Cybersecurity awareness training (CAT) should be adaptable to the evolving cyber threat landscape, cost effective, and integrated well with other components. Unfortunately, few CAT systems can satisfy those requirements.This presentation introduces a new smart model for conducting cybersecurity trainings based on ML/AI with three main goals: (1) training efforts are initiated by emerging relevant threats and delivered first to the most vulnerable members; (2) training results must be able to provide actionable intelligence to be employed by enterprise risk management, enterprise threat intelligence, and other systems; and (3) the CAT system must be effective and affordable.