Cybersecurity management is a sociotechnical problem comprising organisational knowledge management of humans and technology. Focusing on risk and incident management, we present our approach for enhancing cybersecurity awareness in organisations and ecosystems. By augmenting our cybersecurity awareness platform with human-in-the-loop anomaly detection and machine learning, we are able to handle the dynamics of organisational human activity, as well as the continuous developments in the cybersecurity domain. We illustrate the potential impact of our approach with a realistic example in the healthcare context