We study path-dependence of technological systems and power relations inside companies. While existing literature suggests power relations and technology to be path-dependent and influenced by each other, interactions across these evolutionary processes remain poorly understood. We studied the history of four retail firms over forty years, applying event structure analysis to explicate key dynamics. Companies exhibited two episodes of converging path dependency, where power relations further increased technological inertia. In each case, power initially concentrated outside the central headquarters. Path-breaking change led all firms to centralize power and implement networked IT systems supporting central control. We discuss the ability of converging technological and organizational path dependencies to create competitive disadvantage. Widely available technological advances create advantage even when competitors have similar existing systems, when power structures are strongly path-dependent, impeding technological change. Thus, company owners ought to create path-breaking disruptions in power relations when technological adoption provides value.