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

from Fintech Chatter: Conversations with Fintech CEOs and Founders · host Dexter Cousins | Founder, Tier One People

🔥 We find the 1% who redefine what's possible - Executive search for fintech → https://tieronepeople.comCheckbox 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 Journey02:26 Understanding Checkbox AI's Role in Legal Tech06:27 The Evolution of No-Code and AI in Legal Solutions10:50 Navigating the Competitive Landscape of Legal AI12:58 The Importance of Customer-Centric Product Development18:49 Building for Enterprise: Lessons Learned25:58 Scaling Efficiently in the Age of AI28:38 Embracing an AI-First Mindset31:19 Navigating Fear and Shame in Entrepreneurship35:09 Advice for Young Entrepreneurs39:51 Finding Energy and Passion in Work40:52 Building a Resilient Organization44:23 Future Plans and Growth Strategies🔗 EVAN WONG:LinkedIn: https://www.linkedin.com/in/theevanwongCheckbox 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📺 ABOUT FINTECH CHATTER:Australia's leading fintech podcast with 350+ episodes reaching 30,000+ fintech professionals in 40 countries monthly.🔔 SUBSCRIBE for weekly conversations with fintech leaders⭐️ Give a 5 star review💬 COMMENT with your thoughts on this episodeSend us Fan MailContact: [email protected] on with Dexter Cousins on LinkedinHire Exceptional Fintech TalentSubscribe on LinkedIn

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This episode was published on February 22, 2026.

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