A system and method may identify the best matching entities using artificial intelligence, by for example determining, from a set of features describing a number of entities, a subset of features which when input to a machine learning module allow the machine learning module to match a pair of entities based on the ability of the second entity in the pair to successfully take over responsibilities handled by the first entity in the pair; training a machine learning module using the determined features; and for a first entity described by the determined set of features, using the machine learning module to determine a list of entities matching the first entity, each entity in the list of entities associated with a matching score.