Embodiments described herein provide a system for facilitating dynamic content distribution in an enterprise environment. During operation, the system determines a set of logical groups based on a set of grouping criteria. A respective logical group can include one or more devices managed by a controller and a network that provides connections among the one or more devices. The system categorizes the set of logical groups based on exogenous information associated with a respective logical group and determines a corresponding condition of measurement for a respective category of links in the enterprise environment. The system then schedules a link for measurement based on the condition of measurement and the categorization of the set of logical groups.