Abstract: A web platform hosting job postings uses a machine learning-driven approach to update user profile information for matching job postings with qualified job seekers. The web platform determines a job posting to serve to a job seeker device and, using a machine learning model trained to contextually evaluate job seeker user profile information against job postings, determines a high priority job qualification of the job posting that is missing from the user profile information. A representation that the job qualification is missing from the user profile information and a prompt asking whether the job seeker meets the job qualification are output within a job feed that includes information of the job posting. The web platform outputs an updated presentation of the job posting to the job seeker device to indicate, based on input obtained in response to the prompt, whether the job seeker is qualified for the job posting.