Competing favorably in the market requires finding a perfect fit between a firm’s resources and the business environment. Strategy is the stewardship by top management that aligns organizational resources and capabilities to the environment with the ultimate goal of achieving superior and sustainable performance. The current study was designed to determine the influence of competitive environment on the relationship between top management team characteristics and strategy implementation. The study adopted the descriptive cross-sectional survey design. Data was obtained by administering structured questionnaire mailed to top managers in tea factory companies in Kenya. The moderation test was carried out using the product term of the standardized scores for top management team characteristics and competitive environment respectively. Data was processed through regression analysis. While we demonstrate that top management team characteristics had significant influence on strategy implementation, the results of moderation tests were not statistically significant. Consequently, our hypothesized moderating influence of competitive environment on the relationship between top management team characteristics and strategy implementation was not supported. Our findings raise theoretical questions on whether competitive environment is more relevant during strategy formulation process or execution stage. We conclude that companies implementing strategy in stable competitive environment have predictable implementation of planned strategy. We further conclude that external insulation from competition by umbrella marketing agency reduces the influence of factors within the competitive environment on the relationship between top management team characteristics and strategy implementation. However, the temporary insulation of the firm from competition exposes it to competitive disadvantage in the event that the marketing agency is destabilized by forces both from within and external to it.