This empirical study examines the complex dynamics influencing the effectiveness and performance of Compliance Officers (COs) within Cypriot organizations. With a focus on exploring the relationships between jurisdictional complexities, industry-specific regulations, organizational size, professional experience, Artificial intelligence-based tools, and readiness to technology adoption, this research employs a comprehensive approach to shed light on the multifaceted factors shaping CO roles. Leveraging a structural equation modelling framework, data was collected through a questionnaire survey administered to COs across diverse sectors. The results indicate that industry-specific regulations, organizational size, and professional experience significantly impact CO effectiveness, while the mediating role of AI-based tools and the moderating influence of technology adoption further enhance these relationships. The findings contribute to both theoretical knowledge and practical implications, offering insights for organizations and policymakers to optimize compliance efforts. While acknowledging limitations, this study lays the foundation for a deeper understanding of CO roles in the contemporary regulatory landscape.