Recent developments in novel engineered mass timber products and connection systems have created the possibility to design and construct tall timber-based buildings. This research presents the experiments conducted on the steel-wood connection as main energy dissipating part of a novel steel–timber hybrid system labelled Finding the Forest Through the Trees (FFTT). The performance was investigated using quasi-static monotonic and reversed cyclic tests. The influence of different steel beam profiles (wide flange I-sections and hollow rectangular sections), and the embedment approaches (partial and full embedment) was investigated. The test results demonstrated that appropriate connection layouts can lead to the desired failure mechanism while avoiding excessive crushing of the mass timber panels. The research can serve as a precursos for developing design guidelines for the FFTT systems as an option for tall wood-hybrid building systems in seismic regions.