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Lemonade's Jonathan Jaffe on Trading Feedback for Security Technology

Jonathan Jaffe, CISO at Lemonade, has built what he predicts will be "the perfect AI system" using agent orchestration to automate vulnerability management at machine speed, eliminating the developer burden of false positive security alerts. His unconventional approach to security combines lessons learned from practicing law against major tech companies with a systematic strategy for partnering with security startups to access cutting-edge technology years before competitors.

Jonathan tells David a story that showcases how even well-intentioned people will exploit systems if they believe they…

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