This dissertation explores telework in the Chilean public sector, highlighting the tension between demands for organizational flexibility and a centralized, compliance-driven bureaucracy. While promoted as a form of modernization, telework requires fundamental changes in work coordination, monitoring, and evaluation, challenging traditional systems based on physical presence and hierarchical control. This study develops a multi-level framework to explain telework variation, linking (1) institutional pressures, (2) organizational pathways, and (3) managerial experiences. It uses institutional theory to show how regulative, normative, and cultural forces influence the design and legitimacy of telework programs, and JD-R theory to examine how these conditions affect managers' experiences and attitudes. The study uses a mixed-methods approach. It first uses case studies to compare two Chilean public agencies. Then, a survey of 594 public managers across 15 agencies assesses perceptions of telework and tests the effects of job demands and resources with structural equation modeling. Findings show telework is shaped by distinct pathways. Entrepreneurial implementation relies on relationships, experimentation, and local legitimacy, while isomorphic adoption emphasizes compliance, risk management, and standards. Despite similar adoption levels, these pathways create different dynamics and constraints. Telework brings new demands for managers, such as coordination, monitoring, and fairness, while organizational support reduces strain and boosts job satisfaction and commitment. The dissertation advances public administration by viewing telework as an implementation process shaped by institutional context and by integrating institutional and JD-R theories to link macro structures with micro outcomes. Findings highlight the need to align flexibility reforms with systems that enable managerial discretion, as misalignment may increase managerial burden.