The 21st century business environment is challenged with a scarcity of skilled professionals and the shortage is forecasted to increase over the next 5 years. The United States defense acquisition community recognized personnel deficiencies and plans to hire approximately 20,000 acquisition professionals by 2015. To help address the defense acquisition workforce challenges, several leadership development programs have been instituted to accelerate a pipeline of technically skilled and leadership capable contracting professionals. The purpose of the qualitative single descriptive case study was to explore the progress of National Contract Management Association (NCMA)-Contract Management Leadership Development Program graduates in acquiring management positions to understand the impact the program had on closing leadership gaps in the contract management field. Data analysis performed on participant interviews highlighted that the majority of participants did not start with a career plan or initiate much of one during the program, however, some participants had a sense of career direction. Following graduation, participants started to appreciate the value of sharing career plans with mentors and leaders. During the program some students expressed frustration on being able to apply program curriculum to their current career state. Program graduates believed that the NCMA could increase marketing and advertisement efforts to capture more employer involvement. The case study revealed that 92% of sample participants experienced career changes, with two participants reaching executive level positions in the contract management profession. [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://bibliotheek.ehb.be:2222/en-US/products/dissertations/individuals.shtml.]