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Explore strategies for developing effective role-based security awareness training in this 33-minute LASCON conference talk. Learn how to prioritize high-risk teams, conduct collaborative threat modeling, and contextualize security hygiene principles to create scalable and impactful employee education programs. Discover methods to leverage employees' roles, foster active participation, and reduce the burden on security trainers. Gain insights into building a roadmap for implementing contextual and collaborative security education within organizations, addressing scaling challenges and pain points along the way.