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In this pilot study, we sought to understand employer perspectives on hiring young applicants, especially applicants who have been involved in the juvenile justice system. A survey was conducted to assess employers’ perceptions of qualities young applicants often lack, what qualities they are seeking, and the skills, training, and/ or documents that would be beneficial for young applicants during the hiring process. The survey was deployed to 19 employers; 12 employers responded. Six employers who completed the survey also took part in follow-up interviews. In the interviews, employers expounded on how job and career preparation programs can best prepare youth for successful employment, how their companies approach hiring candidates with juvenile records, and how STEM (science, technology, engineering, and mathematics) skills are incorporated into entry level positions. Through both the survey and interview, employers also shared how the COVID-19 pandemic impacted their hiring processes.