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The increasing cost of college often drives students with financial need to use federal work-study programs to meet part of their financial obligations. Few work-study programs exist that focus on enriching students’ professional skills through relevant work experiences. Researchers are calling for reevaluation of programs funded by federal work-study funds to address the current needs of students. This study explored the impact of one innovative program that provided work-study students and their supervisors professional development focused on career-readiness preparation. Findings included practices that built engagement, confidence, and skills for both supervisors and students, while building a community of support that facilitated maximization of the benefits of the work-study program.