This dissertation is comprised of two essays that broadly consider the role human capital plays in the matching process between individuals and institutions and builds on prior education literature that has found growing evidence that economic choices and opportunities are inextricably linked to human capital investment. The essays in this dissertation also build on the labor-economic tradition of bringing to bear new data sources that involve both collecting new data and combining these data with previously existing data sources in new ways so as to permit the study of interesting issues that could not have been addressed in the absence of these data. Using recent institutional data from the oldest stand-alone honors college in the country, Chapter II of this dissertation studies how the application and enrollment decisions of honors college students differ from the general population of students considering a large public university. Overall, the results suggest that honors college applicants and enrollees are drawn from the right-tail of its host institution's ability distribution, independent of residency status. Nonetheless, honors college applicants are still more likely to enroll in selective and liberal arts institutions than the general pool of admits to a large public university, which is only partially offset by the effect of honors college admission. Chapter III exploits the attributes of the higher education industry to examine the role of training and ability in the placement of university presidents within the hierarchy of U.S. institutions. The empirical analysis uses two data sets, the American College President Survey conducted by the American Council on Education and a digitized sample of 2009 curriculum vitae for presidents at 212 top U.S. universities, to model the factors that determine who among the pool of university presidents place at Carnegie-classified research institutions. The findings suggest that the rise to the presidency of a research institution depends on the investments in research-specific human capital over the entire course of a career, which is consistent with prior evidence that the knowledge of the research enterprise is critical to the success of such institutions. This dissertation includes both previously published and unpublished, co-authored materials. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://www.proquest.com/en-US/products/dissertations/individuals.shtml.]