The “Smart Job Application Assistant” is developed as a solution to the growing burden of the job market. The system is a web-based application that helps students streamline the job search and application process. The model automates resume parsing and job matching by extracting and analyzing user resume content. A multi-label regression classifier has been used to classify the jobs with the user resumes as references. To extend this work, an analysis of the multi-label logistic regression model as well as a RoBERTa model has been done. This analysis led to the discovery that the logistic regression model is better suited to the problem statement. Further, the system can align the users’ qualifications with job requirements for precise matches through the Sentence Transformer model. Developed based on real-world testing and collaboration, the “Smart Job Application Assistant” serves as a valuable tool for students to ease their job application journey.