Systems and methods for automatically assessing and monitoring information security effectiveness using collected indicia of sensitive content and indicia of security measure information for a plurality of networked organizational assets/systems to provide respective asset/system value at risk ratings. Elements of the system include automated asset discovery, automated hosting provider and location discovery, collection of information harvested from public sources and, optionally non-public sources, analysis of the collected information against public, non-public, and proprietary sources, and/or mathematical models used to infer broader security program conclusions and to rank asset/system values at risk. Estimates of values at risk are used to prioritize allocation of security measures.