A system for deriving a rating representative of a level of cybersecurity of a user is configured to execute steps of a method comprising requesting, from the user, identifying information about the user; requesting, from the user, input in response to a set of predetermined questions provided to the user based on the identifying information about the user; collecting, based on at least the identifying information, public domain data about the user and data from the user's digital assets; and computing, based on the collected data and the input to the set of predetermined questions provided by the user, a numerical value defining the cybersecurity rating.