This article presents a societal level cross-cultural analysis that explores the relationship between division of labor and stratification, as well as the effect that information systems and transportation have on this relationship. It is reasoned that social stratification and political hierarchy, as integrative forces are, in part, a function of the division of labor, information systems and transportation. The analysis finds a positive relationship between occupational specialization and political and economic inequalities in 186 small-scale societies, as well as an increased centralization of political and economic power as the cost of exchanging information and resources decrease resulting from innovation in information systems and transportation. In other words, concordant with the conflict view of technology, information systems and transportation innovations seem to have historically benefited mostly the individuals at the top of these political and economic stratification systems as they have an amplifying effect on the division of labor and stratification relationship. The results are discussed in terms of understanding the role that information systems, and transportation play in the de-centralizing or centralizing of resource as well as the decision-making. The article closes with a discussion of possible implications for contemporary societies.