A portable work light is disclosed having a light fixture with one or more rotational degrees of freedom that are automatically actuated such that a light thereof can maintain optimal lighting for a target person in a jobsite environment. Particularly, the portable work light is advantageously configured to track a target person's location within the jobsite environment and automatically reorient the light fixture as needed to maintain optimal illumination of the jobsite for the target person. In this way, the non-value-added work of repositioning or reorienting the work light is eliminated, thus enhancing the productivity of the target person at the jobsite.