Fintech Chatter: Conversations with Fintech CEOs and Founders

Dexter Cousins | Founder, Tier One People
  • 5.0 (2)
  • ENTREPRENEURSHIP
  • UPDATED DAILY

350+ episodes. 40+ countries. The podcast fintech leaders actually listen to. Fintech Chatter is where founders, executives, and investors behind the world's most ambitious fintech companies share what's actually working. We cover topics like raising capital, scaling internationally, hiring leadership teams, and the challenges of building with transformative technologies across payments, crypto, AI, wealth, insurance. If it's in Fintech we've got you covered. Hosted by Dexter Cousins, founder of Tier One People, Australia's specialist executive search firm for fintech and transformative technology.  With 17 years placing CEOs, CTOs, CPO's and country managers across the sector, Dexter brings an operator's lens to every conversation. New episodes biweekly. If you're building, funding, or leading a fintech company - this is your podcast. Follow Dexter on LinkedIn: https://www.linkedin.com/in/dextercousins/ Follow Tier One People: https://www.linkedin.com/company/tier-one-people

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

    4 DAYS AGO

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

    🔥 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. 🔔 SUBSCRIBE for weekly conversations with fintech leaders ⭐️ Give a 5 star review 💬 COMMENT with your thoughts on this episode Send a text Connect on with Dexter Cousins on Linkedin Hire Exceptional Fintech Talent Subscribe on LinkedIn

    47 min
  2. One Million Aus Customers - Matt Baxby, Revolut

    8 FEB

    One Million Aus Customers - Matt Baxby, Revolut

    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 Send a text Connect on with Dexter Cousins on Linkedin Hire Exceptional Fintech Talent Subscribe on LinkedIn

    33 min

  3. 12 JAN

    Networking | Finding Your Next Job In Fintech part 3

    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 introductionsFREE 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: info@tieronepeople.com Connect on with Dexter Cousins on Linkedin Hire Exceptional Fintech Talent Subscribe on LinkedIn

    18 min

  4. 27/11/2025

    Building Your Professional Brand in Fintech

    🚀 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: info@tieronepeople.com Connect on with Dexter Cousins on Linkedin Hire Exceptional Fintech Talent Subscribe on LinkedIn

    15 min

  5. 14/11/2025

    Finding Your Next Role in Fintech - Episode 1

    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 Send a text Contact: info@tieronepeople.com Connect on with Dexter Cousins on Linkedin Hire Exceptional Fintech Talent Subscribe on LinkedIn

    11 min

  6. 10/11/2025

    Weekly Insight: The Silent Crisis of Job Seekers

    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. Send a text Contact: info@tieronepeople.com Connect on with Dexter Cousins on Linkedin Hire Exceptional Fintech Talent Subscribe on LinkedIn

    11 min

  7. 04/11/2025

    Dexter's Weekly Insight - Why Being A Fractional Exec Sucks!

    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? Send a text Contact: info@tieronepeople.com Connect on with Dexter Cousins on Linkedin Hire Exceptional Fintech Talent Subscribe on LinkedIn

    10 min
  8. Where Defi Meets Tradfi - Dan Jowett, OpenMarkets Group

    27/10/2025

    Where Defi Meets Tradfi - Dan Jowett, OpenMarkets Group

    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/ Send a text Contact: info@tieronepeople.com Connect on with Dexter Cousins on Linkedin Hire Exceptional Fintech Talent Subscribe on LinkedIn

    34 min
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350+ episodes. 40+ countries. The podcast fintech leaders actually listen to. Fintech Chatter is where founders, executives, and investors behind the world's most ambitious fintech companies share what's actually working. We cover topics like raising capital, scaling internationally, hiring leadership teams, and the challenges of building with transformative technologies across payments, crypto, AI, wealth, insurance. If it's in Fintech we've got you covered. Hosted by Dexter Cousins, founder of Tier One People, Australia's specialist executive search firm for fintech and transformative technology.  With 17 years placing CEOs, CTOs, CPO's and country managers across the sector, Dexter brings an operator's lens to every conversation. New episodes biweekly. If you're building, funding, or leading a fintech company - this is your podcast. Follow Dexter on LinkedIn: https://www.linkedin.com/in/dextercousins/ Follow Tier One People: https://www.linkedin.com/company/tier-one-people

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