This paper addresses the relationship between knowledge management initiatives in Indian IT organizations and their innovativeness at the organization level by using the survey research methodology. Knowledge management initiatives were measured in the context of cultural, structural, and technological interventions. Innovation was measured in terms of organizational behaviour related to sensitivity, learning, newness, trialability, communicability, risk-readiness, and absorption. A conceptual model was developed to assess the relationship between knowledge management initiatives and innovativeness. A hypothesis that knowledge management initiatives (KMI) influence the innovativeness of the organization was propounded. The questionnaire developed to assess knowledge management initiatives had 60 items, while an already available questionnaire consisting of 65 items was used to measure innovativeness. Eventually, the number of items in the knowledge management initiatives and innovativeness questionnaires was bought down to 45 and 34 respectively. Items were measured on a fivepoint Likert type rating scale, ranging from strongly agree to strongly disagree. The reliability of the questionnaires was checked using Cronbach Alpha. The study was carried out on 84 professionals from 20 Bangalore-based IT organizations that had implemented knowledge management initiatives and had SEI CMM level 5. Means and standard deviations of the variables were computed. The variables were subjected to correlation analysis and factor analysis. A multiple regression analysis was done to identify the influence of knowledge management initiatives on organizational innovativeness. An organizational innovativeness score, was used as the dependent variable and the variables of knowledge management initiatives were used as the independent variables. The results of data analysis showed that the initiatives taken by companies to enhance their knowledge assets fall into the culture, structure, and technology subsystems and that all the three are highly correlated: Technology and culture are more strongly associated with each other, as compared to their association with structure. All the three KMI variables strongly influence organizational innovativeness, with ‘culture’ being the most important. ‘Learning climate,’ a variable of culture, is found to be the most significant of the variables to influence innovativeness. Hence, organizations that lay emphasis on learning and provide excellent training facilities can foster a more innovative environment. Interestingly, ‘risk readiness‘ is not a factor contributing to innovativeness and is not significantly associated with the other variables. The variables like leadership, networking, reward and recognition, structure and technology do not significantly influence innovativeness.