A computer-implemented method is disclosed. The method includes: obtaining, via a server storing a plurality of data records, historical access data in connection with at least one data record; obtaining media engagement data indicating user engagement of media content in connection with the at least one data record; determining a learning content data set associated with the at least one data record based on the historical access data and the media engagement data, the learning content data set including a plurality of media content sets that are associated with defined learning objectives, wherein determining the learning content data set includes: determining a mapping of media content items to the plurality of media content sets; and determining an order associated with the media content sets, detecting one or more trigger conditions associated with the at least one data record; and in response to detecting the one or more trigger conditions: automatically identifying a subset of the learning content data set based on determining a mapping of the one or more trigger conditions to at least one of the defined learning objectives; and generating media recommendation data including the identified subset of the learning content data set.