The purpose of this study was to investigate the experiences and perspectives of community health workers (CHWs), supervisors, and leadership of the CHW program at Kansas City CARE. In addition to a short demographic survey, we conducted semi-structured, in-person interviews with 17 individuals, ranging from 34 minutes to 90 minutes over a period of 3 weeks between March 23, 2017 and April 12, 2017. Interviews included questions about current work experiences, career motivation and aspirations, training and development experiences, and organizational dynamics. Interviews with supervisors and leadership included additional questions about broader organizational and supervision topics. The semi-structured nature of the interviews allowed us to draw comparisons while simultaneously capturing unique information from each respondent.