ESL programs at post-secondary institutions must often generate revenue in addition to teaching students English. Institutions often impose explicit expectations on these programs to generate profit, creating unique challenges for those who administer them. This qualitative case study investigated challenges faced by ESL program directors at one university in Canada. Semistructured interviews were used to collect data from program directors (N = 3) on topics relating to administration, marketing, the mandate to generate revenue, and the complexities of ESL program legitimacy and marginalization in higher education contexts. Five key themes emerged from the data: (a) the necessity for directors to be highly qualified and multilingual, as well as have international experience; (b) a general lack of training, support, and resources for program directors; (c) institutional barriers such as working with marketers and recruiters with little knowledge of ESL contexts; (d) program fragmentation and marginalization on campus; and (e) reluctance to share information and program protectionism. Findings point to the need for increased training and support for ESL program directors, along with the need for institutions to elevate the profile of these programs so they are not viewed as having less value than other academic programs on campus.