Building Tomorrow's Insurer

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 it How worsening nat cat events are changing the way insurers model and manage risk Practical tips for getting it right before entering the Canadian market Building 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of Clearcover and Dearborn Labs to explore why the first wave of digital transformation in insurance may already be outdated.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 readiness how boards are thinking about oversight and accountability whether governance frameworks can realistically keep pace with AI capability growth the risks leaders may still be underestimating and 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 innovation How embedded finance shifts from add-ons to core infrastructure What insurers often misunderstand about platform economics How to evaluate embedded partnerships from a fintech perspective The operational reality of integrating financial products into live platforms What makes an embedded model commercially viable How platforms think about trust, customer experience, and monetisation If 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.