Fintech Chatter: Conversations with Fintech CEOs and Founders

David Hyman co-founded Lendi Group in 2013 and built it into Australia's largest non-bank mortgage platform with a $107 billion loan book, 5 million customers, and $350 million in annual revenue. He stepped down as CEO in January 2026 and within weeks was building his next company.In his fourth appearance on Fintech Chatter, David joins Dexter to talk about Mono AI, a platform business that helps established companies become AI native before a leaner AI native competitor makes them irrelevant.They cover the difference between human motion and agentic motion, why the CTO is often the biggest blocker to AI strategy, what ElevenLabs's $2 million revenue per employee tells you about the next three years, and the two traits (curiosity and high agency) that separate people who will thrive in this transition from those who won't.David also explains the Mono AI wedge model, why he's building a global AI business from Sydney, and what roles the company is actively hiring for now.This episode was recorded just before the major job losses at Block and Atlassian. It is one of the most practically important conversations on this show to date.Find David on LinkedIn or visit monoai.coTier One People: tieronepeople.comSend us Fan MailConnect on with Dexter Cousins on LinkedinHire Exceptional Fintech TalentSubscribe on LinkedIn

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.Chapters00:00 Navigating Job Loss in FinTech01:39 How Your Experience Is In Greater Demand Than Ever03:02 Avoid Three BIG Mistakes03:49 Career Balance Sheet05:03 Identifying Opportunities05:45 GTM Strategy — Quick Wins07:09 Building Momentum and NetworkingCareer Balance Sheet - https://drive.google.com/file/d/1hLJJQl2B_h1u00G46sNxlhGNRXXZlCv6/viewPart 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/Send us Fan MailContact: info@tieronepeople.comConnect on with Dexter Cousins on LinkedinHire Exceptional Fintech TalentSubscribe on LinkedIn

🔥 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 MailConnect on with Dexter Cousins on LinkedinHire Exceptional Fintech TalentSubscribe on LinkedIn

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.Chapters00:00 Introduction and Milestone Achievements06:45 New Products12:08 Banking License Update14:06 Why Revolut has outlasted other Neobanks16:37 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 RevolutLinksRevolut Careers: revolut.com/careersRevolut Australia: revolut.com/en-AUDiscuss Hiring: tieronepeople.com/contactSend us Fan MailConnect on with Dexter Cousins on LinkedinHire Exceptional Fintech TalentSubscribe on LinkedIn

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 TAKEAWAYSThe 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 DOWNLOADNetwork 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.pdfABOUT THE HOSTDexter 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 EPISODEEpisode 4: The Interview - How to interview like you're diagnosing their business, not begging for a job.Send us Fan MailContact: info@tieronepeople.comConnect on with Dexter Cousins on LinkedinHire Exceptional Fintech TalentSubscribe 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=sharingIn 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 Brand06:24 Leveraging Top Brands07:42 Finding Target Companies08:31 Organizing Your Research10:42 Iterating Your Approach12:02 The Importance of Precision in Job ApplicationsSend us Fan MailContact: info@tieronepeople.comConnect on with Dexter Cousins on LinkedinHire Exceptional Fintech TalentSubscribe on LinkedIn

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 hireableSend us Fan MailContact: info@tieronepeople.comConnect on with Dexter Cousins on LinkedinHire Exceptional Fintech TalentSubscribe on LinkedIn

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. TakeawaysTwo-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 us Fan MailContact: info@tieronepeople.comConnect on with Dexter Cousins on LinkedinHire Exceptional Fintech TalentSubscribe on LinkedIn

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 us Fan MailContact: info@tieronepeople.comConnect on with Dexter Cousins on LinkedinHire Exceptional Fintech TalentSubscribe on LinkedIn

In this episode of Fintech Chatter, host Dexter Cousins speaks with Dan Jowett, CEO of OpenMarkets Group, about the rapid convergence of Tradfi and DeFiAbout OpenMarkets GroupPower 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 EpisodeTune 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.Chapters00:00 Introduction to OpenMarkets and Fintech Landscape02:26 Evolution of OpenMarkets: From Stockbroker to Tech Innovator06:08 Navigating the Future: DeFi and Traditional Finance11:45 Regulatory Challenges and Opportunities in Digital Assets15:37 Building a Strong Culture at OpenMarkets18:47 Navigating Market Changes in Fintech21:07 Lessons from Leadership During Challenging Times23:22 The Importance of Networking and Global Perspectives24:26 The Future of DeFi and Regulatory Challenges27:24 Cultivating a Positive Workplace Culture30:59 Finding the Right Fit in a Dynamic EnvironmentFind Out More - https://openmarkets.com.au/Send us Fan MailContact: info@tieronepeople.comConnect on with Dexter Cousins on LinkedinHire Exceptional Fintech TalentSubscribe on LinkedIn