Community colleges serve an important role in local communities across the United States. These institutions, based on their mission, seek to fulfill a social contract as partner in community development in the 21st century. Their function in local and the wider US community is undeniably important; more than half of the college students enrolled in the United States attend community, technical, and junior colleges (Pew Research Center, 2009). Community college leaders face especially challenging times given the economic, social, political, and technological contexts within which these institutions operate. This chapter brings focus to the various nuances of community college educational leadership with specific focus on technology in this new virtual age.