Carolyn Childers, co-founder & CEO of Chief

For my latest Tiny CEO interview, I interviewed Carolyn Childers, the co-founder and former CEO of Chief. Chief is a private women's business networking organization for senior executives. 

How did you get your start in business? Did you always know that you wanted to become a CEO?

I started my career in the services business. I was doing investment banking and helping other companies, and I really wanted to be more of an operator myself. I wanted to not just advise other people on how to run their business but actually be able to roll up my sleeves and do it myself. I didn’t think I had the ambitions of being a CEO per se, or starting my own business. My grandparents ran their own business, and I saw how hard that can be. But in the end, I knew I wanted to build and create and be an operator. I started to join startups that were building from scratch, and just loved being in the early stage of a business. Eventually, the idea of Chief came to me and I was like, “This is the time to go and start my business.”

What gave you the idea to co-found Chief, and what is the mission of the company?

Chief is focused on building a community of senior executive women in business. As I got more senior, I was supposed to have all the answers and be able to help everybody else with their challenges. But I still had help that I needed, and I wished that I had a community of people to tap into, to navigate the challenges that come with leadership. That was a personal need that I felt. Then I thought, “Wouldn't this be great to build an actual business around all of this?” That was the inspiration for Chief, and I have been so excited to build it. We now have close to 20,000 members across the whole US. Chief is the essential network that executive women rely on to maximize the impact that they can have in the business world.

How did you meet your co-founder, Lindsey Kaplan?

Lindsey and I met at a networking event for women executives, and it was not the best event. I met Lindsey, which was a huge outcome. But I remember thinking, “I wish that there was something better in the way that we, as women, as executives, could come together and learn.” So we often joke that even a “not great women's networking event” can lead to 2 co-founders finding each other. Imagine if you build a great experience and a great network, and what that could do! I give a lot of credit to all the people who go on the entrepreneurial journey by themselves, because it's really nice to have a co-founder for the highs and the lows, and you're just in it together. I have been incredibly lucky to have a great partner in Lindsay.

I have interviewed Ann Shoket, CEO of The Li.St, and I know there are several other communities for women in business. I was wondering what you think sets Chief apart?

First, I love that there are multiple ways that women can tap into a community. I wish there were more because everybody has their own take on it. And it really allows everyone to find the community that fits them the most, as well as what's most important to them. One of the things that was very important for us as we built Chief was that we wanted to make sure that there were deep, meaningful relationships. So often there are experiences that you have where you see somebody, you meet them at an event, and then you forget who they are. You don't keep in touch with them. We wanted to move past the surface level networking into much deeper relationships. We call that core. It's a group of 10 individuals we create, and Chief has hundreds and thousands of core groups that meet every month with the same 10 people. There's an executive coach in the room, and it opens up this deeper level of authenticity and vulnerability to be able to talk about the real challenges that you have. For us, that was important as we built this: How do you move past networking at large and into really deep relationships?

What is your favorite part of your job?

Well, I am currently out in L.A., at a beautiful hotel, for an event. And why I mentioned that is because I think so often you can, as a CEO or as a leader, you can be in the internal meetings with your team and in spreadsheets and working on strategies. What I love is when I get to actually be in community with our members. At our event tomorrow, all of our members from L.A. are coming together at this hotel. Those are the moments where you remember why you do what you do and how much work it is, and all that you pour into it. It matters so much when you get to interact and see and hug and just be in community together with all of our members.

What is the hardest part of your job?

There are always hard decisions you have to make as a CEO, and you know that some of them will not be the decisions that everybody will like or appreciate. Having those hard conversations, knowing that sometimes it's better to be respected than liked, and knowing that sometimes you're making the best choice out of no great choices. But you're just trying to do the best that you can for your team, for your business, for your community.

Who is your favorite woman role model?

I have my family history. My grandmother was one of 3 girls. My mother was one of 3 girls, and then it's myself and 2 sisters. There are a lot of women in my family. It's heavily matriarchal in the Childers home. I say that partly because my role models are my older sisters. I think that's why I think it's so powerful to have a community of other women, because I had that with my sisters. My older sisters were role models to me the whole way and continue to be the first people that I want to call when I need advice on something. I've deeply respected how they have navigated their lives and careers, and even though I'm only a few years younger, those few years have given me a lot of ability to watch them, to have deep respect for them.

Do you have any advice for young entrepreneurs like me who are looking to start a business?

I love that you are doing this series. One of the things that I wish I did more of as I was building my business was to connect with others who had done it, and to learn from them, and to build the relationships so that you could continue to ask questions as you find yourself at new hurdles within the business. Spending time with people and learning from their journeys, and not doing it alone is incredibly important, to have a community to learn from. I think it's incredibly impressive that you are doing what you are doing right now as you build your business!