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Understanding the practical implications related to experiential learning is complex. It is important to first view experiential learning as an umbrella term under which work-based learning (WBL) is housed. To further particularize, there are different avenues for students to pursue work-based learning opportunities (WBLOs), with internships and cooperative education being two. Although these are not new learning environments, understanding and clearly defining them (to both internal and external bodies) is increasingly necessary. In Kentucky, WBLOs are part of the political discourse on postsecondary education. The Council on Postsecondary Education (CPE) and local economic development agencies have incorporated strengthening and growing WBLOs into their strategic plans. This demand is echoed by students and parents. By interviewing faculty with varying enrollments in their WBLOs, this study set out to explore influences on the development and implementation of these experiences from their perspective. The dissertation is written in three manuscripts, including a companion piece written in collaboration with Robert Boone that examines WBLOs from a complementary faculty (McCrary) and student perspective (Boone). It situates the problem of practice (WBLOs) in the current landscape of Kentucky Community and Technical College System. The second manuscript describes anticipated and unanticipated findings related to the development and implementation of WBLOs drawn from my interviews with WBLO coordinators across the state. Selected examples include the role of the advisory board and faculty background on the development of WBLOs and stakeholder preparation and conveying benefits to the community during implementation. The third manuscript explores obstacles encountered and offers potential avenues to circumvent or overcome said obstacles based on information collected through the interviews of this qualitative, exploratory study. This dissertation will be of use to both senior administrators interested in increasing WBLOs at their institution and to faculty who are interested in offering the opportunities to their students. This study offers insight to current practices related to WBLO development and implementation and offers potential avenues to overcome obstacles.