The federal government has established rapid identification, linkage, and engagement in medical care of HIV-positive individuals as a high priority. Outreach workers and other linkage coordinators are identified as key personnel in implementing this policy. Young racial/ethnic minority men who have sex with men (MSM) have relatively high and growing rates of HIV infection and would benefit from the services of outreach workers. In this article, we describe the characteristics of outreach workers employed by eight demonstration sites participating in the federal Special Projects of National Significance (SPNS) Young MSM of Color Initiative, the linkage and retention models used by the sites, and the number of outreach/ linkage contacts and individuals referred to HIV care. We summarize rates of retention of outreach workers in employment, factors associated with worker turnover, and costs associated with their replacement. We also summarize the experiences of demonstration sites in employing and retaining outreach workers and improving their performance. The insights of outreach workers are reported regarding the challenges they experienced while conducting outreach. Recommendations from demonstration site project managers and outreach workers are offered to improve workplace performance and job retention. Outreach and retention strategies, as well as lessons learned in employing outreach workers, are useful to programs serving young racial/ethnic minority MSM and other HIV-positive groups.