Fitness coaches need to understand the needs of people living with HIV engaged in community-based exercise (CBE) to be competent in developing exercises programs with this population. Our aim was to understand coaches’ experiences engaging in a CBE intervention with PLWH in an urban center in Canada. As part of a broader study, coaches supervised weekly hour-long individualized exercise sessions with PLWH over a six-month period. Using qualitative longitudinal methods, we interviewed coaches up to three times over six months. Transcribed interviews were analyzed cross-sectionally and longitudinally. Seven coaches participated in 15 interviews. Developing confidence, improving health and experiencing a sense of community were viewed as key benefits to PLWH by the coaches. Challenges included accommodating the episodic nature of HIV and ensuring they felt prepared to work with PLWH. Understanding the experiences of coaches engaged in CBE can assist in tailoring exercise programs to meet the needs of PLWH.