The purpose of this study is to learn how support brokers (program counselors) carry out and are prepared for their roles in participant-directed programs. More specifically, this study looks at support brokers’ self-perceived roles, training, educational backgrounds, and how well they feel they are prepared for their jobs with Cash and Counseling programs. This study involves two phases of data collection. First, a 20-item survey was sent electronically to support brokers in three states (n = 138) in 2011. Descriptive statistics and t tests were used for the analysis. The second phase involves follow-up telephone interviews (n = 15) with a convenience sample who agreed to participate. Results showed an inconsistency in role definitions and types of training between and within individual states. Moreover, educational backgrounds had a significant influence on the level of support brokers’ perceived preparedness for given tasks. Finally, this study identifies areas that support brokers believe will help improve their performance.