
Checkbox AI CEO: $23M Series A After 9 Years Bootstrapping
From Fintech Chatter: Conversations with Fintech CEOs and Founders by Dexter Cousins | Founder, Tier One People
February 22, 2026 · 48 min · Episode 362
About this episode
Evan Wong discusses Checkbox AI's journey from bootstrapped startup to raising $23M in Series A funding.
🔥 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...
People in this episode
Host: Dexter Cousins
Guest: Evan Wong
Topics covered
- funding
- bootstrapping
- enterprise AI
- fintech
- startup journey
Keywords
- Checkbox AI
- Evan Wong
- Series A
- bootstrapping
- enterprise customers
- fintech
Mentioned in this episode
Organizations: Checkbox AI, SAP, PepsiCo, Telstra, Woolworths, Harvey
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