Higher education is going through a significant period of change following the COVID-19 pandemic. The increased technological capacity and desire for online modalities are both a great opportunity and a potentially challenging burden. Although they serve the most marginalized students, community colleges are often vastly under-resourced, leaving them vulnerable to significant challenges during systemic shifts, like transitioning to remote work or online learning. During the COVID-19 global pandemic, many colleges were forced to implement remote work and develop policies to guide the change. In this study, the perspectives of 10 rural community college presidents are analyzed to identify both the opportunities and challenges facing the workforce as remote work policies are developed and evolve. Presidents shared perspectives on these policies and several guidelines emerged from their collective interviews, including the importance of creating policies that can enhance employee retention and recruitment, balance institutional and staff needs, include provisions for training, and maintain a focus on student success.