Freight transportation continues to expand in volume and complexity. However, many organizations are still struggling to balance operational efficiency with strict regulatory compliance and safe driving practices. Against the growing challenges with safety risks, numerous evolving standards, and the growing influence of data analytics in the logistics industry, this study investigates how freight operators can systematically strengthen their safety culture, regulatory compliance and driver performance across varying operational conditions. This research examines the interaction between compliance management frameworks, driver behaviour, monitoring technologies, and organisational safety policies to identify those interventions that ultimately improve overall freight safety outcomes. Combining analysis of policies, field observations and performance data from selected freight companies, this study identifies long-standing gaps in compliance implementation including inconsistent training delivery, fragmented reporting mechanisms and a limited utilization of telematics for proactive risk detection. Findings indicate that the most substantial gains in regulatory compliance and driver behavior arise from not merely having safety-and-compliance tools available, but the extent to which organizations institutionalize them. Companies that embeded telematics data into day-to-day decision-making as opposed to treating it as a surveillance mechanism found drivers becoming more engaged and proactive in self-correcting risky behaviors. Similarly, when coaching programs moved from punitive models to collaborative data supported feedback loops, drivers demonstrated greater situational awareness and greater consistency in following safety protocols. The study concludes that strengthening safety and compliance of freight operations requires a concerted approach that takes technology, policy and human factors into account. This research provides practical insights for freight operators, regulators and policymakers seeking evidence-based approaches to increase compliance and improve safety performance across the freight transportation ecosystem.