The purpose of this study was to determine if superintendent longevity significantly impacted teachers' perceptions of their working conditions. In addition, the study sought to determine if there were differences in perceptions among teachers whose superintendent was beginning (1 or fewer years in current position), emerging (between 2 to 6 years in current position), or established (7 or more years in current position). The study used Callahan and Kowalski's (see Kowalski & Brunner, 2005) five role conceptualizations to chronicle the evolution of the superintendency and to support their argument that the role of the 21st century superintendent has become quite complex and impacts all aspects of a school district, including those areas that have traditionally been relegated to principals. This causal-comparative study used of the results from the 2010 North Carolina Teacher Working Conditions Survey (NCTWCS). Those data were used to determine teachers' perceptions of their working conditions within the state's 115 public, non-charter school districts. In addition, the researcher acquired tenure data for each of the corresponding superintendents who oversaw the 115 districts included in their study. Each school-based, licensed public school employee (e.g., teachers, counselors, media specialists, etc.) in the state (N=119,000) was given the opportunity to take part in the NCTWCS every two years. From that group, 89% percent of those educators (n=105,688) responded to the 2010 survey. Ordinary least squares regression was used to determine if superintendents' length of tenure significantly impacted teachers' perceptions of their working conditions as measured by the survey's responses. A one-way ANOVA was used to test for construct differences among three distinct categories of superintendent tenure. The study revealed that only one of the nine teacher working condition scales, professional development, was significantly related to superintendent tenure (r = -.23, p = .014). There was no statistical significance among tenure groups, indicating that educators did not perceive their working conditions much differently regardless of whether their superintendent was a beginning, emerging, or established leader.