The purpose of this study was to conduct a gap analysis to examine the knowledge, motivation, and organizational influences that interfere with establishing educational and work-based learning opportunities for youth development professionals. This project employed a mixed-method data collection and analysis approach. These professionals' current understanding of their role and the current educational and learning opportunities available to them were assessed through surveys and interviews. Survey results revealed that a high percentage of respondents expressed satisfaction in their roles and dissatisfaction in their career prospects within the organization. Youth workers also confirm they receive limited in-person and online training but find coaching and supervision from their managers beneficial. A high percentage also indicated they have fewer than two hours of weekly planning time. Interviews were used to triangulate survey results. While there are several learning experiences available, local youth development professionals are not accessing them readily. Interviews provided insight into the competencies essential to the role and the variety of resources available to front-line staff members. Participants provided recommendations for tangible approaches to expanding the career trajectory of youth workers and advocated for systemic solutions to address the barriers to advanced work-based learning. The implications of this study have a direct impact on the administrative and programmatic constructs of the out of school time sector. This study culminates with an explanation of context-based solutions grounded in the literature, study results, and the New World Kirkpatrick Model, in addition to an evaluation and implementation plan and recommendations for future research.