Network security risk assessment systems and methods are provided. The system has a remote subscriber computer, a risk assessment viewer application, and a risk assessment server that receives a list of software applications operating within the subscriber organization network and a plurality of properties for each of the software applications, and receives a list of organizational nodes within the subscriber organization and a plurality of properties for each of the organizational nodes, determines one or more risk assessment scores and transmits a notification to the remote subscriber computer when a predefined reporting threshold is exceeded.