The rise of telework during the COVID-19 pandemic has fueled intense debate over whether it boosts or hinders employee performance. This study investigates the complexities of telework’s effects, emphasizing that its outcomes are not one-size-fits-all. Specifically, we explore how telework influences engagement and self-rated performance, moderated by organizational roles (managers vs. non-managers) and job tenure. Using the Job Demands-Resources (JD-R) model and longitudinal data from 278 white-collar professionals, we show that non-managers benefit from telework, reporting higher engagement and self-rated performance. Conversely, managers experience declines in engagement and self-rated performance when confronted with the demands of remote challenges. Our results also indicate that telework has little impact on engagement levels for employees with longer tenure, regardless of their role. These findings challenge the idea that telework has universally positive or negative employee effects, underscoring the importance of context in understanding its impact. As organizations move toward hybrid work models, this research offers critical insights for tailoring telework strategies to meet the diverse needs of employees based on their roles and experience.