Chief: Changing the face of leadership

they're leaving the workforce. I think we all know, and yet we're not doing enough to support women and to really give them strength when they get there. Welcome to Calling Bullshit, the podcast about purpose washing, the gap between what companies say they stand for and what they actually do, and what they would need to change to practice what

they preach. I'm your host, Time Montague, and I've spent over a decade helping companies define what they stand for, their purpose and then help them to use that purpose to drive transformation throughout their business. In this special positive case study, we're headed to Toronto with the leaders of

an extraordinary three year old startup called Chief. I'm going to interview co founders Caroline Childers and Lindsay Kaplan on the main stage at the Collision conference where they're going to tell us how they're pursuing Chief's purpose to change the face of leadership. When you close your eyes and picture of CEO, who do you see? Who I see? Is this girl I knew in high school who started this like shoe company. And then there's like the faceless corporate man in the suit too. But like it's a

bit of vote of course. Like back in the day was like a man um but now I think it's very diverse, getting a lot more diverse. I wouldn't say like a male or female. It's a picture, but the first thing that comes to mind is a man. I see a guy in a suit. Yeah, hot guy in a suit. It does feel like to some extent there's kind of like an ivory tower, you know, there's like an in club, and then that produces the same kind of people. I think that the people that are in

power are pretty homogeneous. It's true, corporate America is homogeneous. In there were more men named James serving as Fortune five CEOs than all the female Fortune five CEOs combined. Last year, the number of women on the list came to a pathetic forty one and in its entire history, only four female CEOs have been black. But what's even crazier, I mean to me at least, is that we now know that diversity at the top leads to better business results.

Because of this, things are finally beginning to change. For example, Goldwyn Sacks won't take a company public unless the leadership team meets their new diversity criteria. But change is painfully slow. When it comes to leadership, women still face pernicious stereotypes.

For instance, they're more likely to be seen as consensus builders, not as aggressive decision makers, so even when they are promoted to CEO, it's often when a company is in crisis, which of course increases the pressure on them to perform and decreases their chances of success. This phenomenon, known as the glass cliff, means women typically stay in power for shorter periods of time than their male counterparts, and when

they leave, they're often succeeded by you guessed it, white men. Clearly, we need more women in power and more support for them when they get there. To solve this problem, Caroline Childers and Lindsay Kaplan founded Chief, a private network designed to give women the tools they need to strengthen their leadership, magnify their influence, and pave the way to bring others with them. Chief helps their members to hone their leadership

skills while also fostering community. Within just three years, Chief has grown to serve more than ten thousand women, and it's attracted speakers like A. Mall Clooney and Michelle Obama. With meeting spaces in three cities, evaluation of a billion dollars and plans for expansion, Chief is on course to truly live out their mission and change the face of leadership. All of our positive episodes focus on industry disruptors, but as an organization looking to disrupt every industry, I knew

the Chief co founders would be amazing guests. We met up at Collision, a big tech conference in Toronto where thirty five thousand attendees learn from the most successful entrepreneurs in the world. Caroline Lindsay and I recorded two conversations there. First, we spoke on the Collision main stage about how Chief supports driven women in their climb to the top and helps keep them there once they arrive. Then we hopped over to the Collision podcast booth to go deeper on

the why. Here's how it all went down. First, I want to welcome you both to Collision and welcome to calling bullshit. Thanks for having us. It's all bullshit. Yeah yeah. So, as you know, on this podcast, we focus on purpose led organizations, some of whom have some issues, but we also since we like to light candles instead of just curse the darkness, we want to focus on purpose led businesses that are really getting it right as well. And obviously you fall into the latter category. The two of

you are absolutely crushing it. So, but I wanted to just start out by getting into a little bit of background. What is the history of Chief? How did the two of you meet? What made you decide to start this business? Yeah? Well, I think the irony is that Lindsay and I first met at a women's networking event. Um, and it wasn't the best one. It was terrible. And we've all been to these networking events with like amount of cheese on the side and warm white wine and named tags that

are placed in awkward positions. And Caroline and I saw each other and enrolled our eyes and it was cynicism at first glance. It's cynicism. That brought us together. But we often say, you know, if a bad networking event could actually bring together to co founders, and I imagine

what a really powerful, well intentioned network can do. Uh. And so as I started to think about the idea of Chief, UH, Lindsay was one of my first calls to start to talk about it as my co founder, and I think for us, the idea of Chief came from a very personal place of we were both getting more senior in our careers. We're spending all of our time managing teams, mentoring people, and actually never felt like

we had resources for ourselves anymore. And that was our inspiration to go and art an organization of Chief, to build the most powerful network of women and really focus on senior executive women as our as our first step, right, And so how do you articulate the mission a Chief? Well, our mission is to change the face of leadership. It's really simple, and yet we have a really big job

in front of us. At the current rate of change, it's going to take over two hundred years for women to reach parity in the workplace, and so we need to make that change now. And it starts with powerful women coming together and creating a ripple effect in their organizations and in their communities as well. I love that. And you know, purpose led businesses tend to be disruptors. I just love to hear you talk a little bit

about the dominant belief system that you are trying to disrupt. Yeah, I mean, I think it's interesting because in some ways it's disruption, but other ways it's building the status quo that has allowed certain types of people to find success where others haven't in just building that same ecosystem for different demographics. Um, And I think we all know that, Uh, A big part of what allows for success and allows for new opportunity is who you know and those networks

that you build. So I think for us it was really important to create a similar type of ecosystem and network that I think has been in place in many ways for certain demographics that just haven't been in there in that in that same shape and form for others. Right. Yeah, I mean some of the doing my homework for this, some of the statistics about women in sea level positions are shocking. Right, less than eight percent of Fortune CEO are female. Of board seats globally are occupied by women,

And the thing about this to me? Is that makes it so crazy? Is I've also seen suggestions. I was reading a McKinsey report that says business outcomes are better in companies where there is diverse and an often female leadership. So it's it's almost like the patriarchy is cutting off its own nose despite its face. You know, if you like, I just don't. It's it seems crazy to me. So, I mean, I would assume vcs here in the audience. I hope, I hope you are listening to this. You

will get better outcomes if you fund diverse companies. So I'd love to hear if either of you have experienced any of the the issues that you're trying to address

through CHIEF personally in your careers. Yeah. I mean, I think for me, the UM the real focus on this area and the drive to start something like Chief was as I started to be in those rooms where decisions were being made and recognizing that it was just different conversations, UM, and it was more affecting my team than me because I didn't hear the conversations about myself, But as I've heard the conversations being had about people on my team

and different ways of evaluating people different ways of even just thinking about problems and not taking like the holistic point of view of recognizing that a business solution that might be great for certain populations aren't great for all populations.

And so I think it was in those moments where you were finally in that room and you saw how it was playing out differently for such different populations, was and it's why we wanted to start with senior executive women to just get more of them into that room and make sure that more of those perspectives were being shared in those rooms. And the ripple effect that that could have across so many different organizations. I love that. So I want to pivot to just talking about the business.

I want to understand how the business actually works. So how how does one become a member of chief? So we are a vetted network, So we, like I said, focus on senior executives, which the easiest way to describe what that is is VP level and above UM. And it's really important for us to make sure we stay vetted because otherwise you end up falling into that de

fecto mentor. And we want to make sure that there is truly a peer organization of people that understand your context and responsibility UM, and it's an annual membership model UM. I think the amazing part of all of this is that companies have recognized some of what you were saying before that there needs to be more representation, They need to be investing in their amazing women talent. And so about seventy of our membership is actually funded by the companies.

In the same way that they would send you to a conference UM or get you an executive coach, they will fund a membership into Chief UM and there's a whole suite of services that you get as part of that membership. The probably dominant thing that we talk about is what we call Core UM. It's called Core for a reason. It's a it's a peer group where we break down the entire community into groups of ten that

meat on a monthly basis. There's an executive coach in the room, and it's just this amazing opportunity for you to work through your biggest professional and personal challenges. And the two of you are in some of these groups, Yeah, you actually participate as absolutely. Shout out to my Core group. We had a great session last week. And look, it's really important for women to find other women who are in these senior levels and have time in a confidential

space to talk about things that are pressing for executives. Right, executive problems always end up being people problems, and it's really important to find a professional board of directors to go through that, to give diversity of thought, opinion advice to help you not only become a better leader, but to stay motivated and to stay a leader and not burn out. So one of the things that I have noticed folks here have probably noticed as well, is that

you've been out raising some money. I think I've got these numbers right. You've raised a hundred and forty million dollars and your latest valuation is one point one billion dollars. Yes, it's a lot of powerful women. But how does how does that first? How does that feel? That's got to feel pretty good? Yeah, I mean, I think for us, we start a chief about three years ago. Um, and if you think back to where we were three years ago,

we started early two thousand nineteen. Then you had the pandemic. There was just so many shifting things that have happened.

And I think for us, this milestone is less about like evaluation and it's less about uh, you know the amount that we raise, and I think it's actually more for us, just a really amazing moment to be able to celebrate a lot of pivots that had to happen over this period of time and the idea that investing in women is good is a good investment decision um and so we're really proud of that and our members are really proud of it, and it's just been an

exciting time. So how are you using that money? Yeah, I mean, I think for us first and foremost, as always, we have fifteen thousand active members right now, we have sixty thousand members that are on our potential members I should say that are on a wait list. So for us, we're just really wanting to make sure that we continue to invest in the experience and build more for all of our all of our members. But we're because we're in such early days of what we can build and

who we can build for. So we're talking before about the fact that you know, our mission is to change the face of leadership. We were really thoughtful about where we wanted to start with senior executive women, but to really change the face of leadership, I think there's so much more that we can do under that umbrella, right, and you have physical locations as well. We do. We always say we're a community that happens to have a space, and so we have spaces in New York, l A, Chicago,

and one on the way in San Francisco. But really what makes Chief special is the network is those core groups that as we know, we're not really reliant on spaces anymore, and so they're wonderful amenities. They're great for getting our members together. But if you're joining, you're joining to grow that network and to be a part of the community. And do you have plans to expand outside

the US. So we just launched nationally in January, so we're still in early days of just being two days in Canada, and I think that's on the road map now. So thank you Toronto. So we will we are working

on expansion. I will say this. When we did raise the money, we knew it was really important for us to think about how we grow and continue to stay diverse, and so we committed to doubling our grant program to making sure that we are welcoming in women from all different areas, from different roles, functions, um as as underfunded women founders, and we're also committing a million dollars annually to make sure that we can invest in nonprofits charities

that are aligned with our mission of changing the face of leadership. One of the things that I have learned from other CEOs of of purpose led businesses, they have pointed out to me that who you raise money from is actually quite important. In other words, having investors who understand your mission, are aligned with it, and I'm really supportive of what you're trying to get done. Has that

been part of your journey as well? Yes, Um, I don't know that we would have gone on the path that we did in the way of raising capital that we did if we didn't find those right partners. And um, it hasn't always been easy, like We've gotten plenty and many uh knows as we've gone through the process, and you definitely have those moments of you know, do you need to pivot the business model? Do you need to take capital from somebody who might not be as mission aligned?

And I think for us it was really important that we stayed true to that because we never would have been able to stay as true to our mission as we have been able to if we didn't have the investors that we do UM, and truly feel grateful every day. You know, we are a company that feels it's really important to make statements on you know, things that are happening in the world. Our investors actually reach out to

us and say, like, we're proud of you. There's not that debate in the boardroom, and I think that that is a really key part for us of being able to do what we do well. What advice would you have for any female entrepreneurs here at Collision, Yeah, well, I'm really inspired by the concept of time travel. As I said, it's going to take two hundred years for us to reach parity, and I don't want to wait

that law. So when I think about this as somebody that's driving impact, I always think about what I can do during my day to cut out the bullshit which is your favorite thing in your podcast, UM, and to really make sure day to day I am thinking about what's going to have the most critical impact on the business, on the mission, and on really changing the shape of the future. Yeah. I mean the other thing I would just say, and especially for people that are here, it's

great that you're here. It's really important to build a network. UM. Our earliest investors were people that we knew, UM, that knew us, believed in us, and we're like, yeah, this business feels like it'll it'll be great, But I believe in you, Caroline and Lindsay UM. And so I do think it's really important to constantly be investing in your network and in your relationships UM, because that's ultimately I think what what helped us out of the gate was

people that believed in us. So you also produce an excellent podcast at Chief. I listened to every episode. Thank you for plugging the New Rules of Business by Chief, a wonderful podcast you can download now. Russ and I am going to steal a trick from you because there's a question that you ask everything you know your guests in every episode, which is what is the best piece of business advice you've ever gotten? I will go first, Um, we got We've gotten so many great answers to this

on the podcast. I feel like a lot of pressure, um of of coming up with something like new and novel, But I actually think to me, and it's something that I have to tell myself daily, is don't let perfection

get in the way of progress. And particularly for a mission based business that um, you know, you want to hold yourself to a higher level of and do all of the right things, and the reality is you're not going to be perfect, you're not going to get it right, you're not going to have the right position on everything, and you might be a little late done something. And I think it's important for us to give ourselves some forgiveness on that and to give each other some forgiveness well.

And on the topic of networking, as we're at this amazing conference, I met somebody at dinner last night who said it was important to increase the surface area of serendivity, and so I think meeting people, forming relationships, getting to know different people from different walks of life, it's really important in business. Even if it doesn't make sense short term, it could really pay off long term. You literally said last night at the dinner, oh, I'm going to steal that,

and you already have. I did so. Thank you to the kind person who sat next to me at dinner. Fantastic, all right, Caroline Childers, Lindsay Kaplan, thank you give it up for chief please. After we exited the stage, we spoke in depth about what it means to be co founders with shared values, what women are up against, and why every company is inherently political. That conversation right after the break. Okay, all right off the stage and into the booth. The bo that was a ton of fun.

Thank you, thanks so much for inviting us. So now that we're in the booth, we can get at the realty. Um So I want to just do a little more about your background, let people get to know you a little bit better. One of the first questions I had was have you always known that you wanted to be entrepreneurs? Actually,

probably the opposite. And I actually really love telling this story because I think so often you hear the founder stories that are like I knew from early age and I was, I was doing my lemonade stand in my paper route, and I was an entrepreneur even early days. And I think for me, so my family had a family business, a travel agency, and so like the family business was hard, and I remember seeing that and thinking like, wow, this is like such a hard journey, and therefore almost

thinking I'm going the opposite way. I'm going to like a big company with yeah, yeah, And I started my career that way, and it wasn't until after business school that I pivoted over into startups and I was like, oh, this is where I meant to be. And it was only then that I started to think, I don't just want to work for somebody else, like I want to

build something myself. And it wasn't until the idea of chief came around that you could get to a place where I can dedicate my life to this type of business, this type of mission. Um. But it was very late for me in my career or later in my career that I really started to think about startups in general and being the entrepreneur my self. How about you, Lincy. You know, I don't think I grew up thinking about business.

I wanted to be an artist, so I wanted to be a painter, that I wanted to be a writer, um, And I think business became something that I just needed to do to pay the bills. And it became really clear really early to me when I started that I was a little anti authority, that I didn't like paint what to do and reflecting back, I also come from

a family of entrepreneurs. My grandfather owned a business, my father owns a business, my mom's a real estate broker that works on her own and so it makes a lot of sense that I found my way towards entrepreneurship as an anti authority kid of parents who wanted to do their own thing. Cool. Well, you know, entrepreneurs are rule breakers too in their own way. I certainly resonate with that. You and I share a more creative background,

and I I get that completely. So, Caroline, you have been an athlete for big parts of your life, and I wondered if you could talk about how you think that translates into being a CEO. If it does. Yeah, absolutely, um So, yes, I grew up playing sports. I almost every weekend was traveling, and I a basketball team my

road in college. Um So, you know, the idea of team and that collaboration was just such an important part of what I think I brought into you know, any type of business, any type of company, and it's something that I brought, you know, as I was starting Chief and the type of culture that I wanted to build.

But I think the interesting thing about so much of you know, me and my leadership and it being defined in sports, is it actually made it somewhat hard as Chief got bigger because you're used to like a team that is, you know, a team of twenty, and you're like, you're actually like in the in the trenches together, and then you get to a bigger company You're like, Okay, now this is a different type of leadership. This is a different way of leading an organization from the coach

to the commissioner. Yeah, I guess something like that. I don't really know if I like that analogy of who I am, but but there's something really meaningful in that transition that you have to go through that the sports analogy only took me so far, and like the entrepreneurial journey, and there was a definitely evolution that needed to happen post that, right. Yeah, And I was also looking at

some amazing statistics. You're not the only one, like something like ent of Fortune female CEOs played team sports and a big percentage of them, somewhere in the high fifties made it all the way to college, and the others all wanted to be artists and writers. Right. Thanks to the shoutout Caroline, so lindsay as co founders, I'm interested in how the two of you decide to divide up leadership duties in the company. Your title is Chief Brand Officers. Yeah. Yeah,

and it's it's a really clear division. I think at first, when it was just the two of us, it was a little sloppier because it was two people attacking a project. UM. And as chief got bigger, as the team grew, it became really obvious Caroline is the CEO, incredible operator, just a brilliant business leader. UM. And I love to be the storyteller. I love to kind of dig into the content, the creative and it became really clear that my domain

would and should be around my superpower. So I own brand, marketing, partnerships, editorial, all of our events, and Caroline owns well just about everything. Right. Well, I think it's actually an important evolution that a lot of startups have to go through, which is we were co founders and it was you know, a we are founders, co founder lead. But now we're a senior leadership team. UM, and there's you know that that broader, amazing suite of

people that have come on this journey with us. Now that the divide and conquer is not just about like how do we both divide and conquer? But how do we as an executive team and a leadership team really divide and conquer. And how how big is the chief team? Now we're over two hundred people staff. That's a lot

a lot of growth, and a lot of it virtually. Um. So we were probably around thirty when you know, the pandemic hit and we went into a bit of a hiring freeze as most people did, of just trying to figure out what the world was going to be. And we actually saw some really great growth over that period of time. We started to hire again, but all of it virtually. Um. Even if we were hiring them in New York, you were still hiring them virtually because nobody

was in person. And so it's been really important for us to just figure out how do we not only tackle the challenge of maintaining a culture as you get bigger, but maintaining a culture as you get bigger while in

a brand new way of working. Yeah, well it's interesting also, you know, as I was listening to you talk about the shape of chiefs business, and I can't think of a better pair to run a business life chief because part of it is business and operations, but a huge part of it is also just the experience and in a lot of ways, you are also a content company,

which is really interesting. I hadn't really thought about that. Well, you know, when Caroline and I were pitching early investors, and you know this conversation very well because it's stuck with us. We heard so many nose It was just no after no after no, like great idea, I love you too, and it's a no from us UM and want to invest Star said, I love what you do, but guys like I invest in great products, right, Like I, I invest in a company that makes one thing and

sells it and they do an incredible job. You're doing five things right. You're doing these peer groups, you're building an entire digital social network, you're putting together events, you have spaces like this is a company of five to seven depending on how you slice it services, and so it's it's a complicated business, but when you're offering a membership to these incredible women, we did want to make sure we gave her a really incredible, impactful experience that

covered everything that she was piecemealing together. So we wanted to take the place of the coach of the conference, um of the content and really make sure that she had an a list holistic way to become supported and become a better leader. Staying with this theme of the two of you for just a minute, I've gleaned from listening to your podcast and also just hanging out with you for the past you know, seventy two hours, which has been super fun, that the two of you have

very different personalities. We do this. I want to grow it back to you, be like, how would you describe those two different personalities. I'm not even gonna touch that. Um, Dr Jekyl and Lady Hyde. You're very different, but it obviously works incredibly well. So is Do you have any relationship advice for other co founders, you know, because partnerships are hard. I have a co founder. Occasionally we fight

like a cat and a dog. Like starting a business is stressful and difficult, and the two of you have you're very different, but your chemistry is is amazing. Yeah. Well, I mean, I think the thing that we realize very quickly and why we therefore wanted to do this together other is that we are very different. Our skills are very different, our personalities are very different, but our values

are not different. Um. And we talked a lot about what we wanted chief to be from a you know vision of the business, but also a vision of the culture, and we just it was really important for us that we were very aligned on that um upfront, because that that's really hard to have a disagreement about. It's pretty easy to have a disagreement about, like I think we should do this different design or that different design, and like those are just so they're they're surface surface, surface

level decision making. Sometimes we may disagree on but the values that Caroline and I share are so similar, and so when people don't know us well, we've gotten the like on the on the scale between Lindsay and Carol and I'm right between you two, and we laugh about that because we're we feel like we're actually very close

together on that scale. We're not really sure what that scale is because we often, and this is so reassuring, we often come to the same conclusion and we get there in such a different way, and when you hear

somebody else it's almost like we're doing the math problem differently. Yeah, Caroline actually doesn't show my work show write a deck, and I'm like, my gut says this um, And we get there almost always to the same place, and it is that much more um compelling to say, I feel so good about this answer because I not only trust you, but I trust that you went there a different way

than I did. Yeah, And maybe I'm just thinking, like maybe that's an advantage of being a purpose led business in a way, right is, If you're just making a widget or a product and you don't have some larger purpose that you're pursuing, like, it would be easier for founders to get off track and disagree and fall apart, whereas the fact that you've signed up to like change the world right like that keeps you aligned in a way.

I think it's actually harder for our team than it is for us because I care about certain things deeply impassionately, and she cares about things deeply and passionately that I might not as much because we both think about things differently, and they have to actually like bridge that gap of like two people who like deeply care and will come at something from a very different place, but they have to kind of satisfy both. That would be a that was a hard thing early days for some of our

team to to overcome. Now I think that's um less of a I need to manage to co founders and again, it's that broader senior leadership team. But I actually think it's something that for us was really important that we recognize could create a struggle for the team of of navigating two very different ways of needing to present an idea, like I need it. I need to get to a place from a very different perspectives. She needs a deck. She needs a deck. Everybody she needs a deck. She

needs the charts. I need an analogy, right, I need to get excited. But to be fair, like I love data and you love a story. So again, I think sometimes, um, people fall into thinking we are more stereotypically different and caricatures of ourselves than we are. That's great, Okay, I don't really even know how to ask this question, so

we'll see. That's it. Nailed it. So we started to talk a little bit about this on stage, but I wanted to dig more into my metaphor is the obstacle course that women need to run through in order to make it into leadership positions in business. I just love to hear your observations about those obstacles and how Chief is trying to help women take those on. Um. Yeah, I mean I think that there's so many different aspects

of the challenge. There's the external factors of as you're getting more senior, you're likely starting a family, you're likely starting to take on the responsibilities of child's care, and we know that that burden so much more goes to women inside the office. There's um both the unconscious bias

that you're battling, but it's also your your own. I think there's so many studies that talk about how women need to have a hundred percent of the qualifications of a job before they apply for it, where men are like, good, fifty to sixty king that one a shot, he's got potential. I had a job once I know how to do this. Yeah, So it's not just you know, the factors that other people are putting upon them, but it's also how they

are conditioned and other things things. And I think one of the most important parts of CHIEF is that you have two things that come out of an amazing network of other women. One is it normalizes things for you of just like I don't have to have all the answers, um, I don't have to have the perfect work life balance that so many people talk about and nobody has. And it also really helps to motivate people to take risks. I think that's one of the most powerful and fun

parts of cores. You walk in and you talk about, like what is it that you really want to do and be, and you hold each other accountable to that, and so now you do maybe apply for that thing or go for that stretch assignment that maybe you're at fifty percent of instead of a percent of. And so I think it's all of those small things that having

a network like CHIEF can really bring about. Yeah, yeah, I mean the expression it gets lonely at the top up, it gets lonelier a lot faster when you're a woman, and a woman, to Caroline's point, is battling not just everything happening in her life at that time, but just the unconscious bias that comes with being a woman. I mean, We're at a conference and I'm worried about what I'm wearing on stage. I don't give a ship about my clothes. I don't care about shoes, and yet here I am

feeling like I need my hair and makeup done. I'm going to get judged on my shoes, which by who, I don't know. I think women are constantly battling with stereotypes about their age, the motherhood penalty. So there's so much that they are up against, and when they finally get there, we ask them to speak on a panel, we ask them to mentor we hold them up to such a high standard on top of them just doing their job that they are now teetering at this very

tall precipice. And we wonder why women get burned out. We wonder why they're leaving the workforce. I think we all know, and yet we're not doing enough to support women and to really give them strength when they get there. Yeah, agreed. Um. Yeah. So another area that's related to this that I wanted to sort of dig into a bit is an area that you cover in several different dimensions in your podcast. Um, and it's in the past, and I think still right. There are a different set of rules for women in

business than for men. There are different ways that women are judged. To the point that you just made lindsay in the workplace, can you talk about some of those rules, how they're different for men and women. In the podcast, for instance, you talk about some of the issues around bringing your whole self to work, some of the issues around like humor in the workplace and the different different sets as a as a self proclaimed funny person. You know,

men are Men are rewarded for their jokes. Women are taken less seriously. Um Women in the workplace are often expected to pick up the birthday cards, bringing the cupcakes, take care of a lot of the the thankless work that is so important in the office around culture building. What does that mean, We'll let the ladies handle it, right, So we know that women are constantly being judged around being apathetic, showing up being nice, right, Like, we just

interviewed somebody who was like, fuck, the word nice. Nice gives us nothing. Nice can actually be toxic. And yet as women, we feel the obligation to be liked because if a woman isn't liked, she's known as exactly right, so it is I've seen that happen a million times. But if you're too nice, yeah, then you push over your doormat exactly So we put women on this tight rope of be funny but not too funny, be empathetic,

not too empathetic. And then we also don't talk enough about the intersection of women who are you know, from underrepresented minorities in the workplace and everything they have to juggle on top of that to be this model worker.

So again, like it's it's such a narrow tight rope that we've put women on um and it's why we built Chief to make sure that there is a supportive community where we can normalize these problems and make sure that we talk about it and we try to fix the systemic issues that are facing women and executive women in the workplace. Step one, be aware that there's a problem. Step two applied to Chief. My co founder Rosary says all the time, like, it's not important to be liked

for for women, it's important to be respected. But I don't know if I fully agree with that. It's really hard as a woman to be respected without being somewhat liked, right, Like it's it sounds good in theory, but if you're not liked, you're kind of implying your disliked. And to be disliked as a woman is really difficult. And I can name some women who are disliked and have been taken down because of it. So your reputation becomes everything, and so it's easier to say, it's harder to do.

So let's pivot and just talk about purpose and purpose sied businesses. So a lot of the purpose led leaders that I've talked to measure impact, you know, beyond kind of the traditional R o I financial measures. What do you measure at chief? Like how do you decide whether you're succeeding or not? I mean, I I assume you measure financial metrics as well, but are there things beyond that? Yeah?

I mean our mission is to drive more women into positions of leadership and keep them there, which I think creates a very clear definition of what does success look like. And that is what is the representation of women people of color in leadership? And unfortunately, we are right on the heels of a pandemic where it is disproportionately affected

women dropping out of the workplace. And so for us that means that our role and our job just got bigger, because even before the pandemic, it was going to take two hundred years before women reached the same level of representation in senior leadership UM. And so for us, that

is like the macro like what do we measure? How do we how do we continue to strive to do something that will create a ripple effect that will help to change some of that there's a lot of things that we measure internally with like the members that we do have of you know, what new opportunities have they got in UM, and also things that are just a little bit softer in measurement of just you know, how confident are they feeling in the leadership positions that they're

in and how supportive has your network expanded? Are you making more money? Right? Yeah? Is there more opportunity? Right? Like there's there's the softer questions that I think are really leading into into austin knowing we're driving impact and I think that the more difficult question for us is the macro change we're seeing when we're up against the pandemic, when we're up against a recession. So you know, two

steps forward, one step back. Yes. So a lot of the companies that we have featured on on this podcast are also certified B corps. You're not a certified B are you? We're not? Have you ever thought about UM? I did very early days of of founding Chief, And I mean, I think the things that are really exciting about being a certified B Corps is that UM in order to become that, you have to be measuring some of those other things, and you know you're you're broader

um impact. And I remember looking at it and being like that, And I will say candidly like that almost feels like table stakes for us, Like that is what we are. So it might be something that we decided to do down the line, but um, I think for us, we wanted to just make sure that we were most focused on the mission and the impact that we were trying to drive as our central mission. Right, Yeah, we've we've thought about it also, and we are not a certified b although I think we are going to head

down that road. So let's see, we'll let you know what it's like. So we've talked about this before. Also, I really believe that being a purpose led business is a journey and no no company is perfect, nor should we expect them to be. But taking on a social justice issue as you have with Chief in some ways can make you a target. Do you ever feel additional pressure because your purpose lad and because you have such

an inspiring but weighty mission, I would say yes. I think the hard part is when you have something like really focus on women in business, there are many different social issues that all factor into that, and so I think it's actually really most important and like most pressure filled of where do you draw the line of what you feel like you should be weighing into versus not um And I think that's honestly where I feel the most pressure of wanting to you know, in our our

members are eager for us to to play some of those roles, but we're also running a business and we have to make sure that we are focused on the mission that that we have built chief for and can't weigh into everything and do all of that at once. And so I think that to me is one of the biggest pressures. Less so about like what do you specifically say about this one thing, but it's more of how do you how do you make that determination of what you want to stand for? I think also the

pressure to weigh in on everything. It's not only difficult to running a business, but it's difficult to focus. And so we saw an outpouring of support around the rumor that Roe v. Wade will be overturned. Right, it was

in the news. Every organization is making a statement, Um, we signed the don't ban Equality coalition, and yet two weeks later there's a shooting, Right, and you don't hear anything about Roe v. Wade, right, and so like, it's really difficult to stay on top of what you believe in and the causes that you absolutely want to support when the news cycle is changing, public opinion is onto

something else. And so it's really morton for us to make sure we're clear about what we stand for, that we commit to what we stand for, because if not, it starts to become performative, right, Like, it's not actually healthy for a company to be taking a stand writing

a statement every three days about the new topic. We really want to make sure we're doubling down on what it is we stand for, what we ourselves can commit to, and going all the way, so that we're not just writing a statement, posting it on LinkedIn and moving on, right, And we want to make sure our members and our broader Chief community understand what we stand for and know that when we take that stand, we are doing it and we are doing it all the way and it is part of who we are and it is baked

into the DNA of Chief. Yeah. Yeah, just to build on that on this podcast, Obviously, one of our big themes is this issue of we call it purpose watching. In other words, saying that your purpose letter consciously capitalist enterprise but not really meaning it. And lindsay, I've heard you say that you think that a lot of brands just need to knock off in quotes, knock off their performative bullshit, which I loved. So it sounds like you agree right that it's it's a problem in the world.

I think a lot of companies are torn. I think that they want to say something, they don't want to go all the way, and they end up kind of like mincing their words and staying in the middle. If you want to say something, say it and do it right. Like at this point, I think consumers are really smart and for the most part, especially younger consumers, really want to align themselves with brands and companies that follow the same set of values. And so if you're going to

do it, do it right and do better. Because there's so many companies out there now that I think I want to put out the statement, want to get the like box checked. Particularly d e I Right, we're gonna hire a d e I person. We're gonna we're gonna make a claim that we're going to do something. And again, you don't have to boil the ocean. You don't have to, you know, make a statement about everything, but at least, if you're going to do it, pick a topic, pick

an issue, commit to it and do better. Yeah, yeah, I love that, And um, the statistics are incredible. It's like n of young people expect companies to take a position now and they expect c e O s to be out talking about the position that the company has. Yeah, and you know a lot of companies say we're not political.

Well guess what. If you're giving your employees healthcare, if you're making decisions about their time off when they become new parents, you're making political decisions, whether you want to or not. Right, that's a fantastic point. We've forced companies to be political, and so you have to be educated on some of these broader issues and some of these social issues. You have to be to lead a company because you're making those decisions. You're deciding, you know, where

your company is incorporated and how you're paying taxes. So you're political no matter what. Totally. So you know, this idea of of being purpose led has been talked a lot in the investing community as well. Sometimes it's called E S G investing. Sometimes it's called impact investing. Does that ever come up with your investors? I know we talked about on stage that you you do try to find values aligned investors, But have you ever gotten any

pushback from potential investors because of your purpose? In other words,

is there any friction there for you? I mean, if they had it, they didn't explicitly say it because they knew that the mouth day, because very much could be behind you know, some people's questions of is this an investment that I want to make um while not explicitly said to us, I think the bigger thing for for us and someone of how I think about it is I love that there's this attention on you know, E s G investing and impact investing or investing in women

led businesses and investing in businesses that are being built by people of color. Like, I love that it's getting attention. I just don't want it to be siloed that it's only one type of investor that should be investing in that type of thing, or only women investors that are investing in other women. I actually just I hope that like the broader investment community starts to look at and say, like, these are just good investments. Yeah, it's just called investing. Yeah. Yeah, yeah,

Well it's a process, right. I believe we will get there, I really I do. It'll take take maybe some time. So do you think do either of you think that being leaders of purpose led businesses is I guess more difficult than being a leader of a traditional company. I mean,

I think leadership, no matter what position you're in, is hard. Um. I think it gets harder every day as expectations of leaders making statements, making stands, needing to take the role that traditionally had been held by government because people are losing faith in that institution. I think that there's a really hard challenge across the board for all leaders. I think the aspect of it that sometimes can feel more challenging and being a purpose led business is that sometimes

the acceptance of error is less tolerated. That when you are making statements and trying to do good, when you inevitably make a misstep. She's looking at me when you lin you Lindsay kaplan inevitably missed up. And we had this conversation to get really personal. I called Caroline a few weeks ago really upset because I just felt this pressure on our calm side on on our events team to make sure that we are delivering a rapid response

when shit happens in the world. And I felt like I missed something and I wasn't sure and I I called you so upset and felt like I was going to be disappointing members and if not today, then when will that happen? And Caroline said to me, it will happen. It's not an If it happens, you will fuck up, and it's okay, and I will support you because you will funk up. We will funk up, you said, we not you. She met you. She said, we will. We will fun up, and we will get through that. And

let's just make sure that we acknowledge we're human. We're not perfect. We're trying our best, and we hope that our ore again, our broader community understands our values and our mission and knows that we're human and will be there to forgive us when inevitably we sunk up. And thank you for Thank you for being so wonderful to me, Carolyn, because no, it was. It's it feels like a lot of pressure. On one hand, I think leading a purpose built company, it's a rallying cry. I think our members

believe in our mission. It's why they joined our team members, right, Like, on one hand, there is so much love for that mission and passion and it brings good people. It's a magnet for great people. But on the other hand, it can be really polarizing. UM, And there's a lot of cushion. The bar is high, and I will fall off that bar. First, I'm gonna go to the bar. Then I'm gonna fall

off the bar. Yeah. So beyond the the two of you, because you obviously totally have each other's backs, are there other female leaders or founders that you particularly admire and drawing inspiration from. Yeah, I mean, I think so many members that we have that are a part of Chief. It is the amazing aspect of building this business is that we also get to tap into just amazing community of aspiring women leaders. And we joke all the time.

We're like when we do a podcast or we're you know, on the stage and collision and we're like, it's it's kind of funny that it's the two of us, and we've got some members that Chief that are like a lot more impressive than both of us. UM. And So I think it's just this like inherently built into the DNA of what we get to do to be able to tap into a community of fifteen thousand women that

are really really inspiring, um, which is amazing. You know, We've brought in so many people that have been speakers that have just been like so inspired r Michelle Obama, Percella Burns, like mal Cleany. It just has been like an amazing you get incredible speaker. It's so yeah, and and I literally am like, this is the business we're running. But at the same time, like it's a master class every single day for us of you know what good leadership looks like to be able to be in that ecosystem.

Yeah yeah, well well put okay. UM. So to wrap this up in the spirit of it's a journey and nobody is perfect, we have a tool on this podcast called the VS Scale. The idea is to rate companies on the gap between word indeed, I e. How closely are you following your stated purpose? And our scale goes from zero to a hungard zero being the best, zero bs, a hundred being the worst. Glad to clarified, I would have got total b s. Yeah. Yeah, it's easy to

flip that around. So hundreds of the worst total b s, so the worst purpose washers out there get high scores on our scale. I want to ask you both to rate Chief on that scale as it exists today and give yourselves a score. I feel like we should newlywed game this and like yeah, yeah, um well, in the spirit of women in confidence, I'm giving us a zero because we have been so intentional about our goal from day one. So I am a no bullshit person. One

of our brand values is no bullshit. Well we changed it to we had to our Chief people officer was like, we shouldn't have a curse in our an explicit word in our values. Oh is that right? So wait, what is it now? Real? It used to be noble ship and we change the value in the word. Yeah, I got you. Well, you know you're like like yeah, I like no bullshit. You know, maybe maybe you two, maybe there's a little bit of like, um, you know, maybe we're not perfect, but I think we're pretty. We're pretty

no bullshit, very little bullshit. Like there's there's like, you know, we're a company, so it's almost like are there no nuts? I don't know. Maybe this gets made in a nut factory where there's traces of nuts, maybe there's traces of bullshit. Um, but I think our intention is no bullshit. Yeah, i'd create us a little bit harder, but I actually it depends on like exactly what we're measuring this. You can tell I'm a data person, like I immediately going to

like being specific about what we are measuring on this scale. Honestly, I think the reason why I give us, you know, probably like a i'd say thirty, let me give us a thirty is honestly because it is honestly because we're three years old and like, okay, we're like we always want to be at a place of doing more than we're saying. And I think that is a fundamental part

of like being a no bullshit company. And I honestly think that in the last few years, with everything that has happened, sometimes you have to because it's all that you're able to do in that moment, say a little bit more than you're able to do at that moment. And I think that given that we're three years old, that so much is happening in this world, that things are changing every day, that I am at a place of like there's so much more I want us to do.

There's so much more I know we can do, and that's not really a bullshit scale, which is why I'm like, what exactly are we measuring? But I want I just know that we can do so much more that I can't give us. I can't, at my heart give us a perfect score. I love both of those scores. Honestly, it's for us to do better. So I think we can do more. But are we currently bullshitting? No? I don't think we'll trace there's trace amounts of bullshit everywhere. You know, we could snap a bread of filter on

what we do and get down to zero. I think there's trace amounts of bullshit. Okay, Caroline Lindsay, I absolutely love the work that you were doing in Chief. I find the two of you to be so inspiring. I want to thank you for being on the show and thank you for hanging out with us at Collision. Such a good time it has been. Thanks for having us. All Right, folks, it's time for Chief's official BS score.

Caroline and Lindsay gave wildly different numbers based on their different interpretations of what the BS score is all about, and honestly, they're both right. Lindsay score of zero shows the purity of their intentions. Chief has been designed from the mound up with their purpose in mind. Nothing they do takes them away from it. Their purpose and their business are inextricably linked. But Caroline is also so on point when she says the Chief is a work in progress.

Every purpose led business is on a journey. The best leaders acknowledge their shortcomings and stay laser focused on making improvements to better meet their goals. Although let's be real, thirty is a little harsh, I'm going to give Chief a ten. It's one of the lowest scores we've given on the show to date because I truly believe that

Lindsay and Caroline's intentions are pure. But as a three year old company, it also gives them a little room for aspiration, room to grow into the impact that they're trying to make in the world over time. If you're starting a purpose led business or you're thinking about beginning the jour any of transformation to become one, here are three things that you can take away from this episode. One,

start with a problem that you care about personally. Lindsay and Caroline met at a super lame networking event and realize that there was something missing and networking, especially for senior female executives. They looked around the world and realized that that lameness was just one part of a whole system that holds female executives back, and chief was born. Choose your problem carefully and remember sometimes the problem chooses you. Two.

Surround yourself with people who share your purpose but not your skill set. Caroline and Lindsay couldn't be more different, and that's perfect. A successful purpose led business gets that way because everyone agrees on the problem blum and brings their own unique tools to solve it. And three, just because your purpose, lad, does not mean you have to have an opinion on every social or environmental issue that hits the news. There's an increasing pressure on leaders to

have a point of view. That's a new and very real part of leading a business today. But having a point of view on things that have nothing to do with your purpose can come off as as Lindsay says, performative bullshit. If we change the face of business for you today, subscribe to the Calling Bullshit podcast on the I Heart Radio app, Apple Podcasts, or wherever you listen

to people speaking to your Ears. Thanks to our production team Hannah Beal, Amanda Ginsburg, Andy Kim, D s Moss, Haley Pascalites, Parker Silser, Basil Soaper end Me, John Zulu, and a special thanks to the folks at Collision and to the entire crew at Chief Calling Bullshit was created by co Collective and it's hosted by me Ti Montague. Thanks for listening. M