The advent of charter schools has been one of the biggest reform initiatives in the history of schooling in the US: charters have significantly altered the landscape of many of our country’s largest public-school systems (Bracey, 2002; Hassel, 2009; Hill, 2006). Recent studies have examined a number of aspects of charter school leadership; however, there has been little research on charter school chief executive officers (CEO). The CEO is a relatively new role that oversees the entire charter school or network and is almost always independent of the principal. This mixed-methods study examined the organizational dynamics of Philadelphia Charter School CEOs by using a survey, personal interviews, and quantitative data analysis to obtain information regarding all CEOs of Philadelphia. Interviews were focused on the CEO job role and day-to-day duties, CEO successes and struggles, and what prior experiences prepared CEOs for this role. The quantitative findings show two correlations: suggesting that male CEOs and CEOs of stand-alone schools are in charge of schools with higher school performance. Five common themes emerged across CEOs during interviews: loneliness, overconfidence, under preparedness, non-traditional career path, and having a prior work experience in the field of education was crucial to success. Lastly, it was discovered that certifications and prior education experience were not commonplace for current CEOs, 19 of the 64 CEOs in this study did not have prior education experience. / Educational Leadership