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The Mission-Driven Ambition of Carolyn Childers

Creating Chief, the $1.1 Billion Community for Executive Women

Hey! Justin here, and welcome to Just Go Grind, a newsletter sharing the lessons, tactics, and stories of world-class founders!

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I’m a Venture Partner at VITALIZE Venture Capital where we invest in pre-seed and seed-stage WorkTech companies - People-first, data-driven, BIG ideas that transform work outcomes.

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Carolyn Childers, Co-Founder & CEO of Chief

Carolyn Childers - Chief

Carolyn Childers is on a mission to help women maximize their leadership impact.

As the co-founder and CEO of Chief, a vetted community for senior executive women, she raised $140 million and built a company worth $1.1 billion in less than three years.

Not bad considering Carolyn couldn’t even get lawyers to work with her initially because they thought her company shouldn’t be venture-backed.

In 2023 Chief was named one of TIME’s 100 Most Influential Companies and today they have more than 20,000 members.

How did Carolyn build a company this big and this impactful this fast?

Let’s get to it.

Early Days

While many founders we’ve covered on Just Go Grind had the classic lemonade stand or paper route growing up, inevitably leading to them becoming entrepreneurs, this wasn’t exactly Carolyn’s journey.

Though Carolyn grew up in a household of entrepreneurs, with her family owning a travel agency, she had her sights set on the corporate world.

After graduating from Boston College in 2001 with a finance degree, she got into investment banking, joining Deutsche Bank:

Going into investment banking right out of college just felt like a really good training ground.

I didn't think I wanted to be an investment banker for the rest of my life but being able to get into a discipline and an organization where you would just learn such good business basics was the plan.

I didn't know where I was going from there but the entrepreneurial idea was not even in my head.

Carolyn Childers

After a few years at Deutsche Bank, Carolyn worked for Avon before attending Harvard Business School in 2006.

Later reflecting on getting an MBA, Carolyn told of how it led to her eventually starting Chief:

I feel like I got a lot of the fundamentals of the learning of business already and I would have learned some of the fundamentals of growing and scaling businesses probably better in seat than necessarily in a classroom but what I got from it were amazing friends and connections and the reason I ended up going over to startups was because of those connections.

I was sad that it was limited to just two years, and in some ways wanted to create the ongoing version of that with Chief, but if I did it all again I'd want to get to startups faster for sure.

Carolyn Childers

After her MBA, and a brief stint working at Victoria’s Secret, Carolyn spent an impactful four years at Amazon, working as the head of Soap.com under the Quidsi brand started by serial entrepreneur Marc Lore.

Marc provided valuable lessons for Carolyn on the qualities of a great leader:

Mark is somebody that continues to be an inspiration for me and the way that he leads organizations, no matter what industry or what competitive environment he's in, I've never worked for somebody who gives so much autonomy to people.

I walked into that company with zero qualifications to be doing what I was being asked to do and yet he gave me just complete full reign.

I remember at some point we were working through our initial buys of inventory before we were about to launch and I was like, “If you want me to hit the breadth of assortment that you want me to hit in time for us to launch I'm gonna need to spend a lot of money and not necessarily the minimum buys that we have. I don't know that we're gonna turn through that in great speed.”

He just pulled out a piece of paper, did a very quick contract between the two of us, and it was millions and millions of dollars sight unseen. [He said] I trust you, go.

That was really empowering. I had never worked, at that point, as hard as I did in that moment because of the trust that I felt from him and the thing I took most was the leadership qualities that he demonstrated and how much that drove everyone in the organization to truly be their best selves.

Carolyn Childers

A few years later, Carolyn was ready to put her leadership skills to work as the head of her own company.

Starting Chief

Carolyn spent a few years as the SVP of Operations at Handy, an online household services marketplace, before becoming an Entrepreneur In Residence at Primary Venture Partners in 2017.

That role expanded the more informal advisor role she had in Primary’s network years earlier.

They were already familiar with each other as the idea for Chief started to form. Soon after, Primary led Chief’s pre-seed round and later seed round.

While Carolyn worked on the idea for Chief by herself for the first few months, she soon brought on a co-founder, Lindsay Kaplan, who proved to be a great counterbalance:

We are actually very different and very the same all at the same time.

I encourage anybody that is thinking about starting a business and thinking about getting a co-founder, you should never get a co-founder who is exactly like you. Always make sure that you have just this really nice balance of skills, and that was very much the case for Lindsay and I.

I am much more of the operator. I think about: how is this experience going to be run? How do we think about scaling this? What is our strategy long term?

Lindsay is the creative, and she is the one who is maniacal about any experience that we’re launching, how that will actually resonate from a brand standpoint.

But at the end of the day, the thing that is most clear is that our values are aligned and that’s the thing that’s similar about us that allows for those differences to play out in a way that is playful as you described it.

We have a good dynamic in that way because we trust each other and we can come at things from totally different ways.

Carolyn Childers

Diving deeper, Lindsay’s brand-building experience was just what Carolyn thought Chief needed:

I grew up playing team sports my whole life, I love teams, it was a dynamic that I personally wanted and I knew when I was starting chief that when you say a “women's professional network” unfortunately the image that comes to mind is not one of a big aspirational brand.

You often go to a very corporate, stodgy feeling, and so it was really important to me as we were building Chief to invest in a brand in a way that could break through.

Lindsay was at Casper, she was one of the first employees there, and a mattress company is also not exactly an aspirational brand, but she had done such good work in helping to create that brand and I was excited to partner with her to do a similar thing here at Chief.

Carolyn Childers

Together, they’d work on an idea born from their own experiences:

The idea of Chief, it came from a very personal place of getting more senior in our careers and spending all of our time managing teams and mentoring others.

There’s the old adage of, “It gets lonely at the top,” but for women, it gets lonely a lot earlier.

I think what was unique about what we wanted to build was we wanted to focus on senior executive women.

There’s 5.5 million women who are VP and above in the U.S., and they are so often the speaker and so often the mentor, but they don’t have a great community or resources for themselves to continue to grow as leaders.

We felt like the ripple effect that could have of getting just more of those women into true positions of influence and leadership, the ripple effect that could have in all of the companies that they are employees and leaders of would be really impactful.

Carolyn Childers

But it was a struggle early on:

I remember very early days of even just trying to get a lawyer to help us establish the company and I was talking about wanting to be VC funded and I literally could not get a lawyer to work with me because they were like this should not be a VC funded business, this is a very nice lifestyle business.

Carolyn Childers

Fundraising initially proved challenging as well, given their unique model:

I think that there's a real challenge that you have as you are fundraising and it should just be something that you recognize is going to be a challenge going into it of trying to educate people on a very new business model.

I think the ability for people to say we're going to be the Warby Parker of X category or we're going to be the Uber of Home Services or whatever it is there's just such a benefit that you have of creating that analogy for people for them to be able to put it in a construct and we didn't have that.

It was really difficult then to educate people on that and I think one of our biggest challenges was you say that you are for women and automatically people think “oh well then that's half the size of market” and then you say “we’re for senior executive women” and they think “oh well now you're slicing it even further,” that was the challenge that we were always faced with was is this a big enough market for Venture Capital dollars?

Carolyn Childers

Another hurdle?

Talking to lots of male VCs who didn’t personally experience the problem themselves that Carolyn was trying to solve for women.

Nonetheless, the market opportunity in front of Chief was huge and Carolyn knew it from the start:

There were a lot of people that as I started to talk about it would go into a place of this feels like a non-profit not a for-profit business, but for me, we live in a capitalist society, I looked at how much companies had made, statements about wanting to drive representation, how much they budget for investing in their top talent, and thought there is a real business model here where companies should be supporting their female executives as they are are making these statements and I don't see why this can't become a for-profit big scale business.

There's also 5.5 million women who are VP level and above in the U.S. alone and so as we were focused on senior executive women, that's a $30 billion market. It's massive.

I wanted to be ambitious about the impact that we could have on the world and I thought the best way of realizing that ambition was to go and get VC dollars that really allowed us to think bigger and move faster.

Carolyn Childers

After raising a pre-seed round from Primary Venture Partners, Chief announced a $3 million seed round in October 2018 led by Primary Venture Partners and Flybridge Capital Partners.

By January 2019 they were ready to launch.

Wanting to stay focused, they started only in New York City with a small cohort of women and a physical clubhouse in Tribeca.

Their physical space was great marketing for them early on and an investment in the brand.

How did they get their first members, before announcing their funding round?

Friends and cold emails:

It was not just our closest friends, we definitely sent some cold emails out to people that we had never met before.

I remember some early VC conversations where we were showing them our first members and they were like “oh so are these just all your friends and Lindsay's friends,” we were like “actually no that's not the case.”

It was amazing. A cold email to C-Suite executives at Fortune 500 companies and people were excited to join.

Carolyn Childers

And what were members getting when they joined?

The main benefit is a curated core group of about 8-12 people that meets monthly.

In the very early days, before Chief started using technology and data to determine what makes a strong core group, these were all curated manually.

Members are matched with those who are similar in regards to:

  • How many people you manage

  • How big of a budget you’re responsible for

  • Your life stage (First-time parent, empty nester, etc.)

Almost everything else could be different. This is on purpose.

While Carolyn and the Chief team originally thought there needed to be more sameness, the diversity in function and other factors adds to the benefit of the group.

They aren’t just talking about the latest tactics in core groups, but more about the people problems and leadership challenges.

Their Salon Series and app provided additional value to members:

Women were hooked immediately.

When Chief launched publicly in January 2019, it had 200 members.

Given the membership fees at the time, $5,400 for VP-level women and $7,800 for those in the C-suite, Chief was at a $1 million in revenue out the gate.

By March, their membership doubled to 400.

Chief had clearly struck a chord with executive women, but Carolyn and her team were just getting started.

Overcoming Uncertainty

In June 2019, Carolyn and Chief raised a $22 million Series A co-led by General Catalyst and Inspired Capital.

By this point, membership had grown to more than 700 women from 500 companies and their waitlist was already 5,000 strong.

The influx of capital would be used to expand to more cities, with clubhouses in LA and Chicago.

Leases were being signed by the end of 2019, but, as the pandemic hit a few months later, everything would change, though not like you might expect.

Carolyn elaborated:

We started very in-person. We always knew that we would have this extension to kind of democratize the access and allow for more virtual connection, but the pandemic pushed us there a lot faster than we ever expected, because everything we were doing was in-person in March of 2020 when the pandemic hit.

We had actually raised our series A at the second half of 2019, we had signed a bunch of leases for spaces in LA and Chicago. We were actively going through build-outs, and the pandemic hit. We were definitely top of the list of every single one of our VCs, like what’s going to happen with this business.

The amazing part of it has been that all engagement with our community went up threefold.

Women needed this community more than ever. They were trying to lead through social unrest and business challenges that nobody had ever foreseen.

They were also mothers that were trying to figure out how they were going to balance homeschooling with being that leader and there was no playbook.

So something like Chief became needed even more and it completely changed our model that we were able to expand the number of cities that we extended into over that time and provide this value for more women in a time when I think it was needed most.

Carolyn Childers

In May 2020, Carolyn raised another $15 million for Chief, by which point the company was already at more than a $10 million annual run rate less than a year and a half after launch.

Wild.

Of their more than 2,000 members by this point, 40% are C-suite executives while 60% are VPs, the average age of their members is 43, and less than 9% work in a single industry.

They also have an 8,000-person waitlist.

Soon, Chief would become a unicorn.

Unicorn Status

After a brief moment of existential uncertainty with the pandemic, Chief just kept growing.

And growing.

And growing.

In March 2022 Chief announced a $100 million Series B, led by Alphabet’s CapitalG, which valued the company at $1.1 billion.

By May 2022 Carolyn and the team had grown Chief to 15,000 members and a waitlist of 60,000. They also have clubhouses in three cities in the U.S. by this point.

Let’s not forget, this is a company that launched less than three and a half years prior and they’re already at upwards of $100 million in revenue.

Again… WILD.

And, even though they raised $140 million in venture capital, the business had largely grown by word of mouth:

Word of mouth has been by far our dominant channel which is great because that means that we can continue to use the capital that we’re raising to invest in the experiences and not invest in a bunch of marketing channels.

Carolyn Childers

That investment in experience included their technology platform, a LinkedIn-like product:

Product and tech is where the biggest investments for us really are. Our platform in some ways is LinkedIn, MasterClass, and a dating app all in one.

There's a lot of investment that you want to make when you're kind of in all three of those categories and I think the unifying thing across all of it that we're trying to focus on is that personalization, that if somebody is coming in because they are trying to navigate a career change, that there's a very clear path of how they go and tap into this network to help them with that.

If there's somebody that's coming in because they were just promoted to EVP for the first time and they're just trying to step forward in their own leadership journey in this new role, that there's a very clear path for them.

If you have an entrepreneur that's looking to tap into this network as they are building a business for the first time… all of those are very clear use cases of all of our members that join, of what they need and want from this community.

Carolyn Childers

All of this in an effort to maximize the value members can get out of Chief.

Which makes a lot of sense considering the price by this point is $5,800/year for VP level members and $7,900/year for C-Suite members plus $1,000/year for clubhouse access.

And that technology platform by this time included an app with four main features:

  1. A core-specific product for members to communicate with their core group and talk with their guide

  2. A LinkedIn-like product to post for very specific needs

  3. A whole content library with all of the programming Chief has ever done

  4. A place to make intros, where Chief suggests connections within their ecosystem

The app, as Carolyn described in one interview, has a ton of engagement and high weekly active usage, a metric she much prefers over average session time given the users are busy businesswomen.

By January 2023, Chief’s membership had grown to 20,000 women from more than 10,000 companies including nearly 80% of the Fortune 100, and despite going through some growing pains and restructuring early in 2023, is primed for more growth.

Chief Today

As of this writing, Chief has expanded to clubhouses in five cities:

  • New York City

  • San Francisco

  • Los Angeles

  • Chicago

  • Washington, D.C.

Their programming has included incredible speakers like Michelle Obama, Indra Nooyi, and Amal Clooney.

The craziest part?

Over 70% of the women in Chief have their membership paid for by their companies.

It’s a phenomenal business, Carolyn and her team have executed beautifully, and it seems like they’re primed for much bigger things.

Where will they go next?

Carolyn’s Wisdom

In each edition of the Just Go Grind newsletter, I like to include a few more quotes at the end from my research into the founder who is featured, sharing their wisdom.

On raising venture capital as a mission-driven company:

I do not think that I would have any regret with the way in which we are going because I think we're impatient of trying to build a really meaningful powerful network for badass women that need this.

At the heart of the mission is to drive more women into positions of leadership and keep them there.

It's over 200 years before we get to gender parity in senior executive positions and if a little bit of dilution means that we can go and execute on that mission faster, I'm game.

Carolyn Childers

Advice for other founders:

There's a lot of people that have a tendency to get very five-year planned focused and “I need to hit this milestone by this date” and the thing that made me successful was that I just jumped to the thing that most gave me passion next and ultimately found the right place for myself.

The advice I would give for people is to not get so focused on needing that next promotion, that next thing, but to really focus on the learning and following what makes you excited.

Carolyn Childers

I actually think that the failures and the hard parts, the things that you didn't know, are actually where you learn the most about your business.

If you have too much capital that you are in some ways able to ignore the things that aren't going well and muscle through it by just putting more money into the picture, you don't learn what's working or not working for your organization… [Advice] I would give to anybody that's at a specific stage, whether it's unicorn status, their Series A, anytime that you get that influx of capital, it's to make sure that you really stay true to what's important and stay focused.

Carolyn Childers

Recent Founder Deep Dives

Thanks for reading!

Best,

Justin

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