How do we scale a deeper level of security awareness training without sacrificing efficacy? This talk will explore strategies and tactics for developing security education based on employees' roles, access, and attack surface while designing not only for efficiency but also for effectiveness. By prioritizing the highest-risk teams, pooling teams to collaboratively threat-model, and contextualizing universal truths of security hygiene to those threat models, we can deliver training that leverages employees' roles, fosters retention via active participation, and eases the burden on trainers within the security team. Attendees will walk away with a roadmap for building scalable, contextual, and collaborative role-based employee security education within their organizations.