Jennifer Hyman on navigating the move from Rent the Runway founder to Babylist CEO

Jennifer Hyman spent 18 years learning how to lead Rent the Runway through vastly different versions of itself.

As co-founder and CEO, she built a market for something that didn’t yet exist and scaled the business. When Covid brought demand to a halt, she shifted from a growth-oriented, peacetime CEO to a wartime one focused on survival. The experience taught her that leading a company isn’t about sticking to one playbook—it’s about changing with the company around you.

The journey is informing her next chapter at Babylist. According to founder Natalie Gordon, the registry platform serves 40% of first-time parents, helping them prepare for a major new stage in their lives. Hyman joined Babylist’s board in January, giving Gordon a chance to see her leadership style up close.

Gordon saw Hyman in action at board meetings, answering tough questions, building relationships with the team, and identifying underlying problems in real time. In July, Babylist officially named Hyman as the company’s new CEO, and Gordon became its executive chair.

“If you are going to be a great leader, you have to be open to changing yourself. You have to go through the act of rehiring yourself every year,” Hyman told Founder Brew.

Now, after 18 years at Rent the Runway, Hyman is bringing that mindset to Babylist—and taking on a new kind of leadership challenge: stepping into a company that someone else built.

This interview has been edited for length and clarity.

You spent years building Rent the Runway from the ground up. What made you interested in leading Babylist rather than starting another company of your own?

I had the privilege about a year ago of joining the board of Babylist, and since then I was really learning about this new space, this new problem that existed for parents.

I learned about the trust Babylist had built with millions of parents and all the innovation happening there. When I joined the board, there was no thought that I may go over and lead this company. But my journey with Rent the Runway was, in my mind, a complete journey. It was 18 years. There was something to me about that time period—it’s the life of birthing and raising a child until they’re independent. Rent the Runway was my first child, so I had been thinking for a long time about that being a great time to set Rent the Runway out into the universe to exist on its own and continue to grow independently. It happened to coincide with the new energy I was getting from being on the board of Babylist—able to dream again and start to think creatively about a new space.

When Natalie, the founder of Babylist, approached me about considering moving from the board into interviewing for the CEO role, it felt pretty natural. I was experienced with not only the problem and the opportunity of Babylist, but also this incredible culture she had built.

What did Babylist founder Natalie Gordon ask you when evaluating you as her next CEO?

Culture is incredibly important to Natalie, and talent is really the thing that has distinguished this company…As opposed to asking me questions, Natalie got the ability to see who I am authentically by nature of me joining the board, seeing how I was responding to different questions that she had, how I would build relationships with people on her team, how I was contributing to those conversations. It was a really organic way to build a relationship. We both respected each other’s intelligence. We respected the way that we treat other people and that we treat our team fundamentally. You’re nothing without a great team.

We respected the fact that we had been living parallel lives for the last decade and a half. It’s very rare to dedicate over 15 years to founding and then building something from infancy to a scaled organization, and that’s what we both had been through—all of the ups and downs of doing that.

Did you have to unlearn anything when you joined Babylist?

I’m not unlearning anything about being a founder. Being a founder is the best part about my leadership style, and that is actually what I’m bringing to Babylist.

One of the most interesting things about this transition is often a founder will step up into an exec chair role at their company, and they will bring in a CEO who has never founded another company, and so they’re bringing in kind of an operator. This is one of the rare founder-to-founder transitions, and it allows me to continue a culture of entrepreneurship and empowerment that I built at Rent the Runway and that Natalie simultaneously built at Babylist.

Founders are very similar. There’s an aspect of us that are crazy. You’ve got to be a little bit crazy to see a vision for a world that doesn’t yet exist and, without real evidence, go out and do it, and convince and inspire hundreds, if not thousands, of people to join your team and help you build.

Founders are this unique kind of species that is able both to be this strategic CEO and leader, but also understands that everyone has to exist in the work. We have to be at the one-foot level of the organization, really understanding how it works. Nothing is beneath you, that you can be involved in the day-to-day decision-making of the company…I can’t even imagine myself going into a company that wasn’t a founder-driven company.

How are you earning the trust of Babylist’s existing team?

Building trust takes years. I don’t think that you can come in with a playbook and build trust over 30 to 90 days of an onboarding period. People have to experience you through your actions over time and how you treat them. I understand that this is a long game.

I’m building relationships with everyone, not just with my direct reports, and so what I have decided to do is fully immerse myself in the team and the people. Even though the company is remote, we’ve spent the last month, and we’re going to spend the next few months gathering people together, spending time in person, seeing them both in meetings, but then having dinners, having conversations, understanding where their career has been, where they want to take their careers, and showing them through my own actions that I’m here as a partner. I really believe the trust needs to be earned. I don’t deserve that just because I’m coming in as CEO and just because I had this great career beforehand. This is a new environment, so everyone is turning the page.

When you found a company and you are an innovator, there is this assumption from everyone who comes to work for you that you are this brilliant, innovative, disruptive, smart thinker. When you join a new company as CEO, no one’s necessarily giving you the benefit of the doubt. They’re still evaluating: Is Jenn intelligent? Is she going to understand our business? Is she going to be additive? Whereas you’re given a lot of benefit of the doubt at the company you have founded, a new CEO has to earn that level of trust, and you learn it by nature of being in the work with people. You’re not just going to learn it by BS-ing in a one-on-one. You’re going to learn it by digging into a specific problem that the company is having right now and doing the work at the ground-foot level with your teammates.

What’s one Rent the Runway experience you’re bringing into this new chapter?

If you are going to be a great leader, you have to be open to changing yourself. You have to go through the act of rehiring yourself every year, and so that’s about figuring out: A. Do you want to continue to do this and invest 110% of your heart and mindshare into this opportunity? B. How has the company changed around you so that your skills have to up-level themselves? How do you up-level yourself as your environment has changed as the talent around you has changed? People that are open to change are often the most humble people, because they are asking themselves questions of: How could I get better? How can I improve?

A specific instance where I had to change how I lead is when Covid hit, and there was this huge macro circumstance that drove demand way down for Rent the Runway. When we were all sheltered at home, no one was really focused on renting their wardrobes for their events or their office life. People weren’t even going to offices for years, and I had to figure out how to transition from being a growth and peacetime CEO to becoming a wartime CEO and being in the mode of survival, where every single day I was confronted with hundreds of different decisions I needed to make, where those were really life-and-death decisions for the company.

In becoming a wartime CEO, you learn about urgency in a new way. You learn about your P&L and your cost structure in a new way. You no longer are just the CEO. You have to act like you’re the CFO. You’re thinking about every expense line. You’re always asking yourself, “Do I really need to green-light this new initiative right now? Can it wait for later? Learning not only how to grow, but learning how to pause and how to be thoughtful about expenses, and how to question whether what you thought in the headier times was a good org structure or a good P&L.

Coming into Babylist with the experience of having been a growth peacetime CEO for a very long period of time, a wartime CEO for several years, you come in with the mix of being able to respond to any given situation externally, being really thoughtful about the competition and how it’s changing…always having the anxiety that you may be in a great place right now, but let’s think through worst-case scenarios. It’s really healthy as a CEO of a business that’s doing extremely well right now, like Babylist, to have some underlying anxiety around what are the things that could potentially go wrong, and let’s boost up our reserves and let’s embolden all of our moats so that we are able to care for whatever macro situation might happen, whatever could potentially go wrong.

What should a prospective CEO ask a founder or leadership team before accepting the job?

No. 1 is you learn a lot about a CEO or founder by nature of understanding the types of people that they’ve worked with for long periods of time. I didn’t ask to do this, but part of my onboarding on to the board of Babylist was that I met over 30 people. I was able to understand the pattern recognition of what Natalie considers A+ talent, and I could see that we had a very similar point of view on talent. If you are off with your partner or your boss, in terms of what greatness looks like, that’s going to be a recipe for disaster…You need to experience that you have similar points of view on talent.

No. 2: How has this other person led their organization? There’s so many different kinds of management styles, and there’s no right or wrong, but my management style is very founder mode. I don’t care [about] the scale of Babylist—even when we’re generating $50 billion in the future, I will still be at the strategic level and at the one-foot level and be elevating my altitude based on what the company needs. I’m going to be someone who is instilling a culture of entrepreneurship and ownership in the organization. I do not believe that seniority means that you’re off the hook or that you’re just delegating your knowledge of what’s going on in the weeds. Finding that and seeing that mirrored in Natalie was critical to me.

If you go into an organization where the CEO has four assistants and they’re really high level, and they don’t understand what’s going on in the org. There’s lots of great companies that run that way, where people view that their jobs are to just hire people and walk away. That’s not been what Natalie’s done, and that’s certainly not how I run an organization either. Seeing that mirroring of leadership style is critical.

The third thing is just culture. What is the culture of your organization, and is it similar or different to the one where you’re happiest? When I found I was experiencing the culture of Babylist to be very similar to the culture of Rent the Runway, that was another very positive sign for me.

What advice would you give a founder struggling to give up control to an outside CEO?

The first part of the journey is figuring out what your internal priority and desire is. When it came to myself and Rent the Runway, I was so obsessed—I am still so obsessed with Rent the Runway…I knew that in order for me to take on and start a new chapter, I would actually have to close the last one, because I was so attached to it that I can’t be one foot in, one foot out. I wanted to give myself the freedom to dream again in a completely new space and immerse myself in something new.

Natalie’s approach is different, where she did her own soul-searching and realized she didn’t want to be in the CEO role anymore and actually conducted quite a lengthy search before even approaching me related to this role.

What’s the best money you’ve ever spent as a founder?

My best money [spent] is on some of the key people that I hired. I spent a lot of money early on on what some people thought was an overhire, where you bring in someone amazing and they cost more money, especially based on the stage of where you’re at. But I knew in my gut that these people would be transformative to the organization, and they were.

You never regret investing in talent, especially because it’s a no-fail problem. You invest in talent, you give them great equity, you give them great compensation, and if they don’t work out, they leave, and you’re not paying that compensation anymore.

Everyone has to have skin in the game. Be very generous with the equity that people receive in this organization so that people are true owners.