This thesis empirically explored the impacts of IT investment on three different scenarios under the common denominator / threads of IT investments. It comprises three different essays on the impacts of IT investments. IT investments and its impact on many aspects of the firms are well known - like performance / productivity, output, market value etc. But I looked into areas that were not explored before and examined events that didn’t take place after the advent and integration of Information Technology – like the past financial crisis. The main contribution of my dissertation is to examine how IT investments helps in the debt market, how it helps firms fare comparatively better during crisis period and how CEO characteristics influence the well-established existing link between IT investment and Innovation intensity. The first essay examines the effect of IT investment on the cost of bank loan for firms. We argue that IT affects the decision of banks through three mechanisms: wealth effect, risk effect, and information effect. First, IT investment serves as a signal for higher future revenue and lower operational costs, thus greater future cash flows. Second, on one hand, IT may be able to reduce the risk of being locked out to competition or adverse situations; on the other hand, IT investment itself can bring risk to business. Last, the use of IT can lead to better information quality and thus reduce the information asymmetry between firms and banks. Using a sample of 270 firms between the year of 1991 and 2006, we find that IT investment is associated with lower interest rate from banks. More important, we find the strength of this relationship is contingent upon the role of IT in the industry and time period. In my second essay, the goal was to investigate whether IT investment contributed to better or worse performance during the financial crisis of 2007-2009. We took the available data for U.S. public companies (the final sample comprises 570 companies) and traced IT investments made in the years prior to the crisis period, we checked the impact of IT investments on the annual stock returns and relative changes in return (as well as for book values). After controlling for relevant risk and other independent variables during the 2007-2009 periods, we found evidence that indicates that although most of the firms suffered during the crisis period, expenditure in IT was significantly associated with relatively better performance for sample firms during the crisis period. The third essay brings in the role of CEO to examine whether CEO’s characteristics affects the already established link between IT investments and Innovation activities. We constructed data from multiple sources; we also developed empirical model to test our hypothesis and ran a series of regression tests. We find that CEO’s managerial ability and risk-taking incentive (determined by compensation scheme) are complements for IT investment. Thus for CEOs with lower ability and/or lower risk-taking incentive, firms can still achieve higher innovation efficiency by increasing expenditure in IT. On the other hand, CEO’s ownership of the firm substitutes the link. CEO with larger ownership enhances firm’s innovation efficiency by due diligence, but not necessarily through the channel of IT investment. In together, this paper shows that CEO is an important and significant factor in the conversion of IT investment to innovation efficiency.