Purpose: Effective school operations rely on distributed leadership that enables timely innovation and the resolution of challenges hindering school development. Although distributed leadership involves both principals and teachers, little research has simultaneously examined their perspectives on how distributed leadership, innovativeness, and contextual barriers interact to influence student achievement. This study investigates how distributed leadership relates to student achievement through school and team innovativeness, emphasizing comparisons between principals’ and teachers’ viewpoints. Methodology: Using the linkage data of TALIS 2018 and PISA 2018, we conduct a school-level regression model and a multilevel regression model to analyze the pathways from distributed leadership to student achievement, incorporating school innovativeness, teacher team innovativeness, and hindering conditions of school development. Finding: Distributed leadership is associated with innovation at both school and teacher team levels. Perceptions of how innovativeness impacts student achievement differ among principals and teachers. Teachers’ assessments of team innovativeness are positively related to student achievement, partly due to varying developmental conditions across schools. Implications: The findings indicate that perceptions of innovation between principals and teachers may stem from a dynamic and uneven process. A shared understanding of their ecological niche helps support consistent school practices as distributed leadership becomes evident. Organizational innovation and addressing challenges that impede school development could be crucial pathways through which distributed leadership affects student achievement.