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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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Tier One People placed Matt Baxby as Revolut Australia's founding CEO. Six years later: 1M customers, profitable. The right leader changes everything. Looking for your next hire? Contact Dexter Cousins for a confidential discussion.

Welcome back to Fintech Chatter Podcast - In our first episode of 2026 Matt Baxby reveals how Revolut reached 1M customers and saved Australians $250M in FX fees while achieving profitability. Discover the hiring secrets, growth strategy, and vision to become Australia's #1 finance app.

Chapters
00:00 Introduction and Milestone Achievements
06:45 New Products
12:08 Banking License Update
14:06 Why Revolut has outlasted other Neobanks
16:37 6 Years at Revolut, One Million Customers.
20:09 What makes someone successful at Revolut?
24:46 Why Revolut's "work from anywhere" policy works.
28:04 What's next for Revolut?
31:33 Careers at Revolut

Links
Revolut Careers: revolut.com/careers

Revolut Australia: revolut.com/en-AU

Discuss Hiring: tieronepeople.com/contact

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Most people treat networking like fitness - they lie on the sofa for three years, then panic when they're out of shape. In this episode, Dexter Cousins breaks down the 95-5 principle: 95% of your job hunting success comes from 5% of your network. Learn how to identify the critical 5% of your network, activate them strategically, and turn two-minute conversations into warm introductions. This is networking done right.

KEY TAKEAWAYS

• The 95-5 Principle: Focus on your critical 5%, not broadcasting to thousands
• T1/T2/T3 Framework: How to filter your network strategically
• The Two-Minute Ask: Why small requests get bigger results
• Compounding: How one conversation generates 1-2 warm introductions
• The Trust Shortcut: Borrow credibility through warm introductions

FREE DOWNLOAD

Network Activation Worksheet - Get your T1/T2/T3 filter template, email scripts, and conversation guide. https://tieronepeople.com/wp-content/uploads/2026/01/Network_Activation_Worksheet-1.pdf

ABOUT THE HOST

Dexter Cousins is Managing Director of Tier One People, the executive search firm for Fintech. With 25+ years in recruitment, Dexter has an unmatched record helping fintech companies build exceptional leadership teams.

NEXT EPISODE

Episode 4: The Interview - How to interview like you're diagnosing their business, not begging for a job.

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