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Fintech Chatter: Conversations with Fintech CEOs and Founders

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Fintech Chatter: Conversations with Fintech CEOs and Founders

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

February 23, 2026 • Dexter Cousins | Founder, Tier One People • Episode 362

0:00 | 47:21

🔥 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 Fortune 500

• Capital Raise will be used to expand into the US market

• Named in Gartner's 2025 Hype Cycle for Legal Tech

• 9-year journey from founding to Series A

⏱️ CHAPTERS:

00:00 Introduction to Checkbox AI and Its Journey

02:26 Understanding Checkbox AI's Role in Legal Tech

06:27 The Evolution of No-Code and AI in Legal Solutions

10:50 Navigating the Competitive Landscape of Legal AI

12:58 The Importance of Customer-Centric Product Development