As 80-85% of all corporate information remains unstructured, outside of the processing scope of enterprise systems, many enterprises rely on Information Systems that cause them to risk transactions that are based on lack of information (errors of omission) or misleading information (errors of commission). To address this concern, the fundamental business concept of monetary transactions is extended to include qualitative business concepts. A Transaction Concept (TC) is accordingly identified that provides a structure for these unstructured but vital aspects of business transactions. Based on REA (Resources, Events, Agents) and modelled using Conceptual Graphs (CGs) and Formal Concept Analysis (FCA), the TC provides businesses with a more balanced view of the transactions they engage in and a means of discovering new transactions that they might have otherwise missed. A simple example is provided that illustrates this integration and reveals a key missing element. This example is supported by reference to a wide range of case studies and application areas that demonstrate the added value of the TC. The TC is then advanced into a Transaction-Oriented Architecture (TOA). The TOA provides the framework by which an enterprise’s business processes are orchestrated according to the TC. TOA thus brings Service-Oriented Architecture (SOA) and the productivity of enterprise applications to the height of the real, transactional world that enterprises actually operate in.