This study examined how Chief Information Officers (CIOs), also known as Information Technology leaders, understand the use of technology as a strategy for reducing academic costs in small, private, liberal arts colleges in New England. Semi-structured interviews were conducted with eight CIOs throughout small, private, liberal arts colleges in New England. Transcripts were analyzed using Interpretative Phenomenological Analysis (IPA) to identify themes. Four major themes emerged: the importance of positioning Information Technology (IT) within the college, the use of available data, the offering of alternative education models, and the opportunities around consortiums and institutional partnerships. These findings were considered in light of the extant literature and Snowden and Boone's Cynefin framework and suggest opportunities for: assessing the position of IT in an organization and how that supports strategy; building out a data strategy on a campus that prioritizes considerations of what to assess and measure; thinking through alternative delivery, such as online learning; and considering consortium and institutional partnerships. [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.]