Performance impacts of investments in information technologies (ITs) are difficult to evaluate. External investors are further constrained by their lack of visibility into the firm’s intangible, complementary actions and capabilities, creating an information asymmetry between them and the firm’s executives. Building on signaling theory and the research on senior executives’ trades in a firm’s stock, this paper addresses the following question: How are the stock trades by a firm’s senior executives before a major IT investment by the firm associated with the future value to the firm from that IT investment? The results based on data on 2,898 publicly announced IT investments from 926 firms during 2002–2016 suggest that (1) the purchasing of a firm’s stock by its senior executives before a firm’s IT investment is associated with the investment’s longterm effect on firm value; (2) such stock purchases by a firm’s senior executives are associated with a stronger positive (negative) relationship between the IT’s newness and the long-term abnormal returns to firms emphasizing a revenue enhancement (cost reduction) IT strategy; (3) for firms pursuing a hybrid strategy, purchases by CIOs but not purchases by CEOs or the newness of IT are associated with firm value, and (4) purchases made by CIOs provide greater information about the IT investment’s impact on firm value than purchases made by CEOs. We further improve our predictive model’s accuracy from 75% for a model including the fit between IT newness and IT strategy to 80% and 91% when considering purchases by CEOs or CIOs, respectively, and 92% when considering purchases by both executives.