Fintech Chatter: Conversations with Fintech CEOs and Founders

Block Just Cut 4,000 Jobs. WiseTech Cut 2,000. Here's What To Do Next.
Last week was a wake-up call for anyone working in fintech and tech in Australia.
Block — the company behind Square, Cash App, and Afterpay — cut more than 4,000 employees. That's nearly half the company, down from over 10,000 to just under 6,000. The stock surged 24% on the same day. Afterpay is still headquartered in Sydney, and Australian staff have been directly affected.
The same week, WiseTech Global announced 2,000 job cuts over two years — 29% of their workforce. CBA quietly cut 300 roles, mostly in technology. All three cited AI as the driver.
In this video, Dexter Cousins breaks down what actually happened and gives you three practical steps to take today if you've been affected or think you might be next.

Chapters
00:00 Navigating Job Loss in FinTech
01:39 How Your Experience Is In Greater Demand Than Ever
03:02 Avoid Three BIG Mistakes
03:49 Career Balance Sheet
05:03 Identifying Opportunities
05:45 GTM Strategy — Quick Wins
07:09 Building Momentum and Networking
Career Balance Sheet - https://drive.google.com/file/d/1hLJJQl2B_h1u00G46sNxlhGNRXXZlCv6/view
Part 1 - https://tieronepeople.com/2025/11/14/find-fintech-jobs/
Part 2 -https://tieronepeople.com/2026/01/12/professional-networks-job-hunting/
Part 3 - https://tieronepeople.com/2026/02/16/professional-brand-first-principles/
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🔥 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
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

📺 ABOUT FINTECH CHATTER:
Australia's leading fintech podcast with 350+ episodes reaching 30,000+ fintech professionals in 40 countries monthly.

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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.

Send a text
Contact: [email protected]
Connect on with Dexter Cousins on Linkedin
Hire Exceptional Fintech Talent
Subscribe on LinkedIn

🚀 Hire outstanding Fintech talent - https://tieronepeople.com
✅ Follow Dexter on Linkedin - https://www.linkedin.com/in/dextercousins/
⬇️ Download the worksheet - https://drive.google.com/file/d/1rkcgAsabfYtPrZw1owzg1BpsnUxvLCDR/view?usp=sharing

In this episode of FinTech Chatter, Dexter Cousins shares insights on how to find your next role in the fintech industry using the Lean Startup methodology. He emphasizes the importance of creating a career balance sheet, identifying problem customers, and positioning oneself as an expert before applying for jobs. Dexter provides practical steps to research and validate hypotheses about companies' needs, turning job hunting into a targeted and strategic process.

00:00 Creating Your Professional Brand
06:24 Leveraging Top Brands
07:42 Finding Target Companies
08:31 Organizing Your Research
10:42 Iterating Your Approach
12:02 The Importance of Precision in Job Applications
Send a text
Contact: [email protected]
Connect on with Dexter Cousins on Linkedin
Hire Exceptional Fintech Talent
Subscribe on LinkedIn