Growing mental health treatment access disparities elevate the urgency for identifying and implementing innovative approaches for delivering evidence-supported interventions. Work-related cognitive behavioral therapy (WCBT), a technology-assisted CBT (t-CBT) designed to address social anxiety and employment outcomes among job seekers at vocational service centers and for delivery by vocational service professionals, offers a promising way to increase access to needed mental health care. This qualitative study, guided by the Organizational Transformation Model (OTM), explored factors related to WCBT's implementation at two Jewish Vocational Services (JVS) Human Service sites in Detroit, MI and Los Angeles County, CA. Twenty-seven staff-stakeholders across the two JVS sites completed in-depth, semi-structured interviews focused on their experiences with WCBT over the four-year study period. Thematic analysis identified five core codes that most broadly captured participants' perceptions of WCBT implementation and the factors influencing implementation, including: (1) Need, (2) Buy-in and engagement, (3) Communication, (4) Sustainability concerns, and (5) Implementation facilitators. Core codes aligned with OTM factors related to impetus to transform, improvement initiatives, integration across boundaries, alignment from top to bottom, and leadership. Findings identify implementation strategies likely to optimize uptake and sustainability of WCBT within JVS sites that can be tested in a larger, multi-site implementation trial.