This multisource, multilevel study examined the importance of supervisors as work-life-friendly role models for employees’ boundary management. Particularly, we tested whether supervisors’ work-home segmentation behavior represents work-life-friendly role modeling for their employees. Furthermore, we tested whether work-life-friendly role modeling is positively related to employees’ work-home segmentation behavior. Also, we examined whether work-life-friendly role modeling is positively related to employees’ well-being in terms of feeling less exhausted and disengaged. In total, 237 employees and their 75 supervisors participated in our study. Results from hierarchical linear models revealed that supervisors who showed more segmentation behavior to separate work and home were more likely perceived as work-life-friendly role models. Employees with work-life-friendly role models were more likely to segment between work and home, and they felt less exhausted and disengaged. One may conclude that supervisors as work-life-friendly role models are highly important for employees’ work-home segmentation behavior and gatekeepers to implement a work-life-friendly organizational culture.