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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

18:49 Building for Enterprise: Lessons Learned

25:58 Scaling Efficiently in the Age of AI

28:38 Embracing an AI-First Mindset

31:19 Navigating Fear and Shame in Entrepreneurship

35:09 Advice for Young Entrepreneurs

39:51 Finding Energy and Passion in Work

40:52 Building a Resilient Organization

44:23 Future Plans and Growth Strategies

🔗 EVAN WONG:

LinkedIn: https://www.linkedin.com/in/theevanwong

Checkbox AI: https://www.checkbox.ai

📰 EPISODE SOURCES:

Checkbox Series A Announcement: https://www.checkbox.ai/news/checkbox-raises-23-million-series-a-to-become-the-front-door-for-in-house-legal-teams

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