The problem
People chasing a job, school or AI skills can't find vetted experts, and companies can't upskill staff on AI fast
What they do
Marketplace for career, admissions and AI coaching, plus AI upskilling programs for companies
Traction Eight-figure revenue, cash-flow positive pre-A; 35,000+ reviews; 2,000+ coaches
Hiring trend
- Open roles
- 8
- Ops roles
- 2
- Headcount
- ~160-320
Flat: LinkedIn ~324 (-2% YoY, incl. contractors); Revelio 161 staff (+14% YoY); 8 staff roles plus 184 coach listings
Hiring in
- Leland - Lehi
- Remote (US)
Latest news
Jun 2026
Rebranded as 'home for ambition' and launched leland.ai for business AI upskilling ↗Glassdoor
3.2 ★ 5 reviews ↗Funding
- Last round
- $12M
- Stage
- Series A
- Date
- Nov 2024
Led by Forerunner Ventures
- Hiring+18 open roles on the live job board (3–9 roles = +1)
- Funding recency+0.5Series A · $12M, Nov 2024 (23 months ago): 12–24 months = +0.5
- Traction+0.75Some growth: Eight-figure revenue, cash-flow positive pre-A; 35,000+ reviews; 2,000+ coaches
- Red flags0None found in the last 24 months
- Total2.251 + 0.5 + 0.75 − 0 = 2.25 → Warm-up
Seed rule: a Series A of $15M or less without strong traction starts in Warm-up whatever the score (Steady by score alone).
Distance (10K) is a separate read on how long the lead can last. It doesn't change the score.
Distance
10K · edge: grows with users
A leading premium coaching marketplace with real two-sided liquidity (35k+ reviews, eight-figure revenue), but career coaching is crowded and AI tutors and agents threaten the core; the B2B AI-training pivot is months old.
Sources: Consumer Startups: Leland $10M+/yr coaching marketplace playbook (Jul 2025) ↗ · Leland: Becomes the home for ambition, leland.ai launch (Jun 2026) ↗
Last checked Oct 14, 2026