Small- and medium-sized enterprises (SMEs) can have significant resources, capacities, and influence in their communities, suggesting they have the potential to be agents for transformative sustainability. However, SMEs will need to move beyond firm-centered sustainable business practices towards strategic approaches that encompass and contribute to resilience-building processes. Amid the unfolding COVID-19 pandemic, we explored what types of sustainable business practices of SMEs can contribute to individual, organizational, and community resilience. We identified six clusters of practice that are important in this regard. The clusters are not solely technical or “environmental” but rather illustrative of deeper sustainable values shaped by organizational structure, culture, and behavior. This paper suggests that SMEs can pursue transformative approaches to sustainability that are more environmentally, socially, and economically sustainable and better able to withstand shocks like the COVID-19 pandemic and can be significant contributors to community resilience. We conclude with a series of future research priorities critical to examine a largely unexplored nexus in the private sector, the linkages and dynamics between sustainability practice, resilience building, and broader community pathways.