The current study draws on the upper echelons theory to examine the nature of the relationship between top management team (TMT) tenure and a firm's level of entrepreneurial orientation (EO). We find evidence of an inverted-U relationship between TMT tenure and EO using data from firms across three industries with varied industry dynamics. We further introduce a contingency element by demonstrating that TMT industry background heterogeneity moderates the relationship between TMT tenure and EO, where the inverted U-shaped relationship will be more pronounced when the heterogeneity is low and will flatten when the heterogeneity is high. The findings demonstrate the complexity CEOs and governing bodies face while shaping a diverse TMT that can affect EO.