Who are Carolyn Childers and Lindsay Kaplan — Chief founders profile 2027
Direct Answer
Carolyn Childers (CEO) and Lindsay Kaplan (Co-Founder and Chief Brand Officer) founded Chief in January 2019 after a chance dinner introduction in New York, with Childers bringing operator chops from Quidsi, Handy, and Avon and Kaplan bringing the brand and PR machine she built as Casper's first full-time employee.
Their genius was not the idea of a women's network, which had been tried and failed for decades, but the execution stack underneath it: a brand-led go-to-market that turned LinkedIn into a lead engine, a curated cohort model that made membership feel earned rather than purchased, and a physical clubhouse experience that gave executives a reason to renew.
By March 2022 they had taken Chief to a $1.1 billion valuation on $140 million raised, faster than nearly any women-founded company in history. Their 2027 challenge is the inverse of their 2019 one: they have to scale past the 20K-member mark without diluting the cohort intimacy and clubhouse exclusivity that made Chief work in the first place, while finally cracking the enterprise B2B channel they have left on the table for six straight years.
1. The Founder Origin Story
Carolyn Childers is the operator half of Chief. She came up through investment banking at Deutsche Bank, then strategy and business development roles at Victoria's Secret and Avon, before landing the formative job of her career: launching Soap.com inside Quidsi and running it as GM through Amazon's acquisition.
From there she went to SVP of Operations at Handy, where she scaled a marketplace, and learned in painful detail what happens when product-market fit drifts away from a stretched team. She has an MBA from Harvard and a finance degree from Boston College, which matters because Chief's pricing power, unit economics, and willingness to sit out the cheap-membership race all bear the fingerprints of someone who can read a P and L.
Lindsay Kaplan is the brand half. She joined Casper as employee number one and ran communications and brand marketing during the years when Casper went from a mattress-in-a-box punchline to a category-defining DTC brand. That experience is the secret weapon Chief shipped with: Kaplan understood, viscerally, how earned media and a strong founder narrative could substitute for a paid acquisition budget in the early innings.
The founding insight, which they have repeated in dozens of interviews, was deceptively simple. Both were senior enough to be mentors but had nowhere to be mentored themselves. Existing women's networks were either too junior, too transactional, or too tied to a single industry.
Their bet was that executive women would pay a five-figure annual fee for a curated peer cohort plus a physical space. The dynamic between them is genuinely complementary in a way most co-founder pairs only pretend to be: Childers runs the operating cadence, Kaplan owns the story, and they appear to have resisted the temptation to step on each other's lanes.
2. What They've Gotten Right
The brand-led go-to-market is the move most founders should be studying. Chief spent almost nothing on paid acquisition in its first three years. Instead Kaplan turned the founder duo themselves into the top of the funnel: Forbes covers, Inc.
Covers, podcast appearances, and a relentless LinkedIn presence from members who got social capital from being seen inside the club. The waitlist hit 40,000 by 2022. That waitlist was itself a marketing asset.
Pricing discipline is the second thing they nailed. Memberships at 5,800 to 7,900 dollars per year priced out the merely curious and signaled scarcity. Most networks would have buckled and run a 999-dollar tier to chase top-line revenue. Childers and Kaplan refused to, and it preserved the cohort quality that made the product work.
The clubhouse strategy was the third moat. By 2023 Chief had physical spaces in New York, Los Angeles, Chicago, San Francisco, and Washington DC. Clubhouses are capital-intensive and operationally hairy, but they did something no Slack group or Zoom cohort could replicate: they gave members a Tuesday afternoon reason to renew.
Soho House figured this out for creatives. Chief figured it out for women operators.
Finally, the personal brand investment. Both founders have become genuinely influential voices on executive women's leadership, which feeds back into the funnel. Their personal brands are now an acquisition channel, a retention tool, and a defense against competitive entry all at once.
3. What They've Gotten Wrong
The real estate over-investment is the most expensive mistake on the balance sheet. Chief signed long-dated leases in five expensive cities right as remote work permanently changed how executives spend their Tuesdays. The April 2023 layoffs were the inevitable consequence: revenue growth slowed, fixed real estate costs did not, and the clubhouses that were a moat in 2022 became an anchor in 2024.
They should have leased flexibly, partnered with existing private clubs, or pursued an asset-light footprint in markets three through five.
Cohort dilution past 20,000 members is the strategic threat they still have not solved. The core product was a curated group of eight to ten women in a cohort with a trained executive coach. That model has a physics problem above 20K members: either you compromise on coach quality, or you compromise on member quality, or you compromise on cohort size.
There is no fourth option, and from member reporting in Fortune and Business Insider it appears all three are happening at once.
The slow B2B enterprise pivot is the missed opportunity that bothers me most. Every Fortune 500 has a budget line for women's leadership development. Chief should have closed enterprise contracts in 2021 and built a sales team in 2022.
Instead they leaned on individual memberships and only began tiering B2B offerings in June 2024, three years late. McKinsey and BetterUp ate that lunch.
The content library is generic. Members pay 6,000 dollars and get programming that often feels indistinguishable from a HBR Ascend subscription. The content moat should have been built years ago.
FAQ
How did Carolyn Childers and Lindsay Kaplan meet? Through a mutual contact in New York in 2018, both senior operators looking for a peer community that did not exist. The conversation turned into Chief's business plan within weeks.
What is each founder's role at Chief in 2027? Childers is CEO and runs operations, finance, and product. Kaplan is Chief Brand Officer, owning brand, comms, and member experience.
Is Chief still profitable after the 2023 layoffs? Chief has not disclosed profitability, but the 2024 tiered relaunch and continued clubhouse presence suggest revenue stabilization. Margin remains pressured by real estate.
Sources
- Carolyn Childers Crunchbase profile
- Lindsay Kaplan Wikipedia
- Chief women's network Wikipedia)
- Inc. - How Chief Became a Billion-Dollar Success Story
- Bessemer Venture Partners - Carolyn Childers profile
- CNBC - Chief expanding amid the pandemic
- Fortune via Yahoo Finance - Chief 5,800-per-year membership critique
- Crain's New York - Lindsay Kaplan 40 Under 40 2022