With tightening university budgets, never before has the activity level of research grant proposal writing been more intense. With increased proposal numbers, including for the National Science Foundation's (NSF) prestigious CAREER award, has also come increased competition and decreased funding rates. This dissertation has searched for successful and unsuccessful characteristics from funded and unfunded CAREER proposals. The research focused on a study of two key subjects: 1) a corpus of 20 texts that included 12 funded proposals and 8 unfunded proposals from across NSF programs, and 2) an ethnographic analysis comprised from interviews with 14 NSF program officers (PO) from varying programs. Coding elements with the texts to uncover topical chains of content, rhetorical, and document design strategies revealed sound rhetorical moves and rhetorical mistakes. The study also illustrated evidence of adherence to or neglect of NSF-mandated writing/formatting conventions as connected to the likelihood of receiving funding. Moreover, the study revealed conventions that have developed for the genre that are not prescribed by NSF but that, nevertheless, seem to be expected. Through genre field analysis, the study's interviews with program officers (PO) revealed a system of genre-agents and player-agents that interact together in a highly rhetorical and social system. This system, comprised of locales in which a multitude of play scenarios can be enacted to exert influence, operates within fairly exact rules of play. Such rules may be published by NSF or simply be "understood," yet principal investigators (PI) are held accountable for them regardless. The ethnography created from interviews with POs revealed multiple genre field elements (e.g., genre- and player-agents, transformative locales, play scenarios, penalty conditions) as well as common mistakes and best practices. A complete mapping of the CAREER award proposal preparation, submission, and review process resulted from the study, which mapping has offered insightful strategies to expand PI (and other agents') influence on the funding process. The dissertation concluded by offering investigators a step-by-step process to identify and map the elements of the proposal genre field in which they operate.