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of Clearcover and Dearborn Labs to explore why the first wave of digital transformation in insurance may already be outdated.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.

Is the insurance industry stuck in its old ways? In an era where digital media drives brand loyalty and tech reshapes customer expectations, insurance companies might be missing out on huge opportunities. Featured in Feedspot's Top 10 Insurance Podcasts, Kanopi’s Building Tomorrow’s Insurer brings you insights from leaders who are redefining insurance.

In this episode, host and Kanopi CEO Nigel Fellowes-Freeman speaks with Ian White, the force behind Turbo Ventures and MGA Labs. Ian’s decades of experience in insurance and media give him a unique perspective on why insurers need to radically rethink how they connect with customers.

Tune in as Ian challenges traditional approaches and shares eye-opening insights on:

• Why the insurance industry needs media as much as it needs tech
• How legacy mindsets could be losing insurers a digital-savvy customer base
• The untapped potential of AI and content to rebuild trust in insurance
• The insurtech trends no one’s talking about—but should be

For insurance leaders ready to break out of the status quo, this episode offers fresh takes that just might redefine your approach. Don’t miss this discussion with Ian White as he calls out what’s missing—and what’s possible—in the future of insurance.

What does it take to revolutionize the insurance industry while staying grounded in authenticity and purpose? In this episode of Building Tomorrow’s Insurer, host and Kanopi CEO Nigel Fellowes-Freeman sits down with Jeff Shi, founder of Insurtechs.io and a top 50 InsurTech influencer.

Jeff shares his inspiring journey from building a car performance shop in his early days to founding J&J Insurance, where he grew a scratch agency to $27 million in premiums. He brings a wealth of insights on innovation, customer-centric strategies, and the critical role of storytelling in creating trust and brand value in the insurance sector.

Tune in to explore:

• The power of grit and entrepreneurial spirit in building a successful insurance agency
• How storytelling and authenticity are shaping the future of insurance
• The role of AI and technology in redefining customer experience and distribution channels
• Lessons from industry challenges, including managing risks in a rapidly changing environment
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This episode is packed with actionable insights and forward-thinking perspectives for anyone navigating the evolving insurance landscape.

In this episode of Building Tomorrow’s Insurer, host Nigel Fellowes-Freeman dives deep into the evolving world of insurance claims with Sylvia Quang, Head of Claims Solutions for Hong Kong and Macau at Marsh Asia. With an extensive background in law and insurance, Sylvia brings a wealth of experience, having worked across multiple lines of insurance and recognised as one of Australia's Best Lawyers for 2025.

Sylvia shares her fascinating journey from law into the heart of claims management and sheds light on how the claims process is transforming in the digital age. This episode explores critical themes, including:

🔹 The Human Side of Claims: Why claims handling is more than a process—it’s the true test of an insurer's promise.
🔹 Tech in Claims Management: How AI tools, like Marsh Asia’s LED AI, are streamlining processes and enhancing customer service.
🔹 Regulation and Innovation: The contrasting regulatory environments in Australia and Hong Kong and their impact on innovation.
🔹 Catastrophe Management: Preparing for rising claims volumes and training strategies for handling catastrophe-related claims.
🔹 The Future of Claims: Sylvia’s vision for a more efficient, customer-centric claims process and the role of emerging risks like cyber.

Sylvia also touches on the importance of diversity in leadership and how it leads to better decision-making and innovation, especially within claims.

Whether you’re an insurer, a claims professional, or interested in the future of insurance, this episode offers valuable insights into the challenges and opportunities in claims management today.

Tune in to hear Sylvia Quang’s expert perspective on building a better, more empathetic, and technologically advanced claims future.

Featured in Feedspot's Top 10 Insurance Podcasts, Kanopi's latest podcast series 'Building Tomorrow's Insurer' explores the cutting edge of insurtech and digital innovation in the insurance industry. Join host and CEO of Kanopi, Nigel Fellowes-Freeman as he interviews industry leaders and unpacks the latest trends shaping the future of insurance.

In this inspiring episode of Building Tomorrow's Insurer, host Nigel Fellowes-Freeman is joined by Lisa Carter, the highly acclaimed CEO and Managing Director of Clear Insurance. With numerous industry accolades and a passion for transforming the insurance broking landscape, Lisa provides a unique perspective on client-focused risk advice and the future of insurance.

Key themes covered in this episode include:

• The evolution from traditional insurance broking to risk advisory
• Implementing a transparent fee-for-service model in insurance
• The importance of leadership and mentorship in the insurance industry
• Navigating the changing landscape of risk and insurance advice
• The role of technology in simplifying insurance processes
• The vision for a more transparent and client-focused insurance industry

Whether you're an insurance professional, a business owner seeking to understand risk management, or interested in the future of financial services, this episode is a must-listen. Tune in for Lisa Carter's expert insights on revolutionising risk advice and shaping tomorrow's insurer.

Is the insurance industry stuck in its old ways? In an era where digital media drives brand loyalty and tech reshapes customer expectations, insurance companies might be missing out on huge opportunities. Featured in Feedspot's Top 10 Insurance Podcasts, Kanopi’s Building Tomorrow’s Insurer brings you insights from leaders who are redefining insurance.

In this episode, host and Kanopi CEO Nigel Fellowes-Freeman speaks with Michael Waitze, the force behind Michael Waitze Media and Asia Tech Podcast. Michael’s decades of experience in global finance and media give him a unique—and sometimes provocative—perspective on why insurers need to radically rethink how they connect with customers.

Tune in as Michael challenges traditional approaches and shares eye-opening insights on:

• Why the insurance industry needs media as much as it needs tech
• How legacy mindsets could be losing insurers a digital-savvy customer base
• The untapped potential of AI and content to rebuild trust in insurance
• The insurtech trends no one’s talking about—but should be

For insurance leaders ready to break out of the status quo, this episode offers fresh takes that just might redefine your approach. Don’t miss this discussion with Michael Waitze as he calls out what’s missing—and what’s possible—in the future of insurance.

Featured in Feedspot's Top 10 Insurance Podcasts, Kanopi's latest podcast series 'Building tomorrow's insurer' explores the cutting edge of insurtech and digital innovation in the insurance industry. Join host and CEO of Kanopi, Nigel Fellowes-Freeman as he interviews industry leaders and unpacks the latest trends shaping the future of insurance.

In this exciting episode of Building Tomorrow's Insurer, host Nigel Fellowes-Freeman is joined by Anish Sinha, co-founder of upcover, Australia's fastest-growing insurance platform for small businesses. With his background at Goldman Sachs and nearbuy.com, Anish brings a unique perspective on revolutionizing the SME insurance landscape.

Key themes covered in this episode include:

• The journey of building a digital-first insurance platform for SMEs
• Leveraging technology to simplify the insurance buying process
• The role of AI and large language models in shaping the future of insurance
• Balancing innovation with regulatory compliance in insurtech
• The importance of trust and transparency in digital insurance distribution
• Predictions for the commercial insurance industry over the next decade
• Advice for aspiring insurtech founders entering the regulated insurance space

Whether you're an insurtech entrepreneur, an insurance industry professional, or interested in the digital transformation of financial services, this episode offers valuable insights. Tune in to hear Anish Sinha's perspective on building tomorrow's insurer and how upcover is changing the game for small business insurance in Australia.

Featured in ⁠⁠Feedspot's ⁠⁠⁠Top 10 Insurance Podcasts⁠⁠⁠⁠⁠, Kanopi's latest podcast series 'Building tomorrow's insurer' explores the intersection of InsurTech and digital disruption in the insurance industry. Join host and CEO of Kanopi, Nigel Fellowes-Freeman as he interviews industry leaders and unpacks the latest trends shaping the future of insurance.

In this insightful episode, Nigel sits down with Shirin Danesh - Head of Enterprise Agility at Bendigo Bank and Amazon bestselling author of "Level Up: From Unseen to Sought-After." Shirin brings her extensive experience in driving agile transformation across sectors like banking, insurance, and technology.

The conversation delves deep into cultivating the right corporate culture for fostering innovation within large enterprises. Shirin shares her perspectives on the evolution of customer-centric and employee-first mindsets that are shaping modern organizations.

With real-world examples and thought-provoking anecdotes, Shirin unpacks the key pillars for successful culture transformation - from empowering decision-making to effective communication across diverse teams. She also offers insights into overcoming resistance to change and creating environments that support continuous learning.

If you're keen to gain valuable lessons on building community-driven, future-focused organizations primed for sustainable growth, this engaging discussion with the insightful Shirin Danesh is not to be missed.