KeyCaliber applies data science to cybersecurity stack data to identify mission-critical assets so cybersecurity executives can focus specifically on what matters most by through a better allocation of resources, devise roadmaps, and articulation the value of their cybersecurity programs. The technology brings a new and innovative approach to old procedures. It is a technological shift to automation and machine learning because that is what produces the results that security leaders need to handle today’s challenges. KeyCaliber then automatically computes the risk to these mission-critical assets, shows the cybersecurity technologies applied to these assets as controls, and enables the building of scenarios modeling how increasing/decreasing controls impacts risk.