This study examines how Chief Student Affairs Officers (CSAO) make sense of their role engaging with fundraising at small, private, liberal arts institutions with endowments below the median endowment size of $140.2 million. Specifically examining how they make sense of engaging with fundraising and how they have gained knowledge or experience in fundraising. Over its history, the field of student affairs has evolved to serve the needs of institutions and students, and, with that evolution new focus areas of the role have emerged, including fundraising. Through the exploration of Organizational Sensemaking, this study highlights avenues for future student affairs preparation, training, and education. Through qualitative inquiry, seeking new knowledge, presidential influence, drawing from prior foundations, driven to serve students, strengthening the institution, and harnessing the value of relationships are outlined as ways CSAOs made sense of engaging with fundraising and gaining knowledge on fundraising. [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.]