Resilience in the age of agentic AI

In this episode, host and Cloudflare Field CIO Khalid Kark sits down with Jonathan Jaffe, CISO of Lemonade, to discuss a paradigm shift in cybersecurity: the move from traditional "backup-and-recovery" resilience to agentic security.

As AI-enabled threats become more relentless, Jaffe argues that human-centric security operations can no longer keep pace. He explains how Lemonade is pioneering the use of "platoons" of autonomous AI agents to handle everything from real-time threat intelligence ingestion to automated code reviews and vulnerability patching.

Learn more about the insights discussed in this episode within our 2026 Cloudflare Security Signals Report .

Participants:

Khalid Kark is a globally recognized technology strategist and Field CIO at Cloudflare, where he works closely with C-suite leaders and board members to shape secure, scalable, and resilient digital strategies. With over two decades of experience at the forefront of technology leadership, Khalid helps organizations navigate the complex intersection of business innovation, cybersecurity, and enterprise transformation. Previously, Khalid led Forrester’s Security & Risk and Technology Leadership practices and served as Global Managing Director of Deloitte’s Technology Leadership Program and chaired Deloitte’s Tech Eminence Council to elevate thought leadership in AI, cybersecurity, and digital innovation. 

Jonathan Jaffe is the CISO at Lemonade Insurance where he oversees the security of engineering, strategy, product, and operations of an AI-native InsureTech disruptor. With 25+ years of technical experience in security roles, his expertise spans a variety of security domains. He is a prolific adopter of, and advisor to, innovative security start-ups. Jonathan is also a cybersecurity and privacy attorney who understands legal risk and regulation.