A system and method assesses and manages risk of an operation of a user. A rules engine of computer executable instructions stored in the storage device determines at least one of a safety risk measurement based on key performance indicators, an operational safety risk measurement for the operation as a function of the operational safety risk measurement information stored in a storage device and/or a conditional safety risk measurement for the operation as a function of the conditional safety risk measurement information stored in the storage device. A processor connected to the storage device executes the rules engine. An output interface connected to the processor indicates the determined safety risk for the operation.