This paper presents new evidence challenging traditional views on specialization. Analyzing data from GitHub, covering 35 million task allocations across 64,400 software development teams over seven years, I find a negative link between organizational specialization and key productivity metrics, such as output quality, quantity, and user issue resolution time. To demonstrate causality, I leverage the introduction of an automatic task assignment feature on GitHub that evenly distributes tasks among certain team members. After adopting this feature, teams show reduced specialization and improvements in output quality and quantity,along with an increase in team communication. These results highlight a trade-off in non-routine production: while specialization increase task-specific skills, it hinders vital cross-task knowledge transfer essential for innovation.