How Chief Built a $1.1 Billion Business by Boosting Women’s Careers

Startups are often born out of frustration. That’s especially true for Chief, a career development startup for women executives whose two co-founders crossed paths – as if by fate, or maybe irony – at a “really bad women’s networking event” in 2017.

“The wine is kind of warm and the conversations awkward,” Lindsay Kaplan, a co-founder and the startup’s Chief Brand Officer, told The Org. “We didn't sit next to each other, but at the coat check, we kind of rolled our eyes. But I think it is funny…and it goes to show that even at a bad women's networking event, there are still amazing connections that can be made.”

In 2018, the duo began building the New York City-based startup, billing it as a “private membership network focused on connecting and supporting women executive leaders,” and launched it publicly the following year. Kaplan’s co-founder Carolyn Childers now helms it as CEO — overseeing an operation of 15,000 members hailing from high-growth startups and top employers like Google and Goldman Sachs.

Even with its early wins, Chief has more to prove. The startup is valued at $1.1 billion, following a $100 million Series B round in March led by Alphabet’s independent growth fund CapitalG and joined by top VC firms like BoxGroup, Flybridge and General Catalyst. But with rivals circling the career development space, how did Chief stand out, build a powerful brand and grow to be the meaty startup it is today?

Chief’s roots

Though the co-founders didn’t cross paths until 2017, Kaplan thinks the general idea for Chief may have taken root much earlier. Kaplan grew up in a family of entrepreneurs: her grandfather ran a clothing factory in New York’s garment district, her father owns a bar and restaurant and her mother is a real estate broker.

The co-founders’ early career journeys also informed Chief. Childers and Kaplan both spent years working at buzzy startups before becoming entrepreneurs. Most notably, Childers was SVP of Operations at home maintenance startup Handy; Kaplan was mattress-in-a-box purveyor Casper’s first employee, and as its VP of Communications and Brand, she helped scale it into an operation with hundreds of workers.

“I grew into a real executive, I was being asked to mentor, I was sitting on panels, I was speaking and a lot of people were coming to me for advice,” Kaplan said of her time at Casper. “And yet I realized outside of my executive coach who was fantastic, I really didn't have anybody that I could talk to about these critical business decisions, and these really important leadership questions in my career.”

Building a brand

After the lightbulb moment at the unforgettable “bad” networking event, Kaplan and Childers got to work. By 2018, they had quit their day jobs and were all-in on building Chief.

It’s a compelling proposition: For every 100 men promoted to manager, only 86 women are promoted, according to a 2021 study by consulting firm McKinsey & Co. The pandemic may have exacerbated gender workplace disparities. Women reported being even more burned out in 2021 than in 2020 — and the burnout gap between women and men almost doubled, the study found.

Originally, Chief would center around in-person “clubhouses” in major cities, starting with New York. When it launched in 2019, Chief had 200 members and a “giant” waitlist — but then the pandemic hit. Uncertain of the future, Kaplan and Childers quickly pivoted to a hybrid model. “That allowed us to really grow exponentially, now that we weren't beholden to having these meetings in person,” Kaplan said.

The power of peers

Chief’s most popular offering: “Core groups” – or peer groups of 10 other Chief members and a dedicated executive coach that meet monthly, “specifically curated to make sure that you're with a group of people who ‘get it,’ who may not come from the same role, industry and function, but can bring that diverse perspective,” Kaplan explained.

Membership costs run from about $5,000 and $8,000 per year, a tab that more than 70% of members’ employers pick up in the name of professional development. The company also offers workshops, a digital platform to connect with other members and clubhouses in New York, Los Angeles, Chicago and San Francisco. Guest speakers – like Michelle Obama and renowned tech journalist Kara Swisher – give talks for Chief’s community as well.

Branding can also be tricky. Chief is careful to draw distinctions between itself and infamous coworking startups like WeWork and The Wing, a failed 12,000-member coworking enterprise for women (where locations were replete with “curvy pink interiors that recall the womb,” per The New York Times) that shut down in August after allegations of a toxic workplace and exclusionary practices.

The startup’s four clubhouses are “not coworking spaces…they definitely feel more like hotel lobbies,” said Kaplan. “They're more for members meeting each other, taking calls, taking meetings.”

To attract and support its own workforce, Chief has embraced a remote-first model. A little over half of Chief’s 230 employees are based in New York, where Chief offers (optional) office space; the rest are scattered across the U.S. The startup offers a wellness stipend, a “work from home” stipend and other perks.

“I have learned so much from the members of Chief about what leadership looks like,” Kaplan said. “I think that taking care of your people and treating them like humans is everything.”

Catching investors’ eyes

Chief has a compelling business plan, but is it worth $1.1 billion? Laela Sturdy, a longtime General Partner at CapitalG who led Chief’s Series B a few months ago, sure thinks so. She first heard about Chief a year before she invested, when a friend raved about her experience with it — and Sturdy saw her own experiences reflected in its mission.

“Having navigated my career, often the only woman in a boardroom, or just having that feeling of otherness and wanting to connect to other executive women, it was incredible to see the momentum they have built around building this community,” Sturdy told The Org. Including its latest Series B round, Chief has pocketed $140 million worth of venture capital since 2018, according to PitchBook data.

Sturdy is especially bullish on the pace of Chief’s growth — from 200 to 15,000 members in just three years — and says the peer groups are her favorite feature.

“A significant portion of the growth comes through referrals and organic growth, which speaks to how much people love the experience and the membership and being part of the Chief community,” Sturdy added. “They just have incredible product market fit…these are women who have significant executive responsibility and there are budgets to be able to invest in their personal development.”

Competing with the clock

Chief boasts an unusual core company value: “Time travel.” Looking forward, Kaplan said she’s always looking for ways to beat the clock.

“Our biggest competitor and the one that we constantly talk about is time,” she said. “I know that sounds silly, but the women who join Chief are some of the busiest people in the world. These are caregivers, these are professionals, these are people who don't always have time in their day to think about putting themselves first … How do we provide the most value in the most concentrated way to make sure that we are being really mindful of how little time she has left in the day?”

DeLoreans aside, Chief will also have to beat out rivals – including smaller industry groups, trade associations and private coaching services.

“We saw aspects of competition…but no one that was holistically offering what Chief is offering,” CapitalG’s Sturdy asserted.