Many workforce-related shortages in the marine transportation industry can be attributed to low birth rates, high levels of upcoming retirements, and evolving occupational complexities of the industry. These challenges may soon place the marine transportation industry in a workforce crisis within some high-demand occupations. This explanatory case study examines how the Marine Institute of Memorial University of Newfoundland’s learns and adapts its practices to more effectively attract, recruit, and retain students for a career at sea. The study applies organizational learning theory as a practical lens to better understand the phenomenon of learning at the organizational level, how it occurs, and the processes involved which enable transformation. The study looks at communicative and collaborative processes of members, including collective thinking, reflection on past experiences, and dialogue, which combined, enable changing conventional ways of thinking. The findings describe how the organization constructs solutions, how it learns and reacts to workforce complexities.