Fintech Chatter: Conversations with Fintech Leaders

🔥 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:

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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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🚀 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

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Thinking about your next career move in 2026? Maybe you're actively hunting for your next role in Fintech?

This is Episode 1 of a 5-part series that completely flips the script on job hunting in fintech. Whether you're looking for a permanent role or exploring fractional opportunities, this approach will transform your entire career conversation.

Most job seekers approach their career transition completely backwards. They ask the wrong questions, compete on the wrong battlefield, and leave millions in untapped value on the table. This episode introduces the framework that transforms you from "Please hire me" to "Here's the problem I solve. Here's why you'd be crazy not to talk to me."

We break down:
- Why conventional job hunting is fundamentally broken
- The questions you should be asking instead
- How to identify the concrete problems you solve
- The Career Balance Sheet framework
- Real-world examples of value creation ($1.5M, $20M+, +40% revenue growth)
- Why this framework makes you remarkably hireable

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In this episode, Dexter discusses the silent crisis affecting job seekers, highlighting the alarming rates of burnout and mental health issues before employment. 

He explores the current job market landscape, the challenges candidates face, and the impact of financial stress on mental health. 

Takeaways

• Two-thirds of job seekers are experiencing burnout.
• The average job hunt takes almost six months.
• Job seekers send an average of 294 applications before landing a job.
• Financial stress and mental health are intertwined issues.
• Over 70% of employers research candidates on social media.
• 82% of employees are at risk of burnout in 2025.
• Gen Z and millennials report peak burnout at just 25 years old.
• Financial pressure is the top concern for young Australians.
• Candidates may exhibit odd behavior due to stress.
• Understanding candidates' contexts is crucial in recruitment.

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Dexter Cousins brings a new weekly insight on Fintech careers and hiring.

In this episode he explores the growing trend of C-suite professionals contemplating a shift from their current roles to alternatives that better support their well-being. 

While at the same time executives who have made the shift by becoming self-employed or starting Fractional service offerings, are seeking permanent work again.

Let s know what you think. What has been your experience in either offering Fractional Exec services or using them?

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In this episode of Fintech Chatter, host Dexter Cousins speaks with Dan Jowett, CEO of OpenMarkets Group, about the rapid convergence of Tradfi and DeFi

About OpenMarkets Group

Power your Fintech, Advisory, or Trading business with an end-to-end Wealth Management and Trading solutions. 

Openmarkets empowers financial institutions and advisers to deliver a seamless investment experience to their clients. They provide a comprehensive suite of trading, clearing and settlement, custody, and technology solutions that enable businesses to efficiently manage portfolios, scale their business, and support investors in achieving their financial objectives.

About This Episode

Tune in as Dan and Dexter discuss how OpenMarkets has transformed from a traditional stockbroker to a technology-focused fintech, the regulatory hurdles facing the crypto industry, and the future of equities trading in a rapidly changing environment.

Chapters

00:00 Introduction to OpenMarkets and Fintech Landscape
02:26 Evolution of OpenMarkets: From Stockbroker to Tech Innovator
06:08 Navigating the Future: DeFi and Traditional Finance
11:45 Regulatory Challenges and Opportunities in Digital Assets
15:37 Building a Strong Culture at OpenMarkets
18:47 Navigating Market Changes in Fintech
21:07 Lessons from Leadership During Challenging Times
23:22 The Importance of Networking and Global Perspectives
24:26 The Future of DeFi and Regulatory Challenges
27:24 Cultivating a Positive Workplace Culture
30:59 Finding the Right Fit in a Dynamic Environment

Find Out More - https://openmarkets.com.au/

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In this episode of Fintech Chatter, host Dexter Cousins speaks with Joni Pirovich, a crypto compliance expert and founder of Crystal AOS. They discuss Joni's journey from being a crypto lawyer to a tech founder, the challenges of hiring in the compliance space, and the role of AI in enhancing productivity and filling the compliance knowledge gap in the digital assets space. 

Joni and Dexter chat about the current state of play in the crypto industry in Australia, regulatory challenges, and the need for holistic policy to foster innovation in the tech sector.

Chapters

00:00 Introduction to Fintech Chatter and Guest Background
04:50 The Evolution of Compliance in Crypto
09:24 AI's Role in Enhancing Compliance and Legal Practices
14:11 Challenges in the Australian Crypto Landscape
18:43 The Need for Holistic Regulatory Approaches
23:18 Building a Supportive Ecosystem for Startups
27:56 Conclusion and Future Outlook

Contact Joni: [email protected] 

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Is Ethereum the layer to exchange value via the internet? 

In this episode of Fintech Chatter, host Dexter Cousins speaks with Jake Denny, Chief Commercial Officer of Pier Two, about Ethereum staking and its commercial potential.

Tune in for a discussion on the differences between Ethereum, Bitcoin, and Solana, the future of money through smart contracts, and the real world use cases that are being delivered through stablecoin adoption.

Find out more - https://piertwo.com/

Chapters

00:00 Introduction 
01:28 Understanding Ethereum Staking and Its Commercial Potential
07:00 The Use Cases of Ethereum vs. Bitcoin and Solana
13:05 The Future of Money and the Role of Smart Contracts
18:55 The Impact of Technology on Traditional Finance
24:51 The Importance of Speed in Financial Transactions
31:07 The Role of Curiosity and Hustle in Fintech Careers
39:19 Pier Two's Mission and Vision in the Crypto Space
56:24 Connecting DeFi and TradFi: Opportunities for Collaboration

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