Higher education and workforce systems have reformed over the last decade. These reforms are in response to an evolving economy, irregular political environment, a damaging pandemic, and declining enrollment in postsecondary education, and are an attempt to better prepare employees for new occupations and increased competition for students. One subsequent innovation was the convergence between employers and HEIs to reshape traditional continuing education opportunities through partnership models. Leaders of HEIs and employers were incentivized to pursue new relationships to support entry-level workers' access a bachelor's degree (Crow & Dabars, 2020; Holzer, 2015; Schwartz, 2016). These new access points to education benefited both higher education systems and workforce progress. Although academic partnerships using education benefits as a base were common, this cross-sector partnership development has been an understudied strategy for expanding, attracting, and educating the workforce. In this model, it was used to improve higher education enrollment, persistence, upskilling of employees, and upward mobility. Investigating the emergence of these relationships informs related scholarship, policy, management practices, and frameworks. The approach to this study offered an in-depth exploration, interpreted through a mutual, cross-sector lens, to the development of partnerships that funded access to a bachelor's degree education. Data were collected through semistructured interviews with senior managers and executives involved in partnership development and stewardship from higher education, industry, and intermediaries. Findings organized into three categories including (a) initiation (b) integration, and (c) signals of success. A spectrum of engagement centered around the values and needs of likeminded leadership and organizational culture, investment in an infrastructure, a strategic approach to workforce training, alignment, trust, communication, and an appreciation of organizational goals leading to collaborative decision making. Guided by grounded theory and qualitative research, the study illustrated the convergence, complexities, and challenges to integrate two organizations from different sectors. Further, insights identified factors that work for and against partnership success. The results yielded a rich insider perspective on various facets of the partnership's origination, evolution, operation, and continued advancement. Findings also provided suggestions for future research as well as recommendations for practice, such as design principles, levels of engagement, and details of the evolving landscape. [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.]