Checkbox AI CEO: $23M Series A After 9 Years Bootstrapping

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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