Background: Canada is facing its worst crisis among healthcare workers in recent healthcare history. Anxiety, depression, suicidal ideation, and severe burnout are higher than before the COVID-19 pandemic. University Faculties of Medicine (FoMs) are vital to healthcare systems. Not only are they responsible for training personnel, but clinicians and staff from FoMs often work directly within healthcare systems. FoMs include students, staff, residents, faculty members, residents, researchers, and others, many experiencing higher stress levels due to pandemic tensions. Most FoMs emphasize cognitive and psychomotor learning needs. On the other hand, affective learning needs are not as well addressed within most FoMs. Finding innovative means to ameliorate mental and emotional health status, particularly at this critical juncture, will improve health and wellness, productivity, and retention. This article discusses a pilot program, Wellbeing Convene during COVID-19, in a Canadian FoM, which aimed to (1) provide staff, faculty, residents, and students with a toolkit for greater wellbeing and (2) build a sense of community during isolating times. Results: Participants found the program beneficial in both regards. We recommend that these kinds of programs be permanently available to all members in FoMs, at no cost. Wellness programs alone, however, will not solve the root causes of mental and emotional stress, often based on concerns related to finances, hierarchical workplace structures, and nature of the work itself, among other factors. Conclusion: Addressing the mental and emotional health of people in FoMs is vital to improving productivity and reducing stress of FoMs, healthcare professionals, and, ultimately, patients.