Contemporary enterprise information systems (IS) need to be sustainable in order to provision long-lasting functionality in the presence of changes in customers’ demand, varying environmental aspects, regulations, and many other factors. A key challenge is the need to adjust according to changes at run-time of the IS because not all of them can be anticipated and elaborates at the design time. Lately, the notion of capability has emerged in IS engineering as an instrument that integrates organizational development with IS development, taking into account changes in the application context of the solution. To this end, a methodology and a development environment have been elaborated with the concept of capability in focus, under the name of Capability Driven Development (CDD). It encompasses three key perspectives of organizational design – Enterprise Modeling, context modeling, and pattern modeling. The objectives of this paper are to present how the key perspectives have been incorporated in the CDD methodology, how the methodology has been supported by the CDD environment, and how the methodology and the environment have been used in practice. The application of the proposed approach is discussed for two business cases – outsourcing of energy management services at SIV AG (Germany), and e-government service portfolio provisioning at Everis (Spain).