The construction sector is investigating wood as a highly sustainable material for fabrication of architectural elements. Several researchers in the field of construction are currently designing novel timber structures as well as novel solutions for fabricating such structures, i.e. robot technologies which allow for automation of a domain dominated by skilled craftsman. In this paper, we present a framework for closing the loop between the design and robotic assembly of timber structures. On one hand, we illustrate an extended automation process that incorporates learning by demonstration to learn and execute a complex assembly of an interlocking wooden joint. On the other hand, we describe a design case study that builds upon the specificity of this process, to achieve new designs of construction elements, which were previously only possible to be assembled by skilled craftsmen. The paper provides an overview of a process with different levels of focus, from the integration of a digital twin to timber joint design and the robotic assembly execution, to the development of a flexible robotic setup and novel assembly procedures for dealing with the complexity of the designed timber joints. We discuss synergistic results on both robotic and construction design innovation, with an outlook on future developments.