ft. Ben Dulieu, CIO & Chief Information Security Officer, Duck Creek Technologies
Just as Duck Creek announced its acquisition of Send Technology Solutions – an AI-native underwriting orchestration engine behind more than $26 billion in Gross Written Premium. In this conversation, CISO Ben Dulieu explains the thinking behind the move: why agentic insurance only delivers real ROI when AI is embedded into core operational workflows, not bolted on from the periphery. He breaks down the orchestration layer making these agents auditable and compliant at scale, and doesn’t hold back on the industry’s real problem – two years of pilots and proof of concepts with almost nothing to show for it. His take? The biggest risk to insurance right now is being too afraid of risk to take the leap.
ft. Garry Kasparov, Chess Grand Master
In 1997, Garry Kasparov lost to Deep Blue. It was headline news around the world. But what the headlines missed was what he did next. Instead of fighting the machine, he started thinking about how to work with it – and that shift changed everything. In this conversation, Kasparov brings three decades of human-vs-AI thinking to the insurance industry: why the leaders who rely too heavily on computers will lose, why those who ignore them will lose too, and why the only winning move is finding the right collaboration between human intuition and machine power.
ft. Nancy Bewlay, EVP & Global Chief Underwriting Officer, AIG
Recorded before her appointment as AIG’s Executive Vice President and Global Chief Underwriting Officer, this conversation with Nancy Bewlay hits differently now. With over 30 years in underwriting across Swiss Re, C.V. Starr, and AXA Group, Nancy breaks down how the world’s most disciplined underwriters think about climate risk, AI, and portfolio strategy in a market that never stops moving. Her take? AI is an asset – but curiosity is still the most important underwriting skill.
ft. Luisa Barile, Group CEO, ManyPets
Claims costs down. Customer trust up. At the same time. Louisa Barile, CEO of Many Pets, breaks down how over half of their claims are now processed with zero human touch – and why 100% automation was never the goal. From AI agents talking to each other behind the scenes, to the MCP-first infrastructure bet they’re making right now, this is a candid look at what scaling an AI-native insurer actually looks like. The kind of closed-door conversation you’d want a seat at.
ft. Stu Spencer, Group CMO, AIA
Stu Spencer, Group CMO of AIA, sits down with Rory Pyke, Vice President at Insurtech Insights, for a candid conversation on innovation, strategy, and the future of Hong Kong’s largest insurer. Discover how Stu balances internal priorities with external market demands to keep AIA at the forefront of insurance innovation.
ft. Sarah Griffin (Jacobs), SVP Product, Nationwide
Consumer trust in insurance is slipping. Sarah Jacobs, SVP Product at Nationwide, has spent 25 years inside the industry and isn’t shying away from the hard questions: where is money being left on the table, why does fraud get quietly accepted as a cost of doing business, and what would it take for insurers and customers to actually trust each other? From building codes to AI-powered roof inspections, this is a candid look at what rebuilding trust really requires.
ft. Ericson Chan, Group Chief Information & Digital Officer, Zurich
AI is meant to make insurance smarter. So why is 90% of AI investment delivering almost no return?
Ericson Chan, Group Chief Information & Digital Officer at Zurich, joins us to unpack why AI adoption is a leadership problem, not a technology one – and why the leaders who get it right are the ones willing to get their hands dirty. From the STAR framework for accountable AI to why jobs aren’t disappearing but workflows are, this is the kind of closed-door conversation you’d want a seat at.
