At the intersection of communication studies, information science, user experience (UX), and education, one way to reduce digital inequalities and provide better opportunities for decent work is AI-driven learning experience platforms (LXP) and learning management systems (LMS). This chapter explores the use of AI-driven LXPs and LMSs for professional development purposes of communication and media professionals to reduce digital inequality in the urban regions of Puerto Rico. This research employs semi-structured user interviews and integrated case studies alongside activity theory, diffusion of innovations, and digital divide theory to critically examine digital learning platforms. The primary goal of this study is to provide design and policy recommendations for LXPs and LMSs so they may better serve the development needs of communication and media professionals in Puerto Rico.