Chief is losing the B2B enterprise tier to BetterUp and McKinsey — the 2027 budget reality

Direct Answer

Chief should have pivoted to B2B enterprise — selling to companies for women's leadership development at $50-200K/yr per account — by 2024. Instead, leadership stayed loyal to the individual-membership thesis that built the brand, and the enterprise budget got eaten elsewhere. BetterUp now sits at roughly $1B+ ARR with a women-leadership product line and 750+ enterprise logos.

McKinsey's Connected Leaders Academy runs structured cohorts (the public-facing programs are subsidized, but the parallel paid enterprise cohorts price at roughly $25-50K per seat). Egon Zehnder's Women on Boards franchise has quietly become a $40M+ practice. By the time Chief launched a real enterprise SKU in late 2025, the 2026 and 2027 HR budgets were already committed.

The window to recover the F500 women-leadership wallet is closing — probably 12-18 months before the category locks in around BetterUp + a consultancy partner.

1. The Enterprise Budget Landscape

The market Chief should have owned is well-documented and very large. Across the Fortune 500, women-leadership development is a roughly $3B annual category — a blend of cohort programs, coaching subscriptions, sponsorship initiatives, and board-readiness pipelines funded out of HR, Talent, and DEI lines.

The buyer is almost never the participant. It's the CHRO, the Chief Talent Officer, or — for board-track programs — the General Counsel.

BetterUp is the runaway category leader on platform spend. Public reporting and the company's own claims of trust by 750+ enterprises put platform ARR in the $1B range, with women-leadership and emerging-leader pipelines as a meaningful and visible portion. The Anheuser-Busch InBev partnership — a global pilot built around women across 18 countries — is the template every HR team now references.

BetterUp wins because it sells a platform (unlimited coaching + AI + analytics) that fits inside an HR procurement process the buyer already understands.

McKinsey Connected Leaders Academy is the prestige play. CLA's branded "free" cohorts for diverse leaders are subsidized loss-leaders, but the practice they pull through — bespoke leadership academies for paying enterprise clients — runs at roughly $25-50K per seat in cohorts of 30-60.

Five years in, McKinsey has built a multi-thousand-alumna network that doubles as a referral engine into their consulting practice. That is a moat Chief cannot replicate.

Egon Zehnder's Women on Boards programs operate at the top of the funnel — sub-CEO leaders preparing for first or second board seats. The price is opaque (engagement-based, often bundled with search), but the practice clears $40M+ per year and converts directly into search fees worth multiples more.

Yale, GW Center for Excellence in Public Leadership, and Wharton round out the boutique academy tier with $15-30K open-enrollment seats that HR departments fund without negotiation.

Chief is not on this map in any material way. Public estimates put enterprise revenue under $10M — perhaps 3% of where it should be at this stage.

2. Why Chief Didn't Win This Battle

The individual-membership thesis is the original sin. Chief built the brand by selling $5-8K personal memberships to senior women — the buyer was the participant, the value prop was peer community, the GTM was Instagram and word-of-mouth. That thesis worked beautifully for the first $100M in revenue and made the company a cultural object.

It also made enterprise sales structurally hard. A CHRO doesn't buy individual memberships in bulk because the program doesn't have the artifacts she needs — no cohort curriculum, no learning analytics, no HRIS integration, no L&D credit framework. The product was designed for the wrong buyer.

The GTM compounded the mistake. Chief never built a real HR-buyer outbound motion — no field sales team carrying F500 HR quotas, no procurement playbook, no MSA template that survives a Fortune 100 legal review. Through 2023 and 2024, the founders publicly leaned into community and brand storytelling while BetterUp's enterprise reps were closing seven-figure deals against the same logos.

Founder focus is the third failure. Public-facing energy went into clubhouse design, media coverage, and the magazine — all good consumer marketing, none of it solving the enterprise wedge. By the time the late-2024 B2B pivot was announced, BetterUp had two more years of platform maturity and McKinsey had two more cohort cycles of alumni.

Now Chief is playing catch-up against incumbents with installed bases, procurement relationships, and CHRO trust they don't have to rebuild. Every quarter of delay compounds — the F500 HR budget cycle locks 18 months in advance, which means missing 2026 budget season effectively forfeits 2027 enterprise revenue.

The cohort effect makes it worse: once 200 of the Fortune 500 have standardized on BetterUp + a consulting partner for women-leadership programs, the remaining 300 follow because procurement teams benchmark against peers. That tipping point is roughly 9-12 months out based on current adoption curves.

3. What Chief Should Build in 2027

The playbook is unsentimental. Build an Enterprise tier priced $50-200K/yr per account, with sliding scale by employee count and number of cohorts. Bundle a curated curriculum, a dedicated CSM, learning analytics, and HRIS-grade reporting. Stop selling seats; start selling programs.

Hire an HR-buyer outbound team — 15-20 enterprise AEs with CHRO Rolodexes, paired with SDRs and a sales engineer who can speak L&D ops. This is a $15M annual investment that needs to be made now or never.

Launch co-branded "Chief for [Company]" employee chapters. Let the buyer skin the program with their logo, run it inside their walls, and report on it to their board. This is what BetterUp can't easily do — Chief's brand is the moat here, not the product.

Stop competing with BetterUp on individual coaching. Chief will lose. Coaching is a feature, not a wedge. Partner with BetterUp or a coaching marketplace for the 1:1 layer and focus product investment on cohort facilitation, peer matching, and content — the things the community brand actually earned.

FAQ

Is Chief actually losing money or just growing slower? Both — layoffs in 2024 and 2025 plus flat individual-membership growth suggest the consumer thesis has plateaued while the enterprise tier hasn't replaced it.

Could Chief just sell? Possibly to a BetterUp or Skillsoft as a brand acquisition, but the multiple would punish current investors versus where the round was raised.

What's the one move that matters most? Hiring a CRO with F500 HR-tech enterprise scars — everything else is downstream.

Sources

• HR Dive — Anheuser-Busch InBev, BetterUp brew women-focused leadership program
• BetterUp — Leadership Development Training & Coaching for Teams
• Josh Bersin — BetterUp Manage: Pioneering AI-Powered Platform For Leaders
• McKinsey — Connected Leaders Academy overview
• McKinsey — Insights into leadership building: Five years of Connected Leaders Academy
• Hacking the Case Interview — McKinsey Academy: Programs, Cost, and What to Know
• Yale SOM — Women's Leadership Program
• GW CEPL — Executive Women's Leadership Program