If the most precious product developed in education is the student, then our most prized commodity should be the classroom teacher. According to numerous studies (Allen, Pianta, Gregory, Mikami, & Lun, 2011; Clotfelter, Ladd, & Vigdor, 2010; Darling-Hammond, 2000), the greatest influence on a student's achievement is the classroom teacher. School leadership takes seriously the issues of teacher satisfaction and retention in order to benefit from the growth and experience of a strong teacher. The quest is to discover ways to influence teachers to remain in the profession in order to grow into great classroom teachers. In "Good to Great," Jim Collins (2001) describes the highest level of leadership as a Level 5 leader, who is a servant leader. Collins contends the companies that evolved from good to great had Level 5 leaders. The transformational power of the servant leader and the effect that he/she has on a group of employees and colleagues to lift an organization from mediocrity to greatness is astounding. The practice of servant leadership in schools could have a similar impact, particularly as it relates to teacher satisfaction and retention. Little quantitative research has been conducted on the influence of the servant leader. This quantitative study sought to examine the relationship between perceived servant leadership characteristics of the high school principal and teacher retention and job satisfaction. The purpose of this study was to determine whether teachers who perceive their principals to exhibit servant leader characteristics have increased job satisfaction and desire to remain in that school with that principal.