(1) Background: Secure employment has been recognized as a social determinant of health for people living with HIV (PLHIV), but limited research has been conducted to understand the employment needs and vocational decision-making process of those who are employed. The purpose of this study is to examine the applicability of the client-focused considering-work model to assess the employment outcomes and employment decision-making phases of a sample of employed PLHIV. (2) Methods: This study analyzed data of 244 employed PLHIV who completed National Working Positive Coalition’s Employment Needs Survey which included a 20-item Considering Work Scale- Employed version (CWS-Employed) and a single-item Classification of Employment Status Scale (CESS). Factor analysis was used to evaluate the CWS-Employed. Chi-square tests of homogeneity of proportions were conducted to assess the domain-specific needs of individuals in each phase of employment decision-making. (3) Results: Our findings revealed high rates of insecure employment and diverse vocational service needs among research participants. Additionally, the CWS-Employed accurately predicted 71% of the self-reported classification of phases of employment decision-making. (4) Conclusions: When investigating the role of employment as a social determinant of health, more research is needed to better understand the vocational needs and outcomes of PLHIV who are working. Improving the measurement of the phases of employment decision-making is needed to better identify appropriate vocational interventions that can lead to improved employment and related health outcomes for this population.