Beginning with Harvard in 1636, liberal arts colleges have a storied place in United States higher education history. Given that the institutions are faculty-led, it is perhaps not surprising that the vast majority of liberal arts college presidents have traditionally come from the ranks of faculty. Yet the context—as defined by institutional characteristics such as geography, religious affiliation, graduation rates, selectivity, or size—facing today’s 248 stand-alone liberal arts colleges varies dramatically from one institution to another. Overall, liberal arts colleges as a group are challenged, as well as many, but not all, of the individual institutions. The contextual perceptions and experiences of the liberal arts college presidents involved in this research are somewhat more nuanced but point to a rapidly evolving industry. Although search firm executives now conduct the vast majority of presidential searches, this research shows that they do not agree on a uniform definition of a nontraditional president. Quantification of the number of nontraditional liberal arts college presidents shows that they are on the rise across the board and moving into the mainstream, albeit from a variety of pathways. However, a substantially higher percentage of traditional presidents are women versus nontraditional presidents. Further, institutional context is a factor that influences the likelihood of having a nontraditional president. Institutional characteristics that indicate an increased prevalence of nontraditional presidents include lower wealth, lower ranking, and religious affiliation, among others. Search firms play an increasingly important role in presidential searches, and their executives see a number of important trends underpinning the rise of the nontraditional president. Despite the increase in numbers of nontraditional presidents, search firm executive interviews in the research clarify that the presidency is becoming an increasingly difficult role and that the nontraditional pathway is still fraught with difficulties. Nevertheless, search executives outline successful strategies that nontraditional candidates can pursue to increase their chances of selection. Nontraditional presidents not only share their lessons learned on being selected but also provide different lenses for candidates to consider fit and to make a successful transition to liberal arts college president.