In our latest CIO ASEAN Leadership Live session, I - Estelle Quek, Editorial Director of CSO ASEAN engaged Violet Chung, Senior Partner at McKinsey, on how artificial intelligence (AI) and generative AI (GenAI) are reshaping the insurance sector across Southeast Asia. Our conversation was structured around key questions that CIOs and senior technology leaders must address to move from experimentation to enterprise transformation. We began by asking what explains Southeast Asia’s relatively low AI maturity scores, despite its digital readiness. Chung pointed to the need for holistic transformation-beyond technology procurement, emphasizing leadership alignment, change management, and scalable enterprise capabilities. As embedded insurance gains traction, we asked how insurers should evolve their business models. Chung highlighted the importance of agile partnerships with non-financial players and the co-creation of customer-centric value propositions. On GenAI, we explored what lessons CIOs can draw from early pilots. Chung cautioned that many initiatives lack integration and measurable ROI. She stressed the importance of infrastructure flexibility, workforce enablement, and a clear roadmap for scaling. I also asked how insurers should approach AI governance, particularly in underwriting and customer-facing applications. Chung advocated for embedding compliance from the design phase, maintaining human oversight, and ensuring data transparency. Finally, we examined the readiness of insurers to scale GenAI amid legacy systems and siloed data. Chung recommended infrastructure-agnostic platforms and agentic architectures, supported by public-private collaboration to close protection gaps and accelerate innovation.