A cloud-based system comprising a processing device, a memory device, and a network interface configured for communication with a user device associated with an enterprise, the memory device storing a risk assessment tool having instructions that, when executed, enable the processing device to:
- detect one or more cybersecurity risk factors associated with the enterprise to determine a risk posture of the enterprise, wherein the one or more cybersecurity risk factors are detected via inline monitoring of encrypted and unencrypted traffic through a cloud-based security system comprising a plurality of distributed enforcement nodes coordinated by a central authority, and wherein the detecting further includes analyzing policy configurations, license status and traffic attributes of the organization to derive multiple risk components;
- attain one or more remediation recommendations for enabling a person associated with the enterprise to select one or more actions for mitigating the one or more cybersecurity risk factors and improving the risk posture of the enterprise, wherein the one or more remediation recommendations are attached by computing a dynamic risk score from the multiple risk components, the multiple risk components comprising at least an external attack surface component, a compromise likelihood component, a lateral propagation component, and a data loss component;
- and
- communicate display information via the network interface to the user device, the display information including at least the one or more cybersecurity risk factors and the one or more remediation recommendations to be exhibited on a Graphical User Interface (GUI) of the user device, wherein the display information is communicated causing the GUI to exhibit a multi-level risk visualization including a high-level dashboard view showing an overall dynamic risk score and risk score trend, and enabling drill-down exploration into contributing factors, entity-specific risk, and prioritized remediation recommendations.