Carolyn Childers – Co-founder & CEO of Chief

Kara Goldin 0:00
I am unwilling to give up that I will start over from scratch as many times as it takes to get where I want to be, I want to just make sure you will get knocked down. But just make sure you don’t get knocked down knocked out. So your only choice should be go focus on what you can control control control. Hi, everyone, and welcome to the Kara Goldin show, though, join me each week for inspiring conversations with some of the world’s greatest leaders. We’ll talk with founders, entrepreneurs, CEOs, and really some of the most interesting people of our time. Can’t wait to get started. Let’s go. Let’s go. Hi, everyone, it’s Kara Goldin from the Kara Goldin show. And I’m so excited to have our next guest. We have Carolyn child ers, who is the co founder and CEO of chief and chief has just come onto the market over the last couple of years, I feel like and really, really exciting. I’ve read up on Carolyn and and, you know, other co founder as well, that it’s just been, it’s been great to kind of hear how a leader and an operator can successfully scale especially during these crazy times in early stage business. Prior to co founding chief Carolyn was the Senior Vice President of Operations at a company called handy and previously led the launch of the site soap.com, all amazing brands that you’ve worked on. And then there’s one other little brands that she worked with where she became a GM at Amazon, so had an amazing experience along the way. And she for those of you who are not familiar is a private network designed for female executive leaders to strengthen their leadership, while paving the way to bring in others as well. So we’ll hear a lot more about that from Carolyn, but I just want to welcome you. Thanks for coming on.

Carolyn Childers 2:12
Thank you. I’m thrilled to be here. I have been a huge fan of you’re so excited to have this conversation and just hopefully have a have a good chat.

Kara Goldin 2:23
That’s incredible. Well, thank you for the very nice and kind words, I really appreciate that. So let’s go back to where it started. So you started your career I read in finance. And so you were shifting into strategy and business development. So talk to me, we have a lot of people who are just thinking about their career, a lot of people who have maybe just started their career or college students who are listening to this podcast as well. So how did you think about your career? I guess, when you were first getting started? And how did you start to think about transitioning as well?

Carolyn Childers 3:00
Yeah, absolutely. I kind of wish it was as thought out as some people’s careers are. It’s funny, I never would have thought that I’d be an entrepreneur at this point. In my, in my life. I, I think you hear these stories all the time of people who from the very young age had just this entrepreneurial, entrepreneurial spirit of like a lemonade stand. And all of these, like businesses that they were running, when they were very young. And for me, my family, my mom’s family, in particular had their own business. And it always just felt like this really intense endeavor to kind of be, you know, their own business, their business owner. And so I actually, when I went into my career was like, you know, I’m going to go into big stable company, I’m going to, you know, get some really great learnings out of the gate. And, you know, finance seems like a very good stable, like, right place to be. And so that was kind of how I went into my career was where can I learn most what is like a good, great trajectory for, you know, what I want to be over time. And then I really quickly realized how much I was craving actually being able to build and to, you know, be the operator behind something instead of crunching the numbers and finance. So it wasn’t the right place for me. But I think there was some family legacy in the early days that kind of made me think, didn’t even consider going into the entrepreneurial side of things for a long time.

Kara Goldin 4:39
That’s so interesting. And so you How did you get to how did you get to Handy was handy. That was that was further down the line? Right? So

Carolyn Childers 4:49
I was further down the line. Yeah. So I started my career in finance, investment banking. I did that for several years and then moved over into the corporate side. I worked for a few big companies, Avon and Victoria’s Secret. And after I went back to business school, I still came out thinking, you know, big company that’s, you know where I want to be. And a good friend of mine from business school had actually gone over to Quincy, which was a parent company of diapers and soap. And it was just diapers at that point. And he actually called me and said, we’re looking for somebody to come in and launch so. And so I went and met with Mark Laurie, who I’m sure people may recognize the name, he was the founder of Quincy, went on to found jet comm and met with him and his co founder Vinnie. And I’m still not quite sure why they hired me because I had no ecommerce experience. I think I had managed maybe two people in my career, I’ve never been at a startup. But there was something in me that they really liked. And they brought me on to launch and run soak calm, which, you know, we grew to over 100 million, and then it got acquired by Amazon. And as soon as I made that switch over to startups, there was kind of no going back to me. For me, it was the place that I wanted to be. And that kind of continued the journey of multiple startups, actually went over to South Korea for a bit and worked on a company called coupon, which is now the Amazon of South Korea, wow. I, and then went to handy and worked there for several years before finally saying, Alright, it’s time for me to go and launch, launch a business myself, and brought me to Chief.

Kara Goldin 6:34
So you were so you worked in finance, you worked in strategy, and then at handy, you were the senior vice president in operations. So dealing with this supply chain, and right, well, handy, actually different type of, you know, issues probably there versus what you were doing it so clearly, but what, what were some of the differences that you saw, I guess in in, I mean, you went from physical goods, right to more of services. And and so what what were some of the big things like differences, challenges, obviously not touching physical goods and some way but was it easier or harder? Or what were sort of some of the trade offs?

Carolyn Childers 7:17
Yeah, I mean, I think one of the biggest things that I discovered, you went from more of an E commerce business, which there’s just more of the elements of that experience, that are in your control, you know, the every step of that journey, from the time that somebody orders all the way through to when you know, the packages is being delivered, you are able to control so much more of that experience versus marketplace service businesses like Handi, where you have, you know, home services that are happening through a professional network that is 1000s of people. So how do you actually build consistency, operationally, in a marketplace business like that, that is a really hard thing to tackle. So it was very interesting going from, you know, a model, like Quinsey, which, you know, a lot of what you were focused on was more around, how do you increase frequency of purchases? And how do you make the unit economics work and all of those types of questions that are kind of prevalent in a lower margin e commerce experience to then go into a marketplace that is very experiences joint focused, and really the thing there is, people will repeat, it’s not about you know, that side of it like it is on E commerce, if the experience is great, but how do you actually consistently deliver an experience so was really interesting to see both of those different business models. And I truly do and would encourage anybody to just have that like intellectual curiosity to go and really dive into all of these different business models that on the surface, some of them might look really easy. Oh, that seems like a great business. And then you dive in, you’re like, Oh, this is incredibly complex. And here are the different challenges. It’s been really fun to be able to do that across a number of different businesses in my career.

Kara Goldin 9:11
Yeah, definitely. I that’s what I picked up on in your experience, that it wasn’t just about growing and understanding different departments, but also just this whole idea of shifting from from services, physical goods into services. So I did services to physical goods. And so it’s definitely a little more challenging, I think, with the physical goods, but not necessarily. I mean, I think that they both have pluses and minuses for sure. And sort of how you’re evaluating things and certainly today, I think, you know, the direct to consumer world of iOS and all the challenges there and and for sure, I think it’s a you know, there’s there’s lots of tough things In all of those different types of businesses, but let’s get on to the most important, most inspiring of your career is founding chief. So where did this idea come from?

Carolyn Childers 10:14
I think most good startups come from a place of really personal need. And that was very true for me for Chief of I was getting more senior in my career. And I just felt like I was no longer really investing in myself as a leader, I didn’t feel like I actually had a community to turn to when there were these big challenges that were ahead of me and a good sounding board to be able to talk through some of that. And, you know, I think the saying is very true of it gets lonely at the top. And I think it gets lonely or a lot earlier for women, because you are often the only person in the room, the only woman in the room. And so that was kind of the inspiration for me was, how do you actually create a great community and network of women that can come together, and not just meet over wine and have casual conversations, but actually can be a real support network for each other, and achieve one of the things the primary things that we do. All of our members, we break it down into groups of 10 women that meet on a monthly basis, there’s an executive coach in the room. And it’s just this amazing way for you to truly be able to help each other work through your biggest professional and personal challenges, which is just space that I think we all really should give ourselves to be able to like have that community to turn to, instead of trying to muscle our way through it on our own.

Kara Goldin 11:48
That’s awesome. And so was the original business plan you started in January 2019. Was the original business plan physical locations, or what was what was kind of the thinking behind that.

Carolyn Childers 12:03
So I think our our intention had always been that at some point, no matter where you were in the world, you’d be able to tap into the power of the chief network. We were kind of inspired by the peloton model where it started in a studio in New York, and there were classes but now you can you know, participate and be a part of that community no matter where you are. So we started it a in a physical location, we actually had a clubhouse down in Tribeca in New York. And the value of the community is it. And what we often say is we were a community that happened to have a clubhouse, not a clubhouse that then tried to build a community within it, because the majority of people would come to that space for these what we call core group meetings, this peer group model, they be coming for that not to use the space as a co working space. So it started in a in person way. But it was almost more of like the format was through the clubhouse rather than the actual value was the clubhouse. And obviously, over time, particularly with a pandemic that has shifted, where now most people are able to participate in everything achieve without having to schlep across a city to go to a physical location.

Kara Goldin 13:29
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Carolyn Childers 16:40
I think the pandemic obviously forced upon us a pivot in our model of moving from what was happening in person to virtual. And what was amazing to us was that engagement actually went up. So we had more people participating in all of the services that we were that we were providing, as we were doing it through our virtual format versus in person format. edits, not too surprising, given you know, you’re the beginning of a pandemic, when there’s truly no playbook for how to be a leader. This is the time that Chief has actually made for to be able to, you know, tap into the other women that are a part of this network and figure out how people are handling this as leaders within their companies, but also at home, because now you were homeschooling, how are people handling this and navigating all of that. So it was amazing to see that, even with this new format. And in this new format, it was actually expanding the value that we were able to give to people and the amount that people were able to engage in it on a monthly basis, versus just every few times that they actually came into the physical space. So I think it unlocked a lot for us, I would say that, we still have clubhouses, we have one in New York, we have one in Chicago, we have one in LA, and they’re still a great part of the experience, I kind of view them as kind of the cherry on top of you have just this amazing, robust experience that you can tap into anywhere. But you can also, you know, go grab a drink at one of the club houses, if you’re in town, or if it’s in your city. And it’s not the main crux of what we do. But it’s a really nice extra benefit to be able to have access to and to have access to all of them.

Kara Goldin 18:35
That’s awesome. I totally agree. I think it’s it’s become a I think more and more people want kind of the smaller groups to have getting together. So I think that that’s, we were at a place a few years ago, where everything was open right now people I think, want some sort of smaller spaces in some way to be able to get together with people. So there aren’t too many people to and inside of a venue. So, so interesting. So your programming in 2020. I read, included, you know, all kinds of workshops and topics like digital disruption, what what is kind of the most popular thing like why do people want to have these? These get togethers? I mean, what is sort of the number one thing that people are trying to get through more than anything? Yeah,

Carolyn Childers 19:29
I mean, I think that the most common thing that you often hear when we bring people together in these groups, and they’re kind of working through their biggest challenges, we actually really intentionally don’t put people together that are from the same function because we don’t want people to come in and be like, what are the best marketing tactics that you’re deploying right now and how are you using Facebook these days? And and instead, it actually really goes to like you as a leader, and most challenges ultimately are people challenges At the end of the day, as a leader, and so all of the conversation really revolves around that of, you know, how do I think through the team that I’m building, the strategies I’m putting together, like, those are the types of things that you’re really starting to talk about. And then it just gets a lot deeper of the challenges that you’re that you’re experiencing some of the full network programming, which I think you were referring to, like, that’s kind of what I was mentioning before. It’s kind of the content of what happens. Yeah, core group, that small group, the broader network, I think, one of the great things is, yeah, there’s some great tactical learning you can have. And we’ve brought in, you know, professors from some of the best business schools and exec ed programs, and so you get to tap into that. But you also just get to tap into really inspiring leaders that you can learn a ton from, I think it’s similar to what you have tried, what you are creating in this in this podcast. We have Michelle Obama coming next week, to talk to the community, which is amazing. And, you know, I think just being able to listen to hear from and get inspiration from leaders that are paving the way is a great thing to remind ourselves of,

Kara Goldin 21:22
no, that’s absolutely great. So I read Amal Clooney came on or came, I mean, all of these amazing, amazing people, which I think is just an incredible place to be able to hear them talk about the challenges that they’ve come across, too. So tell me a story. When building chief were you faced a big challenge, or failure, and it could be a chief, it could also be at one of your previous roles where you definitely, it was hard, you didn’t know how you were going to get through it. But you learned so much from that experience. So share a little bit more about that.

Carolyn Childers 22:03
I think everybody should have a very recent example to be able to give if you were a leader over the last two years, I think the pandemic really tested everyone as leaders. So I mentioned before, you know, Chief had a very in personal experience. Everything was happening in the physical space in a club house in New York City. And we had actually just raised our Series A, we had just raised some capital, with the idea of starting to go into new cities, we were going to expand from New York and go to LA and go to Chicago. And we were kind of on the precipice of that expansion. We had just signed leases for new spaces. We were starting that expansion story when the pandemic hit. We had had like the today’s show had come in in January and had done a whole segment on us. And like, the irony is that it it aired the exact day when everything went into lockdown. It’s like the, you know, a great moment to celebrate at the exact same time as you’re like, do we have a business anymore? I’m not sure because everything was happening in worse. So as this really weird irony of like, we feel like we should be celebrating. But we need to make sure that this business sustains through this. And I think that we were at the very top of every one of our investors lists of all right, who should we who are we worried about who’s going to come out of this. And I just give incredible credit to our team of how quickly they not only took all of our existing services, and like worked, and we moved it over to virtual, I don’t think we missed a single week of coordinating meetings, like we were able to move them all over, we were able to train all of our facilitators of those sessions. We had all of the logistics down for that to actually be a virtual experience without missing a week. Similarly, with all of our other programming moved in all over. And on top of that, we actually invested in additional experiences for our members to make sure that they were supported as much as possible through what was arguably probably one of the hardest times for them as well. So we added in one on one coaching if you wanted to be able to have sessions directly with some of the coaches on our platform. We added a hiring board knowing that so many people were furloughing on their team or being furloughed and just really wanted to invest in those experiences. But it was some really dark days of in the early parts of it of just how do you as a leader really speak with clarity and some insincerity while also knowing that like there’s some real questions and real asks that you have to make of your team? And how do you galvanize the group to really work through a very unknown time as a business?

Kara Goldin 25:12
Yeah, definitely. And I think that that’s, that’s something that even when you work for some incredible entrepreneurs, either directly or indirectly, from your other experiences, I don’t think you really understand that when you go and start your own company, right? It’s it’s a, I mean, it really, it certainly is kind of this this place where you can talk to other people, you can, that’s where chief I think comes in amazingly great. People who are leading who people who are going through it like you are, but when you’re supporting another entrepreneur, it’s just don’t you agree? Like you don’t really understand how lonely it is, and in many ways, and and how challenging it is, I always talk about entrepreneurism as somebody handed you a puzzle, and you’re like, I can do puzzles, I’m awesome at doing puzzles, but they don’t hand you the picture. Right? And, and then yeah, you know, you go along the way, and then they said, Oh, by the way, some of those puzzle pieces didn’t belong to you, we’re gonna take them away. And then they throw more back to you over time, and then they say, Oh, we didn’t tell you it was supposed to be two different puzzles. I mean, this is this is it, and no one ever hands you the picture. Right? And, and at the end of the day, that’s, that’s you, as the CEO, as the founder who’s trying to figure a lot of stuff out, and, you know, and make payroll and everything else along, it’s hard. It’s, it’s tough.

Carolyn Childers 26:54
The thing that I have found is that, you know, I’m a fairly strategic person. And so like, as an executive at so many other startups, I would just kind of be like, Okay, well, strategically, here’s what makes sense, or does it make sense, and it was just so much easier to have a pure strategic lens, instead of the emotion that comes with being the entrepreneur of like, this is your team, this is your culture, this is your, there’s so many things that just feel so much more personal, when it is a direct reflection of you in the company that you want to build. And so it doesn’t become strategy anymore, it just becomes so much more personal. And the, you know, moments like the beginning of the pandemic, where you’re trying to pivot the business, but you’re also just like, really wanting to make sure that your team is okay, because they are also going through a big change and full of uncertainty. And so, you know, I think the things that I learned most going through it is that you can’t communicate enough, like the amount of communication has to double and triple over that time. And they kind of have to put the max oxygen mask on first for your team, and just make sure that they are good and their sound, and they understand where your direction is headed. And, you know, I’ve I’ve been a athlete and a team sports my entire life. And you know, I love the team dynamic. And I think that really put this team to the test. And it’s just so proud of what they were able to do over that time.

Kara Goldin 28:28
That’s incredible. Where are you based, by the way

Carolyn Childers 28:31
we are based in New York. So that is that is our headquarters, I’m not going to deny that I’m actively sitting in Florida avoiding the New York winter right now.

Kara Goldin 28:42
That’s fine. And many people have transplanted down to Florida as well. So it’s so interesting. So how do you balance that strategy? What you were just describing between, you know, the emotional side of being a leader. And I mean, that I think the emotional side also, I don’t know, I go back and forth even on culture, because I think culture sort of crosses between, I don’t know where it sits, it sits in it is a part of, I think, a strategy but it also is an emotion and a feeling the heart and soul of a business too. But how do you have like, how do you balance that?

Carolyn Childers 29:28
I honestly think that more people should tap into the emotion and show that vulnerability and show that sincerity and and I think that people gravitate towards that. So I and I and I think there’s a big movement in leadership of of having more of that side too. So I I hope more people I think if anything, people are too balanced to the strategy and not as balanced to the you know, The willingness to show the human side and the humanity of it. So it’s something that’s, you know, I don’t think I learned early in my career, especially starting in bigger companies where it’s just like, no emotion, no emotion allowed. But I do think that people are really starting to see the benefits that come with deeply investing in those relationships, showing vulnerability showing that sincerity. And, you know, the all of the research that has come out now of just how much deeper that builds trust within an organization, I think is is wonderful.

Kara Goldin 30:40
Totally agree. Well, this is been an amazing, I mean, it’s so educational, and I’m so excited for chief in the future. And so needed, I think, more and more people are really feeling like they need to find their people, right and find people who really understand whether it’s within CI for you know, your own networks, I think that that’s something that is so top of mind for people and to get through kind of sticky, challenging times, but also times that are new for people that they just don’t have kind of the experience to be able to go through it. So I’m very, very excited that you guys exist. So really, really great. And how do people find out more about chief? I know you have a wait list? That is pretty extensive. But definitely, how do you how do you find out more and and what are kind of the qualifications for it as well?

Carolyn Childers 31:39
Yeah, so you can go to Chief comm and apply to be a member. There, there is a waitlist, but we are working through it. So I definitely encourage people to come and apply. And we do focus on senior executive women, I think the personal story for me was the loneliness of being in that senior executive position. And when you are a part of a broader network, you also often become the mentor instead of finding that community that you yourself can continue to invest in yourself as a leader. So we do try to really focus in on VP level and above women so that we can ensure that we bring together people that have similar challenges and contacts. So that’s kind of the qualification that we think about and we’ve just excitingly fully not launched nationally, we have just been in seven cities up until the end of 2021. And at the beginning of this year, officially launched nationally. So regardless of what city that you were in, we welcome you to go to chiefs calm and apply.

Kara Goldin 32:50
That’s awesome. Well, Carolyn, thank you so much for coming on and speaking with us and sharing so much of your journey and your stories. It’s it’s really, really great to have you and thanks everybody for listening today. Don’t forget to subscribe to the Kara Goldin network and make sure to give this episode lots of stars as well. Carolyn was great and so kindly spend some time with us and give her wisdom. And definitely get the latest from me daily all over social at Kara Goldin with an AI and shameless plug. If you haven’t read my book, undaunted, please pick up a copy or download it on on Audible. It’s really my my own story of building hints, and so much more. And hopefully, you’ll get a chance to let me know what you think. And last but not least, grab a case of hint. And we’re here every Monday and Wednesday. So definitely, come and join us and let us know what you think. So thanks, everyone. Bye for now. Before we sign off, I want to talk to you about fear. People like to talk about fearless leaders. But achieving big goals isn’t about fearlessness. Successful leaders recognize their fears and decide to deal with them head on in order to move forward. This is where my new book undaunted comes in. This book is designed for anyone who wants to succeed in the face of fear, overcome doubts and live a little undaunted. Order your copy today at undaunted, the book calm and learn how to look your doubts and doubters in the eye and achieve your dreams. For a limited time. You’ll also receive a free case of hint water. Do you have a question for me or want to nominate an innovator to spotlight send me a tweet at Kara Goldin and let me know and if you like what you heard, please leave me a review on Apple podcasts. You can also follow along with me on Facebook, Instagram, Twitter and LinkedIn at Kara Goldin. Thanks for listening