Technologies for using an inferred relationship between data sets to computationally align the data sets and generate actionable output include obtaining, from an online system, a set of member records; inferring a job category based at least partly on job function data extracted from the set of member records; obtaining, from the management system, a set of job records that correspond to the inferred job category; calculating an aggregate alignment score by comparing member skills data extracted from the set of member records to job skills data extracted from the set of job records, where the aggregate alignment score is a measure of a mismatch between the member skills data for the set of member records and the job skills data for the set of job records; based on the aggregate alignment score, identifying a skill that is actionable to address the mismatch between the member skills data and the job skills data; generating actionable output that replaces, modifies, or supplements first course recommendation data that does not map to the identified skill with second course recommendation data that maps to the identified skill.