The purpose of this study was to examine the relationship between teachers’ perceptions of career readiness as an outcome of secondary schools and their intentions to teach employability skills in their classrooms. Additionally, the study sought to explore the impact of selected teacher demographics on teachers’ perceptions of career readiness. The target population was secondary school teachers in North Dakota. Total study participants included 1,209 (N) teachers from a census sample of North Dakota teachers. Respondents completed a questionnaire which included two instruments intended to assess teachers’ perceptions of career readiness and their instructional intentions related to employability skills, as well as selected demographic questions. From the findings of the study, it can be concluded that there is an association between teachers’ demographic characteristics and their perceptions of career readiness. Specifically, teachers who taught Career and Technical Education (CTE) and special education courses placed a higher level of importance on the development of career readiness than teachers who taught core academic and elective/other courses. Additionally, perceptions of career readiness were significantly more positive among teachers who had willingly engaged in more professional development related to the instruction of employability skills compared to those teachers who attended fewer workshops or who were required to attend workshops. Teachers who worked in school districts that required the assessment of employability skills had significantly more positive perceptions of career readiness than teachers who taught in schools that required fewer or no skills to be assessed. According to the findings, teachers’ intentions to teach employability skills can be predicted by their perceptions of career readiness. Consequently, increasing teachers’ positive perceptions of career readiness should increase their intentions to teach employability skills in their classrooms, thus fostering the development of career readiness among their students. Based upon the evidence collected through this study, school leaders and policy makers may be able to positively impact teachers’ perceptions of career readiness through engagement in meaningful professional development, implementation of effective policies regarding the assessment of employability skills, and utilization of consistent and clear communication regarding the purpose of career readiness development and its connection to employability skills.