The three proactive security principles of visibility, prioritization, and remediation have always been the foundation of vulnerability management teams. But these teams face continuous challenges. To address these challenges, this report breaks down the six questions that need to be answered for each proactive security principle: who, what, when, where, why, and how. The introduction of generative AI (genAI) into proactive security promises to provide a broader and speedier ability to answer these questions, providing further opportunities for the proactive security market to grow.