:17Sarah O’Leary:And maybe this is an opportunity for us to move forward together. And ultimately, it was a really meaningful part of my career. Did you feel like you were able to use those skills from earlier in your career to assess the state of the company and make that call? Or was it simply like, oh, these are interesting people and I like the brand? How did you go about assessing the fit? Oh, totally. Asking for all kinds of, you know, I'm under NDA. Can I see the financials for the last few years and really make sure that I was pressure testing the opportunity? Again, was the business growing? Was the profitability there?

21:50Sarah O’Leary:But, you know, I think it is an important piece of anybody's career to make sure that you're joining a company that has that opportunity, right? that isn't just about a great story, but actually has the fundamentals kind of at your back. Of all of the things that you did at T, what were some of your favorite parts? Because you started as the VP of marketing and strategy, ended up leading marketing strategy and sales. That is a pretty all-encompassing remit. What did you enjoy the most? What did you learn the most? What was that time like over those six years? So many of the functional projects I was working were similar to what I had done at Strivectin, but I was now in my second round of an operating role.

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22:31Sarah O’Leary:While I was at T was really when I got to immerse myself as a functional leader, not, oh, you know, she came from strategy consulting, so she can do some operating work, but really it's still doing the math and doing the business strategy pieces. What I deeply loved was the opportunity to lean in on the marketing side and to help build and develop the brand in collaboration with our merchants and in collaboration with our creative team. It was a company that was really fueled by the passion that customers felt for the brand and products. And figuring out how to honor that while also creating growth opportunity for the company was just such a fantastic challenge and also creative and all-encompassing.

23:17Sarah O’Leary:So I would say, looking back, that was the chapter of my career where I got to fully immerse myself in the full scope of an operating role and really kind of roll my sleeves up in collaboration with functional partners that were thinking about things very differently from me to really build a successful path for the company into the future. So in 2017, while you were still in your job, a femtech company called Willow was launching out of a medical device incubator, if memory serves. I'm familiar with Willow, but for anyone in our audience who might not know, can you share a little bit about the company and how they reached out?

23:58Sarah O’Leary:Yeah. So Willow, for those who are not familiar, was the inventor of the world's first all-in-one in-bra wearable breast pumps. So essentially what that means is that breast pumps prior to Willow were typically this kind of big chunky box that sat next to you on the table with a bunch of tubes and cords and dangling bottles. And it's as humiliating as it sounds and as uncomfortable and inconvenient as it sounds. Makes you feel like a cow. Absolutely. It's like technology from the dairy industry. And Willow essentially turned the category on its head at CES, announced the first wearable pump in 2017 and the rest to some extent is history.

24:37Sarah O’Leary:So I had coincidentally just had my first baby. My son was born in 2018. and I did not know about Willow as a new mom. So I had experienced all of the challenges of new motherhood, of going back to work as a new mom, of trying to figure out how to pump and breastfeed and do all of the things that were expected of me in this new role. Obviously worked at a fantastic kids apparel brand. So it was in many ways as supportive an environment as you could imagine, and a really strange and transformative chapter of life that I had just navigated. Separately from the outreach from Willow, actually, I had started conversations with the CEO at T and said, you know, I've been here for six years.

25:22Sarah O’Leary:I don't know if this is where I should spend the next six years. And maybe it's time for me to think about what's next. In large part, really driven by this major life change that forced me to think about, what am I doing? How am I spending my time? It's a reckoning. Yeah. And am I moving forward? Am I growing in professional ways as much as I've just kind of experiences transformation personally. And right around that time, I got outreach from a recruiter who was actually a business school classmate. So there comes that MBA again, asking if I'd be interested in interviewing for this e-commerce leadership role at Willow.

25:57Sarah O’Leary:And I've described a couple of these kind of career transitions as natural or kind of added up from past things. But this one really felt like the stars are aligning here and the universe is telling me, this is an opportunity that could be really, really interesting as a shift and a change. So the role was originally VP of growth, correct? Yes. Yep. What was the ask? What were you meant to oversee? How comfortable did you feel with it? Was it very different from apparel? I'm so curious about what those early days were like. Yeah. So as you mentioned, so Willow actually came out of a medical device incubator, which basically means it was these long-term engineering think tank folks who deeply understood how to build FDA-regulated medical devices.

26:47Sarah O’Leary:Breast pumps are a really interesting category because breast pumps are an FDA class two regulated medical device, but they're also kind of a consumer product in a lot of ways. So most women are buying their breast pump maybe at Target or Walmart, or they're using their insurance benefit, but they're not getting a sort of traditional medical prescription for that. They're sort of saying, I'm pregnant, and your insurance allows you to choose from a set of pumps. So the business model was really a direct-to-consumer, consumer brand-type business model. But the company had been founded by people who were medical device people through and through.

27:26Sarah O’Leary:So essentially, when the product first launched, they were selling it via the website. That was the only way we went to market and pretty quickly recognized that the company needed to start to build out a commercial function that looked really different from what sort of the early founders background and capabilities were. So I joined the company essentially as part of that early commercial team. And my role was VP of growth, but really what that meant was run the e-commerce business and run digital marketing. And they had some contractors doing that work. Nobody really knew how to do that work.

28:01Sarah O’Leary:And it's interesting because in so many ways, it was actually sort of a downgrade in terms of scope. I was running a lot more functions at my prior roles, but I knew e-commerce and digital marketing inside out. And so the opportunity to bring that skillset to a company that was in such a different category and to be able to learn about sort of a truly life-changing product in a category that was so impactful felt totally worth it to me to sort of say, I'm going to reduce my scope, but I'm going to get in at sort of the ground floor of this company that is making such a meaningful impact for women who are, again, at this life stage that I had just navigated.

28:38So what was it like? Because I feel like it's got to be a very different situation when you're operating for a children's clothing company that has 10 plus years of brand recognition versus launching this new brand still essentially where you don't have the same awareness, where you're reaching customers at a vulnerable point in time? How did you navigate your strategy? Because I feel like understanding one is great, but how much did your previous experience with tea collection translate in terms of e-commerce growth?

29:10Sarah O’Leary:I think of it as the tools are all the same and you're just turning the dials differently, right? So a breast pump is a much more considered purchase than a pair of leggings. the price point is a lot higher. And so things like how do we create payment plans or how do we accelerate insurance coverage and those things that help bring affordability down. But at the end of the day, conversion rate on a website is still driven by relative affordability, right? And so some of those same dynamics were still very much in play, but just applied in different ways. And I think really recognizing that, again, the passion of your users and the passion of your customers and really centering the person using your product was lessons I had learned throughout my whole career in consumer products as like what creates durable, meaningful, long-term value.

29:58Sarah O’Leary:And that was in the DNA at Willow from the very beginning. It really was why the company had created a new breast pump was because women were asking for an evolution in this category. They set out to say, let's do a medical device for moms. And people literally said like, I need to talk to you about my breast pump because it so doesn't meet my needs. And I think that was one of the things that I really recognized in the company from the beginning was this deep focus on the woman using the product and designing for her. And that's what you can build a great brand from. When that's so authentic to the company's origins, that's the magic, that's the secret sauce.

30:37Sarah O’Leary:And I think everything else becomes kind of the tactics that you put in place to ensure that you're building the successful business decisions off of that foundation. As someone who had come in from more established corporate legacy companies, how did you find the culture of a startup? I was definitely worried about that when he first took the role because I was like a mom of a one-year-old. I was like, oh, am I going to be able to kind of handle the relative intensity of a startup? There's an intensity to trying to bring something new to the world that, like you said, you have to convince people even what it is.

31:12Sarah O’Leary:people used to say like, well, where does the milk go? Like people didn't understand the product. And so that level of product education, we were really forming from the beginning, but we also were a medical device company. So there's all this like regulatory infrastructure and, you know, sort of requirements that were overlaid on this growing startup. And so it was actually not necessarily a stereotypical startup experience per se. You know, there were elements where we went slower than I expected. There were elements where things moved a lot faster and, you know, we had to problem solve unexpected things more or less constantly.

31:48Sarah O’Leary:But, you know, I think that's also just part of operating any business too, is there's always something that surprises you. And if anything, I would say probably running a business over the last five ish years, no matter what that business was, is probably a more chaotic experience than just the idea of it being a startup. It's like we went from COVID to everything that came after that, now tariffs, and it's been a wild ride. And I'm not sure that that's necessarily worse or better at a startup than anywhere else. Yeah. I keep thinking, I'm like, can we just live in precedented times again? Precedented times.

32:25Sarah O’Leary:We're always wishing for that. So you had a really amazing journey thus far at Willow from VP of growth when you started to chief marketing officer, to chief commercial officer, and finally CEO. What was the trajectory and desire to transform into those different roles? And how did that prepare you for the CEO role? So, you know, as I mentioned, in some sense, I had taken a smaller scope when I joined Willow so that I could join the company. I was, you know, happy to do that because I was so excited about where the company could potentially go. So it was very natural in the earlier years for me to start to take on additional responsibility that matched what I had already been doing in other environments.

33:08Sarah O’Leary:So all the same functions that I had at T, I ultimately took on at Willow, really driven as the company grew. First, we only sold through e-commerce. So that's what my role was. And then we said, now we're going to expand into retail channels. And so I took on hiring a head of sales and driving that piece of the growth for the business. And it was very organic in a lot of ways. As the company evolved, my role and scope also evolved. And I think my approach has always been to sort of raise my hand and say, like, I think I can do that. You know, like, let's figure out how I can play a role. How do I work with my teammates to get to the best outcome for the business?

33:45Sarah O’Leary:And I think that happened really naturally at Willow where there were these opportunities to say, I'm already working on some of these projects together. So why don't we bring this underneath my overall scope and role. I will say I was, and I think this is so important for anybody thinking about their career, I had the support of amazing managers and leaders at the company. So I actually was promoted to the chief commercial officer role very shortly after having my second baby. So I came back from maternity leave and was given the opportunity very quickly to step into that leadership role as my then boss moved on from the company.

34:22Sarah O’Leary:And I think those are always important factors in how you drive a professional and career development is to have those supportive mentors as well. And that was very much true throughout my journey at Willow. I mean, the stats don't lie. Women come back from having children and the three to six month cliff is significant because companies don't understand the need for more flexibility. They don't make it a great return to work environment. There are lots of lots of things going on. And so the fact that you had quite the opposite experience is wonderful and also a testament to the company because it's not the standard.

34:58Sarah O’Leary:I like to think the standard for us is higher given the category that we're in and the change we're trying to make in the world, right, is literally to support women who are navigating postpartum and support their full experience. And it is kind of the core mission of the company. But I don't take for granted that that's something we have to nurture and really put ourselves into a leadership role in all ways, including how we ourselves navigate professional development in our own team. Was becoming the CEO the goal? How did that happen? Was that on the vision board? Was it something you had been striving towards?

35:32What were your feelings on that part?

35:34Sarah O’Leary:No, I was not striving towards it. I definitely did not have anywhere in my sort of aspiration set, like checkbox, I want to be the CEO. I am somebody who kind of takes on responsibility and felt a lot of ownership over my work. Those pieces weren't like a hard no, but it was not sort of my aspiration. I love the commercial functions. I love marketing. I love sales, all those pieces. I was really happy in my functional area. And ultimately our CEO, for a variety of mostly personal reasons, had decided to move on from the company. And another example of where I was given opportunity by colleagues who believed in me, And she recommended that the board consider me as a replacement.

36:15Sarah O’Leary:And the board asked me to step into that role. It was a challenging moment for the company. We purely from like an external fundraising perspective, you know, the last few years for startups with interest rates as high as they are, have been really tough. And so our outgoing CEO had secured funding for the company, but was tired, you know, it was like time to hand the reins over. And so I gave it some really deep thought before saying yes. and in some sense revisited all that internal due diligence, like really made sure I was convinced that I had a vision for where the company could go and that I had after two babies and COVID and all the other things we talked about, that I had the energy to dedicate to this new role and then ultimately decided that, yeah, this kind of did feel like my baby also to some extent and I could be the right person for the next chapter of the company.

37:05I find the transition to CEO a fascinating one, having gone through it myself, having observed it in others. It's such an interesting change, no matter how long you've been at a company or how much experience you have or how well-equipped you are. It's just a different role. It's fundamentally different from anything else. What was the learning curve like for you, or did you feel very well-equipped for it because you had already experienced a significant level of growth within the company?

37:33Sarah O’Leary:Yeah, I definitely think it helped. I knew the company inside and out. I had really seen the company's evolution and growth in a way that very few sort of early employees would have been able to say. So those pieces didn't feel quite so different. I think what continues to be very real to me is the amount of the buck stops here, you know, sort of responsibility that is on my shoulders. And it's true of big things and small things. You know, I have skip levels with the team. and sometimes people are asking me these really intense strategic questions and sometimes they're like, could we get like a better expense reporting platform?

38:09Sarah O’Leary:And sometimes it's like, you know, I don't like how we have to order snacks to the office. You know, like everything kind of comes to you, right? And you realize too that people are really looking to you to understand how you feel because how you feel is a signal for how they should feel. And I think that was always true as a senior leader, but it's even more true when you're in the CEO seat. What I've really reflected on is I don't know that just doing the role at a company that you don't deeply believe in and aren't personally authentically passionate about would be very hard for me. It's hard to kind of play act those pieces of what people are looking for from you.

38:49But I'm fortunate that I couldn't be more passionate about

38:52Sarah O’Leary:what it is we're trying to do in the world. So that piece works. Talk to me about what you're trying to do in the world. Talk to me about product. Talk to me about newness. That part always fascinates me. We have come a long way since reinventing the breast pump. Our business is still today very much focused on breast pumps as our kind of core foundation, but we really do put mom at the center of everything that we built from the inception of the pump all the way through to every product we built today. How refreshing because I feel like it's always about baby. It's never about mom. It is always about baby.

39:26Sarah O’Leary:And having had this experience twice, there is nothing as transformative that I've ever encountered in my life than becoming a mother. And a lot of that for you as a new mom is also about baby, but it's about you too. And particularly in the United States, we do not do a good job of supporting women through this transformative period. Supporting parents in general. Supporting parents, whether that's the sort of social and emotional elements, the physical elements. Most women see their OB once after they give birth and not even all of them do that. And so we really are kind of navigating this chapter as women alone.

40:02Sarah O’Leary:And Willow is essentially, I believe, on this earth to make that better and to really put women at the center of everything we're building. So what that has meant practically for us is a couple of things. We have expanded our pump portfolio to increase affordability of our products since those very early days when it was completely new to the world technology. So really working to give access to more women to willow pumps that enable their breastfeeding journey. We also have built a whole suite of accessory products that help mom in her feeding journey be more successful. Again, reinventing that kind of from her experience out.

40:40Sarah O’Leary:So, you know, you don't have to pour your milk into little bottles and put them in the cooler and then carry the cooler around. You can pour them into a nice looking milk cooler and you're done. You can have a nice looking case. You can have products that were designed with you in mind and you can heal and you can experience this journey, not just as this sort of stressful mess. And you know, the example I've used before is I came home from the hospital and I washed all my pump parts in this like big gray plastic tub that they gave me at the hospital. We still have them. So ugly. Nothing else in my life is like that.

41:17Sarah O’Leary:And there's no need for products that I use to be like that at this moment too, when you are so broken down and you don't feel like yourself. So there's a lot that we're trying to do, which is really just to enable that overall journey. And then our pumps are app connected. So we also have a connected software where we're engaging with mom. We're helping guide her through that journey. We have services, partners, lactation consulting, mental health support, as well as content and resources to help her through that journey. And that's an increasingly big focus for us as well, is really thinking about how do we support the whole woman in this feeding and postpartum journey.

41:52Sarah O’Leary:So that's really kind of what we've been up to with lots of exciting product launches and newness ahead. You also made an exciting announcement recently about an acquisition. Can you talk to me about that a little bit? Yes. So Willow launched our wearable breast pump in 2017. And very shortly after that, out of the UK, a brand called Elvie launched a wearable breast pump in 2018 in the UK and launched in the US in 2019. So we were these two rival companies who at the core were also very much the same, built from this deep, passionate mission about improving access for women to great technology and better products, gentlewomen's competition for many years.

42:37Sarah O’Leary:And then this March, we just announced that we actually acquired LV. We have now become one company and I am very, very excited about what that means for the combined business. LV is based in the UK. And so for Willow, it's an opportunity for us to expand our global footprint, to bring a really exciting product portfolio and product pipeline into the company. So LV has some products outside of the breast pump category. The LV Trainer is a pelvic floor recovery product for urinary incontinence. And then they announced at CES this year, a new product called LV Rise, which is a two-in-one bassinet rocker designed to alleviate the stress of unsafe sleep while also providing parents with a really fantastic rocker experience with interesting technology around soothing built in.

43:30Sarah O’Leary:And so when we bring the two companies together, what we are able to do is accelerate that vision of how do we create a really comprehensive connected product suite that services this full experience of postpartum. How long in advance was that in the works? Because it seems like a really huge move and really thoughtful and interesting, but I also feel like those things can be extremely complicated, especially when you're talking about two different countries. So what was that process like? Yeah, it was a long time in the making, more than a year of time that we were sort of circling around these conversations.

44:08Sarah O’Leary:And then it was about a six-month period that it got really serious. And then like every good deal, all kinds of twists and turns. Nothing turns out quite the way that you expect that it will. And this was certainly no different from that. But ultimately, I think what powered both teams through the ups and downs was we really recognized that we had the same core mission at our heart. I think there was this very weird experience, honestly, of kind of getting to know those British counterparts. And it's like, what are they going to be like? And it was like, they're me. They're us. We are so, so similar.

44:44Sarah O’Leary:and we're fueled by this passionate belief that we can do better for women and the world would be better off if we could embark on that project together. So in addition to advocating and developing more affordable versions of your products to improve access, I know that you've also taken on Capitol Hill in this process and advocating for policies that support parents and moms and families, paid family leave, more affordable childcare. What is your view on this part of your job and what are your hopes for the future? Because it's something I personally think about. I think about parental leave as a whole personally, because I feel like if we want equality in the workforce, we also need equality at home.

45:28And if we could look at everyone who goes on a parental journey in the same way, I think it would help with a lot of bias. But I'm curious about what your journey has been like with the policy side of things.

45:41Sarah O’Leary:You know, I really see it in some sense as our responsibility. I think back to the months right after having a baby, and the whole system is not right. It is like, it is not okay. But I didn't have the energy to fight for myself politically at that time. You what am I going to do? Like call up my congressperson while I'm sitting in a puddle of tears trying to get my baby to latch. Like it's just not a time in life where you're enabled to try to advocate for your own change. And I think in so many ways, women almost just assume that they're the problem, like the system isn't the problem. It's me, I'm failing.

46:16Sarah O’Leary:And so I really, from a deep personal perspective, think that when we have a platform like we do, when we have a brand that is built on making this world a little better for women at this stage of life. It's our responsibility to kind of take that to other areas where we can make impact. And so we have partnered with Chamber of Mothers, which is an amazing bipartisan organization advocating for paid family leave, affordable childcare, and maternal health, and have brought our voice to various forums in DC in partnership with them to essentially, you know, kind of fight that fight on behalf of all the moms that we are trying to make this experience a little bit better for.

46:58Sarah O’Leary:It's hard to answer kind of what I hope to happen or expect to happen because these are big systemic challenges. But I do have this kind of, maybe it's naive or maybe it's hopeful belief that things can start to change when we bring those voices out strongly. You know, I think there's this model of motherhood, which you can sort of see it as like, you know, even what I just said, I'm in a puddle of tears. But it's also like, I just birthed a baby. I am like elemental. I am strong. Like there's this kind of fundamental strength in women's experience and what they've done and what I think that collective power can do.

47:38Sarah O’Leary:And that's really the kind of voice that I'm hoping that we can bring forward and to sort of change that conversation from one of just purely about vulnerability to one of strength and kind of demanding better for our lives, for our kids and for our families. There are few fiercer advocates than moms, right? Yeah, exactly. So it's like, how do we help give voice to where that advocacy can actually create changes in our system? Well, I appreciate it. So one of the things that we like to talk about on this podcast is mistakes because we all make them, but we don't always talk about them. We tend to give the highlight Instagram reel, but I think it's important to discuss it one, because it shows resiliency and that you can screw up and come back from it.

48:24And two, I just think it's fundamentally optimistic to be like, yeah, I made a mistake and look where I am today. You can still sail through, you can still thrive. So I'm hoping that you can tell me about a mistake that you've made at any point in your career and what you've learned from it.

48:39Sarah O’Leary:You're always navigating something you've never done. Let's just go back to like the COVID era, right? It's like, okay, we're faced with this challenge where supply chain for component parts is blocked because of COVID shutdowns in China. And we need to get these parts to this other location. And the only way to do it is to air freight units, and it's going to cost XYZ. Nobody's ever done that before. How do you even know what's a mistake and what's not, right? And so, you know, I think really, it's almost like reframing that to say, you're going to get things wrong. That doesn't mean there are like mistakes or errors.

49:17Sarah O’Leary:They're just, you learned something different later that you made a decision that you wouldn't make again. The way I really think about it is like, just don't make the same mistake twice, figure out what you would have done differently, why you did it the way you did it, not to apologize or justify it, but just like, so you really understand it. Because I truly feel like I'll decide something today and I'm sure it'll be a mistake. There'll be something that's a mistake, but I don't know that I'd frame them as mistakes because everything is always a unique situation. I don't know how to navigate that except with sort of a learning mindset and the grace to not just beat yourself up when you've done something that you wish you could have done differently and you have to move on.

49:59So a lot of the folks who listen to this podcast are in their first lives and they know that they want to make a change, whether they want to stay in their same industry and do a different aspect of it, or they want to change companies or they want to start something, but they're scared. They're nervous about making a big leap. As someone who has pivoted in her career, what advice would you give someone who's standing there thinking about it, but just hasn't made the leap quite yet?

50:25Sarah O’Leary:I think one is, and this was really the clarifying kind of personal experience I had when I became a mom, is you kind of only have one life. You're spending a lot of time at work and make sure that time is putting you in a direction you want to go. And that doesn't mean that every single day is like your favorite day ever, right? I mean, it's still work, but how do you be honest with yourself that being fulfilled and being engaged is a better way to spend your time than feeling like you're treading water? That's definitely been a lens that has helped me know when it's time to take a leap. I've never regretted learning something new.

51:01Sarah O’Leary:Like I've never regretted challenging myself, taking on a new challenge compared to that feeling of just kind of staying in place. And then I think the other thing I would say is I talk to people a lot who are like, want to make this change or sort of really think about things as a pivot. And I think sometimes we almost overdo the language around how much something is a change. You know, when I take a step back from my career, I've had a lot of what people would describe as second lives, pivots, you know, things that are very different. But depending on how I defined what I was doing, if I defined it broadly enough, it all made sense, right?

51:37Sarah O’Leary:So, you know, moving over to Willow, yes, I left consumer and I moved into, you know, med tech and I left a more established brand and I moved into a startup. But I was like, well, I know how to run a website. And I just had a baby. I know what to do here. And I think this is going to be a space that I can grow and thrive in. And so I think in some sense, it's like figuring out where those big areas are that make sense to you, where you have something to add. And it becomes less of a feeling like you've completely dropped everything you knew. And it's this huge pivot and more of a building. And I think that's helped me sort of connect those dots.

52:12It's just an evolution. So my last question is also my favorite, which is if you could get in the time machine and go back and speak to your younger self and give your younger self some advice, what would you say?

52:26Sarah O’Leary:When I was in business school, I took a class called interpersonal relations, which is very famous at Stanford. It's also known as touchy feely, which basically is like a feedback session where people just tell you how you're coming across versus how you think you're coming across. It's kind of as brutal as it sounds, but this incredible learning experience of kind of how do other people see you and how does that marry with your vision of yourself? And we had this closing feedback session. I had a classmate who basically challenged me and said, I worry that you're not going to dream as big as you could, that you're sort of not going to lean in in the places that you could.

53:04Sarah O’Leary:And I think you can do that. And I want you to think about that. And I remember the timing in business school, like, what's she talking about? That's kind of almost insulting. Like, I don't know. It just feels like a little bit. To accuse you of being self-limiting while you're investing in yourself. Yeah. Like what? Where's that coming from? Right. But it has kind of nagged at me throughout my career. And I would say that even when you ask, you know, did you want to be a CEO? I was like, no, I didn't have that on my checkbox. Like, no, not something I wanted. But there's this sense of self limitation that you sort of, I don't know if it comes from fear or just almost like humility or what it is, but this idea that when you say yes to those big opportunities, and when you really look around at the world and say, something's broken, and I think it needs to be fixed, like be the person who fixes it, you know?

53:48Sarah O’Leary:And I think this idea of really owning the impact that you can have and not settling to just kind of go through the motions or the career ladder and not doubting that you can actually be a catalyst and make change. And I think it's really something that I've reflected on sort of in the last two years is like, I can do this. And I can do this in a way that has an ambition beyond even where my company is today. like let's roll up our sleeves and get to work and actually go to Washington, advocate for the things that we think should be better. And you're not going to win them all, but you don't get a chance to change the things you don't try to fix.

54:25I appreciate that tremendously. Thank you so much for your time today, for building such an incredible company, for advocating. I can't tell you how much I appreciate it and how much I've enjoyed spending this time together today. So thank you. Thank you so much.

54:43Sarah O’Leary:This is such a fun conversation. I really, really appreciate the opportunity.

55:13or wherever you get your podcasts. And don't forget to rate and review us. We love seeing you spread the word on social. And now you can tag us in your posts. We are at second life pod on Instagram, Twitter, and Facebook. We always want to know who you're interested in hearing from on the show. So send in your requests to hello at second life pod.com, or you can DM us on Instagram. I'm at Hillary Kerr. The show is at second life pod. Our DMs are always open. I'm Hilary Kerr, and you've been listening to Second Life. This episode was produced by Hilary Kerr, Summer Hammeris, and Natalie Thurman.

55:53Our production assistant is Raven Yamamoto. Our editor is Natalia Perez. Our audio engineers are at Treehouse Recording in Los Angeles, California, and our music is by Jonathan Leahy.

56:11Thank you.

From the publisher

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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