This article examines the salary trajectory of teachers as they move up the career ladder into leadership positions. The issue of compensation is set in the context of a principal shortage that has been widely reported and discussed in the literature. Urban schools are shown to experience the principal shortage differently from rural schools. District size and school type show significant differences in the additional compensation offered for moving from teaching to various leadership positions. The influence of salary is discussed in concert with the changing role of the principalship and candidate's concerns about increasingly less desirable working conditions for school leaders. (Contains 5 tables.)