This study presents initial empirical findings that highlight the contingency of the corporate advantage of reallocating resources on specific organizational factors. Focusing on vertical and horizontal organizational configurations, such as the number of organizational layers and product proliferation, I examine their impact on the relationship between inducements and corporate value. Leveraging a unique dataset from the U.S. Medical and Healthcare Marketplace Guide, this study offers comprehensive insights into the U.S. pharmaceutical industry from 1983 to 1992. My findings support existing research, demonstrating that heightened industry-level volatility enhances firm value through increased option value associated with resource reallocation. Theoretically, I contribute by introducing two novel boundary conditions, showing that the positive relationship between industry-level volatility and firm value diminishes as the number of organizational layers increases. I argue that having more intermediate layers reduces top-level oversight, increasing the likelihood of resource misallocation. A higher number of intermediate layers can delay reallocating resources, hindering timely exits from underperforming businesses. Additionally, when multi-business firms pursue an across-niche product proliferation strategy, the positive relationship between industry-level volatility and firm value diminishes due to increased coordination demands and potential cognitive biases.