The next generation of leaders in medicine brings unique perspectives and skill sets to the healthcare milieu. It has been suggested that trainees, and their skillsets, are better engaged when medical hierarchical structures are softened. Here, we explore that hypothesis in the context of trainee leadership within medical advocacy efforts. We report objective social media measures along with anecdotal lessons from teams in which trainee leadership was employed. Specifically, we use two 'case studies' in which trainees' skills facilitated the growth of public health and gender equity advocacy efforts on social media. We report on the success of these initiatives on two fronts: first, in reaching the target audiences of these platforms; second, in retaining trainee leadership for, and flattened hierarchical structuring of, teams.