Human-centric cyber security incidents remain a significant concern for organizations of all sizes, especially in the post-pandemic shift to remote and hybrid work. Existing strategies for addressing these issues, such as communication-based approaches, often fail to engage end users effectively or assess their knowledge adequately. This paper introduces CyberTrack, a flexible tool designed to enhance end-user engagement and compliance by integrating gamification, rewards, and monitoring mechanisms. Grounded in foundational security knowledge domains, CyberTrack enables organizations to assess security maturity, monitor user engagement, and address individual training needs. By fostering a culture of security consciousness, this approach promotes resilience against cyber threats, equipping organizations to tackle human-centric challenges comprehensively and proactively. The discussion presents the merits of a multi-faceted approach to promote, engage, and to monitor compliance where organizations can holistically embed training and education as part of their security strategy.