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What does it actually take to win in the Canadian market? In Episode 50 of Building Tomorrow's Insurer, Nigel Fellowes-Freeman sits down with Finn Magee, CEO of Insurtech Canada, to talk about a market that looks a lot like Australia's on paper but rewards a very different playbook. Finn explains why he rebuilt Insurtech Canada as a for-profit organisation, what he looks for before he'll introduce a startup to carriers, and why he's raising a fund to keep Canadian insurtech capital in Canada. They also get into: Why fraud has become a top priority for carriers, and how they're trying to get ahead of itHow worsening nat cat events are changing the way insurers model and manage riskPractical tips for getting it right before entering the Canadian marketBuilding Tomorrow's Insurer is Kanopi's podcast for insurance, fintech and digital distribution leaders.

Most insurers are asking how to add AI to existing workflows. Kyle Nakatsuji thinks that's the wrong question. In this episode of Building Tomorrow's Insurer, Nigel Fellowes-Freeman sits down with the founder of Clearcover and Dearborn Labs to explore why the first wave of digital transformation in insurance may already be outdated. After spending a decade building one of the world's best-known tech-native insurers, Kyle believes Agentic AI is forcing the industry to rethink everything from claims and underwriting to operating models and core systems. Together they discuss: • Why even modern insurers may need rebuilding for the AI era • The difference between automation and agentic systems • Why many AI initiatives stall between pilot and production • The future of headless insurance platforms • How AI changes the economics of underwriting and claims operations • Whether insurers should build proprietary AI workflows or rely on vendors • Why context, judgement and human relationships still matter • The future of embedded insurance in an AI-native world If you're a CEO, CIO, COO, Chief Claims Officer or transformation leader trying to understand what insurance operations could look like over the next five years, this conversation provides a practical look at what's changing now. Topics: Agentic AI in insurance, insurance digital transformation, AI claims automation, insurance operations, insurtech innovation, embedded insurance, AI underwriting, future of insurance technology, Clearcover, Dearborn Labs.

Everyone in financial services is being told to move faster on AI. Boards want innovation. Teams want automation. Regulators want stronger governance. The problem is that most organisations are trying to balance all three at the same time. In this episode of Building Tomorrow’s Insurer, Nigel Fellowes-Freeman sits down with Davy Ek, a senior leader with more than 20 years’ experience across operational transformation, governance and regulatory reform in financial services. Together, they unpack one of the biggest tensions emerging in the Agentic AI era: How do organisations embrace increasingly autonomous systems without creating risks they can’t fully explain, govern or control? The conversation explores: why so many organisations remain stuck between AI experimentation and operational readinesshow boards are thinking about oversight and accountabilitywhether governance frameworks can realistically keep pace with AI capability growththe risks leaders may still be underestimatingand why operational resilience, trust and decision-making discipline matter more than ever.This episode is not about AI hype. It’s about what happens when highly regulated industries collide with technology evolving faster than their operating models were designed to absorb. #AI #AgenticAI #FinancialServices #Insurance #OperationalRisk #Governance #DigitalTransformation

Why do insurance executives keep funding AI pilots that never reach production — and what does it actually take to break the cycle?In this episode of Building Tomorrow's Insurer, host and Kanopi CEO Nigel Fellowes-Freeman sits down with James Benham, Founder and CEO of JBK and Terra, to diagnose the structural reasons AI transformation stalls in insurance organisations and what it takes to move from proof of concept to full-scale deployment.James brings 25 years of insurance technology experience to the conversation, having built bespoke systems for carriers, TPAs, MGAs, brokers, and ancillary providers since 2004. As CEO of both JBK — a full-service insurance technology consultancy — and Terra, a workers' compensation platform, James has sat at the executive table with insurers across the US implementing machine learning, workflow automation, and agentic AI at scale.Key themes covered in this episode:- Why insurers have always lived in Groundhog Day — and why AI is finally forcing them out of it- The CEO-COO-CIO trifecta: why misaligned leadership is the single biggest reason pilots die- Agentic AI versus RPA: what actually changes when you put a high-IQ brain on top of a workflow engine- Data, process, and tooling: which comes first in a real AI transformation roadmap- The metrics that matter — combined ratio, claim load per adjuster, underwriting throughput — and how to set them without accelerating the wrong outcomes- Why dedicated automation teams, not side-of-desk innovation, are the only path to productionEssential listening for insurance CXOs, CIOs, and transformation leaders who are tired of the pilot loop and ready to act.

What does it actually take to embed financial services into a platform? In this episode of Building Tomorrow’s Insurer, Nigel sits down with Michael Nuciforo, founder of Thriday (now part of Tyro), to explore how fintech platforms are reshaping distribution by owning the customer workflow. This is not a conversation about theory. It’s about execution. Michael shares how platforms like Thriday integrate banking, accounting, and financial services into a single experience for small businesses — and what that means for insurers looking to participate in embedded ecosystems. In this episode, we cover: Why workflow ownership is more important than product innovationHow embedded finance shifts from add-ons to core infrastructureWhat insurers often misunderstand about platform economicsHow to evaluate embedded partnerships from a fintech perspectiveThe operational reality of integrating financial products into live platformsWhat makes an embedded model commercially viableHow platforms think about trust, customer experience, and monetisationIf you’re a leader in insurance, fintech, or digital distribution, this episode provides a clear view into how platforms are redefining where and how financial products are delivered.

When a single virus can wipe out computers worldwide in 24 hours, who picks up the pieces? Meena Wahi, Australia's first cyber insurance broker and founder of Cyber & Data Risk Managers, reveals how the cyber insurance landscape has evolved since 2013—and where it's headed next. From the CrowdStrike outage that shocked boards worldwide to the fragmented nature of supply chain risk, Meena breaks down why cyber resilience isn't just a buzzword and how specialist insurers are winning the market share battle. She shares eye-opening insights from ASX 200 boardrooms, explains why Australian regulators might be too "benign," and predicts the convergence of cybersecurity and insurance. Whether you're a startup founder wondering if cyber insurance is worth it or a director trying to understand your organization's risk exposure, this conversation demystifies one of the fastest-evolving sectors in insurance. Host Nigel Fellowes-Freaman asks the questions everyone wants answered but few dare to ask. Timestamps • 00:00 - Introduction to cyber insurance and today's guest • 02:15 - Meena's background: MBA at Monash, consulting at Pricewaterhouse • 03:15 - The origin story: Researching privacy legislation and discovering cyber insurance • 04:05 - Getting invited to New York, meeting with AIG and Chubb • 04:35 - Becoming Australia's first cyber insurance broker in 2013 • 05:30 - Evolution of the cyber insurance market over the past decade • 06:20 - London market perspective: CFC's leadership and market share battles • 07:45 - How cyber wording has evolved globally and locally • 08:50 - The role of specialist MGAs: Emergence, CFC, Coalition • 09:20 - Why only specialists will survive in cyber insurance • 10:30 - The aggregated risk problem: 1,000 claims in one day scenario • 11:45 - 2017 statistic: 4 billion data breaches and $500M in claims • 12:30 - Key changes in cyber policy coverage and trends • 13:45 - Supply chain risk has increased dramatically • 14:30 - The fragmented nature of internet risk and liability ownership • 16:05 - IT supply chain partners and contingent business interruption coverage • 17:20 - CPS 230/234 impact on technology vendors and value chains • 18:45 - How prudential standards are driving demand for cyber insurance • 19:45 - Why Australian regulators are 'benign and friendly' compared to the US • 21:10 - Will increased regulatory oversight aid or hinder innovation? • 22:15 - The board perspective: Generational gaps and skill matrix • 23:15 - Key insights from ASX 200 AGMs and boardroom conversations • 24:20 - The information flow problem: Board oversight vs operational reality • 25:40 - What is cyber resilience? Breaking down the buzzword • 27:00 - Cyber resilience as risk acceptance and resourcefulness • 28:30 - Recovery timeframes: Hours vs months • 29:10 - The CrowdStrike outage: What it revealed • 29:45 - Outage vs cyber incident: Why definitions matter for coverage • 30:45 - Are we prepared for the next global cyber incident? • 31:30 - Educating startups and SMEs about cyber insurance • 32:40 - The implementation challenge: Cybersecurity maturity levels • 33:20 - Difference between education and training • 34:00 - Affordability challenges for small businesses • 34:45 - The underinsurance problem: $250K extensions on PI policies • 35:30 - Future trends: Convergence of cybersecurity and insurance • 36:10 - Warranty insurance from cybersecurity providers • 36:45 - The need for better collaboration and feedback mechanisms • 37:30 - Customization of cyber insurance policies • 38:15 - Fun question: Unconventional insurance ideas • 39:00 - The concept of subscription cyber insurance with bank accounts • 39:50 - Final thoughts and wrap-up

Are you still trying to figure out if agentic AI is hype or reality? Alex Taylor, Global Head of Emerging Technology at QBE Ventures, cuts through the noise in this no-nonsense conversation about what's actually working in insurance AI - and what's failing spectacularly. Discover why agentic AI isn't just "fancy RPA," how insurers are running shadow mode tests to prove AI can outperform human underwriters, and why the real barrier isn't technology, it's data strategy. Alex shares jaw-dropping examples from software development (27-hour autonomous coding sprints!) and explains how insurers are moving from chatbot failures to genuine operational transformation. Key insights: the difference between vibe coding and provable AI, why observability matters more than accuracy, Microsoft-Allstate's governance playbook, and the one thing every insurance CIO must do in the next 30 days. If you're responsible for AI strategy, digital transformation, or innovation in insurance, this episode delivers the practical framework you've been missing. No vendor pitches. Just real talk about implementation, regulation, partnerships, and what separates AI winners from the FOMO-driven crowd. Timestamps 0:00 - Introduction - Alex Taylor & QBE Ventures 1:30 - The shift from 'what's possible' to 'what works' in insurance AI 2:15 - Why insurers underinvested in technology (and why it made sense) 3:45 - The real problems insurers are trying to solve with emerging tech 5:00 - Internal pressures: cost, complexity, and competitive speed 6:20 - Customer expectations and the value proposition (spoiler: they don't care about AI) 7:30 - What actually changed in the last 12-18 months 8:30 - Agentic AI explained: beyond classical generative AI 9:45 - The critical difference between agentic AI and RPA 11:20 - The operating system experiment: 27 hours of autonomous coding 13:00 - Inversion of control: humans as engineering managers 14:30 - Build vs buy vs partner: how the calculation has changed 16:15 - What the ideal tech stack looks like: people, process, tech, governance 17:45 - The regulatory complexity and governance requirements 18:30 - Snorkel's AI leaderboards and model certification 19:45 - Case study: What didn't work (the chatbot mistake 99% made) 21:30 - What actually works: agents as employees, not buttons 22:15 - Metrics that matter: measuring AI against human baselines 23:30 - Shadow mode testing: running parallel systems for 12 months 25:00 - Partnership models: how CVCs accelerate experimentation 26:30 - QBE's Lighthouse Program: 3-week proof of value 27:45 - Cutting through the hype: what's real vs. overstated 28:45 - The one thing to do in the next 30 days: know where your data is 30:00 - Closing thoughts and where to follow Alex's content

As insurers look ahead to 2026, one question looms large: how do you stay trusted, relevant, and competitive in a world shaped by platforms, AI, and rising customer expectations? In this standout end-of-year episode of Building Tomorrow’s Insurer, Kanopi Founder & CEO Nigel Fellowes-Freeman is joined by Emma Fawcett, CEO of Compare Club - Australia’s largest independent comparison platform. Emma brings a rare perspective shaped by leadership roles at MYOB, News Corp, and now the centre of insurance distribution. Together, they explore what insurers can learn from platforms that sit closest to customer decision-making. This conversation dives into: Why value matters more than price in modern insurance How comparison platforms are reshaping trust, advice, and distribution The role of data and AI in delivering personalisation without crossing the “creepy” line Where insurers are missing opportunities across claims, complaints, and lifecycle moments How partnerships, ecosystems, and comparators can fuel smarter product design What agentic AI really means for insurers, and where human expertise still matters most If you’re thinking about customer experience, platform partnerships, AI adoption, or the future of insurance distribution, this is a must-listen conversation to close out the year.

Payments might be the least glamorous part of insurance — but they’re one of the most powerful levers for customer experience, efficiency, and competitive advantage. In this episode of Building Tomorrow’s Insurer, Nigel Fellowes-Freeman sits down with Ed Wiley (Head of Growth, Monoova) and David Greene (Chief Commercial Officer, Monoova) to unpack one of the most overlooked transformation opportunities in insurance: how money actually moves. Monoova’s team has spent decades reshaping payment infrastructure across industries. Today, they break down what insurers need to know — and what they can learn from more advanced sectors like e-commerce, utilities, and cross-border payments. In this episode: Why insurance payments are “stuck in the ’90s” How real-time payments (NPP & PayTo) unlock instant customer delight The hidden cost of direct debit — and why BECS deprecation makes change unavoidable What e-commerce can teach insurers about conversion and checkout journeys Automating reconciliation: the 5% problem that drives 95% of customer complaints How partners can help insurers modernise without multi-year transformation The future of payments: ubiquity, automation, and AI-enabled money movement Whether you’re an insurer, an underwriter, or an insurtech founder — this episode gives you a clear view of where payments are heading, and why the next five years will redefine how premiums and claims flow.

What happens when you build one of Asia’s most successful digital insurers—then decide to start over? In this episode of Building Tomorrow’s Insurer, Walter de Oude, Founder and CEO of Chocolate Finance (and previously Founder of Singlife), joins Kanopi CEO Nigel Fellowes-Freeman for an honest conversation about risk, reinvention, and the blurry lines between banking, insurance, and asset management. Walter shares his journey from actuary to founder, including: The hard-won lessons of launching Singapore Life from scratch Why branding and customer trust can be a company’s strongest assets How he’s now building Chocolate Finance, a capital-light model for smarter, happier money What the future of financial ecosystems might look like as banks, insurers, and asset managers converge This one’s for anyone fascinated by where finance goes next—and what it takes to build something truly new.

How do you grow a business fast—without losing what made it special? In this episode of Building Tomorrow’s Insurer, host and Kanopi CEO Nigel Fellowes-Freeman sits down with Katie Stranaghan, Head of Financial Lines at High Street Underwriting Agency, to explore how High Street scaled from a small family business to one of Australia’s leading underwriting agencies while keeping people and culture at the core. Katie shares her journey from joining High Street straight out of school to helping shape its next chapter of growth, technology, and leadership. Tune in as she discusses: Building technology that enhances—not replaces—human connection Maintaining authenticity during rapid expansion How culture drives customer experience The next evolution of underwriting and broker partnerships For anyone scaling a business or leading through change, this episode is packed with lessons on staying grounded while moving fast.

Underwriting agencies are evolving fast — balancing growth, culture, and technology while staying relevant to brokers and customers. In this episode of Building Tomorrow’s Insurer, host and Kanopi CEO Nigel Fellowes-Freeman sits down with Marc Crossman, Executive GM of Distribution and Strategy at UAA Group, to unpack what it takes to lead transformation in today’s market. Tune in as Marc shares: Why distribution strategy is shifting from visibility to value How UAA is embedding tech and culture to drive transformation Lessons from leading teams across Australia and Singapore The future role of underwriting agencies in insurance For leaders navigating change and growth in underwriting, this episode is a must-listen.

How do insurers balance innovation with an ever-tightening web of regulation? In this episode, host Nigel Fellowes-Freeman sits down with award-winning litigator and regulatory specialist Kezia David to unpack the forces reshaping insurance in Australia and beyond. Kezia shares: Why ASIC’s crackdown is changing every stage of the policy lifecycle The biggest blind spots insurers still face—and how to address them How innovation and compliance can (and must) work together What startups need to know to avoid regulatory pitfalls Why proactive, customer-first approaches to Nat Cat events matter more than ever A sharp, timely conversation for anyone navigating the next wave of accountability and customer expectation in insurance.

Insurance for small businesses has always been complex, expensive, and underserved. But what if technology and partnerships could change that? In this episode of Building Tomorrow’s Insurer, host Nigel Fellowes-Freeman sits down with Eric Mignot, Founder and Chairman of +Simple, to explore how one of Europe’s most ambitious digital brokers is reshaping SME insurance. From CFO at Suez, to leading Hiscox, to launching +Simple, Eric’s journey shows how insights from telecoms, utilities, and digital banking inspired him to reinvent insurance distribution. Tune in to hear: Why expense ratios—not loss ratios—are the real challenge in SME insurance How +Simple scaled to 14,000 brokers across five countries The role of technology in simplifying underwriting, claims, and accounting Why programmatic M&A and capacity pooling became game-changers Eric’s lessons on raising capital, partnering smartly, and scaling across Europe This is a must-listen for anyone building insurtech, rethinking distribution, or leading digital transformation in insurance.

Insurance policies aren’t just complex - they’re overwhelming. For brokers, underwriters, and customers alike, navigating thousands of pages of wording can feel like an impossible task. In this episode of Building Tomorrow’s Insurer, host Nigel Fellowes-Freeman sits down with Jasmin Flori-Hess, Co-Founder of Raindrop, to explore how her startup is tackling one of insurance’s most overlooked challenges: policy complexity. From Switzerland to Darwin, Jasmin shares her journey from corporate communications and change management to founding an insurtech powered by AI, machine learning, and natural language processing. Raindrop is on a mission to make policy wordings clearer, compliance more accurate, and the customer experience more transparent. Tune in to hear: Why policy complexity is one of the industry’s biggest risks—and opportunities How Raindrop builds AI pipelines trained by insurance experts, not just generic models The role of trust, accuracy, and explainability in insurance AI What a future of hyper-personalised, customer-first insurance could look like If you’re a broker, underwriter, or insurtech builder, this episode is packed with insight into how AI can simplify the most complex part of insurance.