This study examines the influence of CEOs’ intellectually stimulating behavior, namely, encouraging followers to bring up new perspectives and innovative approaches at work, on employees’ perceptions of the meaningfulness of their work. Drawing from a collective sensemaking lens, we predicted that such CEO behavior would have a greater impact on experienced meaningfulness of work in contexts in which inputs to attributing meaning are less certain and clear-cut. Specifically, we examined the moderating roles of firm performance and industry dynamism. We surveyed the CEOs and employees from 43 firms in innovation-driven industries. Our results show lower firm performance or rapid and unpredictable changes in the industry are associated with a stronger positive relationship between CEO intellectual stimulation and employee work meaningfulness. We discuss the implications of our findings for organizational leadership practices.