Abstract: A computer-implemented method for evaluating cybersecurity risk may include (i) identifying telemetry data collected from endpoints of an entity, (ii) calculating a cybersecurity risk score for the entity by searching the telemetry data for information indicative of cybersecurity risk exposure of the entity and performing an actuarial analysis on the information indicative of the cybersecurity risk exposure to quantize a potential consequence of the cybersecurity risk exposure, and (iii) performing, based on the cybersecurity risk score, a security action to protect the entity from the potential consequence of the cybersecurity risk exposure. Various other methods, systems, and computer-readable media are also disclosed.