The identification of safety hazards and risks and their associated control measures provides the foundation for any safety program and essentially determines the scope, content and complexity of an effective occupational health and safety management system. In the case of work-related road safety (WRRS), there is a gap within current knowledge, research and practice regarding the holistic assessment of WRRS safety systems and practice. In order to mitigate this gap, a multi-level process tool for assessing WRRS safety systems was developed from extensive consultation, practice and informed by theoretical models and frameworks. Data collection for the Organisational Driving Safety Systems Analysis (ODSSA) tool utilised a case study methodology and included multiple information sources: such as documents, archival records, interviews, direct observations, participant observations, and physical artefacts. Previous trials and application of the ODSSA has indicated that the tool is applicable to a wide range of organisational fleet environments and settings. This paper reports on the research results and effectiveness of the ODSSA tool to assess WRRS systems across a large organisation that recently underwent considerable organisational change, including amalgamation of multiple organisations. The outcomes of this project identified considerable differences in the degree by which the organisation addressed WRRS across their vehicle fleet operations and provided guidelines for improving organisations’ WRRS systems. The ODSSA tool was pivotal in determining WRRS system deficiencies and provided a platform to inform mitigation and improvement strategies.