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To build Sounding Board, we develop a system architecture that is capable of accommodating dialog strategies that we designed for socialbot conversations. The architecture consists of a multi-dimensional language understanding module for analyzing user utterances, a hierarchical dialog management framework for dialog context tracking and complex dialog control, and a language generation process that realizes the response plan and makes adjustments for speech synthesis. Additionally, we construct a new knowledge base to power the socialbot by collecting social chat content from a variety of sources. An important contribution of the system is the synergy between the knowledge base and the dialog management, i.e., the use of a graph structure to organize the knowledge base that makes dialog control very efficient in bringing related content to the discussion. Using the data collected from Sounding Board during the competition, we carry out in-depth analyses of socialbot conversations and user ratings which provide valuable insights in evaluation methods for socialbots. We additionally investigate a new approach for system evaluation and diagnosis that allows scoring individual dialog segments in the conversation. Finally, observing that socialbots suffer from the issue of shallow conversations about topics associated with unstructured data, we study the problem of enabling extended socialbot conversations grounded on a document. To bring together machine reading and dialog control techniques, a graph-based document representation is proposed, together with methods for automatically constructing the graph. Using the graph-based representation, dialog control can be carried out by retrieving nodes or moving along edges in the graph. To illustrate the usage, a mixed-initiative dialog strategy is designed for socialbot conversations on news articles.