Who are Carolyn Childers and Lindsay Kaplan — Chief founders profile 2027
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.
TL;DR: Childers and Kaplan are an operator-plus-brand-builder pairing whose Chief execution was elite from 2019 to 2022, sloppy from 2023 to 2025, and now requires a hard pivot to enterprise contracts and digital-first cohorts if they want to defend their unicorn valuation through 2027.
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.
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The Operator + Brand Builder Dynamic
The Childers-Kaplan partnership represents a rare founder pairing where complementary skill sets create a moat that neither could build alone. Childers, who spent her early career at Deutsche Bank before pivoting to operations at Quidsi (the parent company of Diapers.com, later sold to Amazon for $545 million), brought the discipline of building scalable systems from scratch. She then served as Chief Operating Officer at Handy, the home-services platform that raised over $110 million before its acquisition by Angi. Kaplan, meanwhile, was Casper’s first full-time employee and built the mattress startup’s entire brand and communications function from zero to a $1.1 billion IPO filing. Her expertise in narrative control and community-building gave Chief its distinctive voice and the perception of exclusivity that drove early demand. This pairing allowed Chief to avoid the common startup trap of having a charismatic founder with no operational backbone or, conversely, a systems-focused founder who cannot tell a compelling story. By 2027, this dynamic remains critical: Childers must tighten the cost structure and enterprise sales engine, while Kaplan must keep the brand premium and the member experience intimate as the company scales beyond its original clubhouse model.
Chief’s 2023–2025 Turbulence and the Turnaround Imperative
The period between 2023 and 2025 was arguably the most challenging for Chief since its founding. The company faced a series of high-profile layoffs, cutting roughly 13% of its workforce in early 2024, and saw its valuation come under pressure as the broader tech market corrected. Membership growth slowed from the explosive triple-digit percentages of 2020–2022 to single-digit annual growth by 2025, with churn rates increasing among members who felt the in-person clubhouse experience had become too crowded and less intimate. The company’s attempt to launch a digital-only membership tier in 2023 met with mixed reception, as existing members questioned whether the virtual offering diluted the brand’s core value proposition. By 2025, Chief had also failed to secure a single major Fortune 500 enterprise contract, leaving its revenue heavily reliant on individual memberships at $5,000 to $10,000 per year. The 2027 challenge, therefore, is not merely about growth but about rebuilding trust with both members and investors. Childers and Kaplan must demonstrate that they can execute a disciplined turnaround: cutting non-core costs, re-investing in the highest-value physical locations, and finally landing the enterprise deals that would provide recurring, predictable revenue streams.
The 2027 Enterprise B2B Pivot and Cohort Evolution
The single most important strategic lever for Chief in 2027 is the enterprise B2B channel, which the founders have acknowledged they “left on the table” for six years. Unlike individual memberships, enterprise contracts offer multi-year commitments, higher average revenue per account, and lower churn rates. To crack this channel, Chief needs to package its cohort-based leadership programs as a corporate benefit that companies can offer to their senior female executives—similar to how companies subsidize executive coaching or MBA programs. This requires building a dedicated enterprise sales team, developing ROI measurement tools that HR departments can use to justify the expense, and creating tiered pricing that scales from 10-seat packages to 500-seat deployments. Simultaneously, Chief must evolve its cohort model to accommodate a larger, more geographically dispersed membership. The original model of 10–12 women meeting monthly in a physical clubhouse is difficult to scale beyond 20,000 members. By 2027, expect to see Chief experimenting with hybrid cohorts that combine quarterly in-person gatherings with monthly virtual sessions, as well as topic-specific cohorts (e.g., “Women in Fintech,” “Chiefs of Staff”) that allow members to self-select into smaller, more relevant sub-communities. This evolution will test whether the founders can maintain the intimacy that made Chief valuable while achieving the scale required to justify its unicorn valuation.
FAQ
What exactly does Chief do for its members? Chief connects senior women executives through curated peer cohorts, private clubhouses in major cities, and leadership development programming. Members typically join to access a trusted network of women at the same career level, with the goal of sharing strategic advice, business opportunities, and support they can't get inside their own organizations.
How much does a Chief membership cost, and is it worth it? Annual membership fees have ranged from roughly $5,000 to $10,000 depending on location and tier, with some corporate-sponsored plans covering the cost. Whether it's worth it depends on how actively a member uses the cohorts and events—many report strong ROI from business referrals and career moves, while others find the value diminishes if they don't engage regularly.
Who is eligible to join Chief? Chief targets women in senior leadership roles—typically VPs, C-suite executives, and partners at major companies or firms. The application process includes a review of title, company size, and professional experience, and acceptance is not automatic; the curated model is designed to maintain a high-caliber peer group.
How did Chief grow so fast from 2019 to 2022? The founders combined a strong brand narrative (women supporting women at the top) with a savvy LinkedIn-based lead generation strategy that made membership feel exclusive and desirable. They also raised substantial venture capital—over $140 million by early 2022—which funded rapid expansion of clubhouses and team hiring, pushing the valuation past $1 billion.
What went wrong for Chief between 2023 and 2025? The company struggled with post-pandemic shifts in work patterns, slower membership growth, and the challenge of maintaining cohort intimacy while scaling. Some members reported diluted experiences, and the enterprise B2B channel—which could have provided stable revenue—remained underdeveloped, leading to layoffs and a reassessment of strategy.
What is Chief's biggest challenge in 2027? The core tension is scaling beyond roughly 20,000 members without losing the exclusive, high-touch feel that made the network valuable. The founders must finally build a strong enterprise sales channel to secure multi-year corporate contracts, while also keeping individual members engaged enough to renew at premium prices.
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