With structural changes in work arrangements, employee retention becomes more important for organizational success. Guided by the Ability, Motivation, Opportunity (AMO) framework, this study investigated the factors affecting remote workers’ job satisfaction and personal wellbeing in Utah. From a sample of n = 143 remote workers, the study used a correlational design to identify the significant predictors of job satisfaction and personal wellbeing. It mapped the relationships between significant predictors of job satisfaction and personal wellbeing and explored the role of human resources (HR) policies and organizational culture in a remote work environment. Results showed intrinsic motivation, affective commitment, opportunity, and amotivation affected employee job satisfaction, while self-efficacy, amotivation, and job satisfaction affected personal wellbeing. A structural equation model (SEM) showed that remote workers with higher levels of self-efficacy, lower amotivation, and higher job satisfaction were likely to have greater personal wellbeing compared to others. When exploring the role of HR, findings showed that HR bundles and organizational culture indirectly affected job satisfaction but had a direct effect on the most important predictors of job satisfaction and personal wellbeing. Overall, results demonstrated the interconnectivity of HR practices, AMO factors, job satisfaction, and personal wellbeing.