Virtual schools are one of the fastest growing educational options for students in the United States. In spite of the increase in virtual program options and enrollment, limited research has been conducted on how virtual school principals lead their organizations. This qualitative case study explores the challenges facing virtual school principals and how these leaders navigate these challenges. Data were collected through semi-structured, one-on-one interviews with 20 public, private, and charter virtual school principals from across California. The findings from this study identified the essential skills and ways in which virtual principals overcome leadership challenges. These factors included: Being open to new ideas, taking positive risks, staying flexible, empowering staff, communicating effectively, and serving stakeholders. The findings from this study can offer insight to many traditional brick and mortar school leadership that are holding fully online classes due to COVID-19.