November 9, 2022 • 66 mins
Chief cofounders Lindsay Kaplan and Carolyn Childers met at a lame networking event for women and realized on the spot that there was a dire need for something better, especially for senior female executives.
Today we talk to this dynamic duo about how that fateful event set them on a path to create Chief – the private network valued at over $1B+ focused on supporting women at the top and keeping them there.
Show Notes
- Listen to Ty’s full conversation with Lindsay and Carolyn at the Collision Conference in June 2022.
- Chief recently announced that they are launching in the UK. Read about it in Bloomberg.
- Watch Chief’s hilarious parody commercial “This Guy Means Business” and listen to their podcast The New Rules of Business.
See omnystudio.com/listener for privacy information.
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Transcript
Episode Transcript
Available transcripts are automatically generated. Complete accuracy is not guaranteed.
Speaker 1 (00:04):
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 asked
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
(00:25):
are now teetering at this very um 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. Welcome to
(00:47):
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
(01:09):
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
(01:33):
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
(01:53):
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
(02:15):
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
(02:37):
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,
(02:59):
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.
(03:21):
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
(03:43):
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
(04:06):
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
(04:29):
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
(04:50):
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
(05:15):
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
(05:35):
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
(05:56):
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
(06:20):
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
(06:41):
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
(07:03):
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
(07:26):
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
(07:47):
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,
(08:10):
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
(08:32):
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,
(08:56):
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,
(09:17):
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
(09:40):
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
(10:00):
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
(10:24):
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,
(10:46):
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
(11:08):
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,
(11:32):
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
(11:54):
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
(12:17):
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,
(12:40):
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
(13:01):
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.
(13:24):
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
(13:46):
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.
(14:07):
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
(14:27):
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
(14:49):
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,
(15:11):
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
(15:34):
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
(15:56):
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
(16:16):
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
(16:37):
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,
(16:57):
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
(17:17):
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
(17:39):
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
(18:02):
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
(18:22):
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
(18:42):
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
(19:05):
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
(19:25):
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,
(19:51):
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
(20:13):
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
(20:36):
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
(21:00):
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
(21:23):
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
(21:45):
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
(22:05):
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
(22:26):
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
(22:54):
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
(23:21):
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
(23:43):
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.
(24:05):
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
(24:28):
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,
(24:49):
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,
(25:11):
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
(25:33):
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,
(25:55):
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
(26:19):
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
(26:41):
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
(27:04):
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
(27:26):
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
(27:51):
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,
(28:16):
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
(28:38):
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,
(29:00):
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
(29:21):
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
(29:43):
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
(30:04):
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
(30:25):
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,
(30:47):
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
(31:10):
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
(31:31):
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
(31:53):
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
(32:16):
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
(32:39):
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
(33:00):
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
(33:24):
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
(33:46):
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
(34:07):
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
(34:30):
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
(34:51):
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,
(35:14):
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
(35:34):
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,
(35:56):
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,
(36:19):
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
(36:41):
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
(37:03):
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
(37:25):
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,
(37:46):
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
(38:08):
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
(38:30):
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
(38:53):
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,
(39:14):
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
(39:36):
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.
(39:58):
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
(40:20):
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
(40:43):
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,
(41:03):
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.
(41:24):
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
(41:47):
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,
(42:08):
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
(42:30):
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
(42:51):
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
(43:13):
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
(43:33):
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
(43:56):
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
(44:19):
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
(44:43):
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
(45:03):
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
(45:23):
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
(45:45):
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
(46:06):
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
(46:26):
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
(46:50):
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
(47:13):
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
(47:33):
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
(47:55):
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
(48:17):
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
(48:40):
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
(49:00):
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
(49:20):
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
(49:41):
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
(50:02):
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
(50:23):
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
(50:44):
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
(51:04):
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
(51:28):
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
(51:48):
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
(52:09):
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
(52:33):
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
(52:55):
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
(53:15):
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
(53:37):
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.
(53:58):
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
(54:21):
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
(54:41):
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
(55:04):
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
(55:26):
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
(55:48):
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
(56:10):
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,
(56:34):
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
(56:54):
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.
(57:15):
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
(57:35):
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
(57:58):
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
(58:20):
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
(58:42):
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
(59:03):
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
(59:25):
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
(59:47):
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
(01:00:10):
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,
(01:00:32):
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
(01:00:53):
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
(01:01:14):
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.
(01:01:35):
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
(01:01:59):
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
(01:02:20):
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.
(01:02:42):
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
(01:03:03):
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
(01:03:25):
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
(01:03:45):
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,
(01:04:09):
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.
(01:04:35):
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
(01:04:57):
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
(01:05:20):
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
(01:05:42):
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
(01:06:04):
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
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 asked
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
(00:25):
are now teetering at this very um 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. Welcome to
(00:47):
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
(01:09):
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
(01:33):
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
(01:53):
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
(02:15):
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
(02:37):
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,
(02:59):
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.
(03:21):
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
(03:43):
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
(04:06):
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
(04:29):
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
(04:50):
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
(05:15):
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
(05:35):
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
(05:56):
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
(06:20):
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
(06:41):
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
(07:03):
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
(07:26):
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
(07:47):
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,
(08:10):
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
(08:32):
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,
(08:56):
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,
(09:17):
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
(09:40):
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
(10:00):
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
(10:24):
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,
(10:46):
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
(11:08):
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,
(11:32):
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
(11:54):
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
(12:17):
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,
(12:40):
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
(13:01):
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.
(13:24):
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
(13:46):
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.
(14:07):
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
(14:27):
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
(14:49):
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,
(15:11):
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
(15:34):
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
(15:56):
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
(16:16):
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
(16:37):
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,
(16:57):
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
(17:17):
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
(17:39):
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
(18:02):
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
(18:22):
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
(18:42):
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
(19:05):
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
(19:25):
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,
(19:51):
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
(20:13):
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
(20:36):
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
(21:00):
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
(21:23):
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
(21:45):
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
(22:05):
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
(22:26):
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
(22:54):
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
(23:21):
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
(23:43):
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.
(24:05):
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
(24:28):
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,
(24:49):
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,
(25:11):
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
(25:33):
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,
(25:55):
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
(26:19):
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
(26:41):
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
(27:04):
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
(27:26):
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
(27:51):
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,
(28:16):
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
(28:38):
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,
(29:00):
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
(29:21):
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
(29:43):
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
(30:04):
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
(30:25):
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,
(30:47):
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
(31:10):
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
(31:31):
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
(31:53):
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
(32:16):
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
(32:39):
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
(33:00):
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
(33:24):
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
(33:46):
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
(34:07):
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
(34:30):
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
(34:51):
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,
(35:14):
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
(35:34):
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,
(35:56):
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,
(36:19):
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
(36:41):
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
(37:03):
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
(37:25):
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,
(37:46):
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
(38:08):
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
(38:30):
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
(38:53):
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,
(39:14):
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
(39:36):
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.
(39:58):
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
(40:20):
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
(40:43):
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,
(41:03):
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.
(41:24):
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
(41:47):
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,
(42:08):
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
(42:30):
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
(42:51):
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
(43:13):
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
(43:33):
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
(43:56):
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
(44:19):
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
(44:43):
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
(45:03):
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
(45:23):
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
(45:45):
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
(46:06):
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
(46:26):
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
(46:50):
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
(47:13):
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
(47:33):
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
(47:55):
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
(48:17):
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
(48:40):
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
(49:00):
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
(49:20):
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
(49:41):
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
(50:02):
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
(50:23):
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
(50:44):
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
(51:04):
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
(51:28):
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
(51:48):
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
(52:09):
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
(52:33):
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
(52:55):
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
(53:15):
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
(53:37):
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.
(53:58):
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
(54:21):
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
(54:41):
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
(55:04):
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
(55:26):
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
(55:48):
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
(56:10):
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,
(56:34):
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
(56:54):
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.
(57:15):
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
(57:35):
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
(57:58):
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
(58:20):
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
(58:42):
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
(59:03):
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
(59:25):
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
(59:47):
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
(01:00:10):
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,
(01:00:32):
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
(01:00:53):
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
(01:01:14):
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.
(01:01:35):
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
(01:01:59):
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
(01:02:20):
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.
(01:02:42):
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
(01:03:03):
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
(01:03:25):
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
(01:03:45):
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,
(01:04:09):
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.
(01:04:35):
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
(01:04:57):
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
(01:05:20):
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
(01:05:42):
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
(01:06:04):
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
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On Purpose with Jay Shetty
I’m Jay Shetty host of On Purpose the worlds #1 Mental Health podcast and I’m so grateful you found us. I started this podcast 5 years ago to invite you into conversations and workshops that are designed to help make you happier, healthier and more healed. I believe that when you (yes you) feel seen, heard and understood you’re able to deal with relationship struggles, work challenges and life’s ups and downs with more ease and grace. I interview experts, celebrities, thought leaders and athletes so that we can grow our mindset, build better habits and uncover a side of them we’ve never seen before. New episodes every Monday and Friday. Your support means the world to me and I don’t take it for granted — click the follow button and leave a review to help us spread the love with On Purpose. I can’t wait for you to listen to your first or 500th episode!