This study applies a contingency perspective to examine how the intra-organizational context influences the relationship between cross-functional collaboration and product innovativeness. It focuses on the role of (1) formal, structural factors directly controllable by top management decisions and (2) more intangible, relational factors as potential enhancements of the firm's ability to convert cross-functional collaboration into product innovativeness. A study of 232 firms confirms the hypotheses, finding that the relationship between cross-functional collaboration and product innovativeness is stronger for higher levels of decision autonomy and shared responsibility (structural context) and social interaction, trust, and goal congruence (relational context). In addition, a post-hoc analysis using a configurational approach to organizational contingencies reveals that organizations' relational context is more potent than their structural context for converting cross-functional collaboration into product innovativeness. The study's implications and future research directions are discussed.