Enterprises operate in dynamically changing environments, consequently, information systems (IS) are a subject to continuous changes. The IS need to be adjusted to different customers, markets and run-time contexts affecting their design and delivery. Variability and customization of the information systems has become a serious challenge. Capability Driven Development (CDD) has been proposed as a new approach for dealing with variability. CDD allows delivering enterprise capability in dynamically changing circumstances - contexts. To model enterprise capabilities, concepts defined in the Capability meta-model are used. This paper discusses initial Capability modeling experiences. The main emphasis is put on the Capability design phase of the CDD approach. Several empirical cases are included to share the Capability modeling experiences, to validate the Capability meta-model as well as to discuss the difficulties of Capability modeling, open issues and future work