Fintech Chatter: Conversations with Fintech Leaders
Fintech Chatter: Conversations with Fintech Leaders
Dexter Cousins | Founder, Tier One People
Checkbox AI CEO: $23M Series A After 9 Years Bootstrapping
47 minutes Posted Feb 22, 2026 at 7:00 pm.
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🔥 We find the 1% who redefine what's possible - Executive search for fintech → https://tieronepeople.com Checkbox AI just raised $23M at $100M valuation serving enterprise customers SAP, PepsiCo, Telstra, and Woolworths. CEO Evan Wong shares the 9-year journey from bootstrapped startup to enterprise legal AI platform, competing against $5B+ valuation businesses like Harvey. 📊 KEY METRICS: • US$23M Series A at $100M valuation (total of US$29m raised) • 100+ enterprise customers including Fortu...