The present paper deals with the structural analysis and the re-design of a cutting head for an automatic crosscutting machine. The machine is already marketed, and can process rectangular section wooden slats. The principal goal of this work is to develop a new mechanism capable of enhancing the productivity of the machine by around 80%. The work has been carried out by means of both numerical finite element analysis tools and analytical models. In fact, a secondary aim of the research is to define an analytical model which can capture the dynamic behavior of the device: this tool will be helpful to the design engineer in order to save costs associated with the development of future head designs.