We discuss the possibility of generating spin squeezed states by means of driven superradiance, analytically affirming and broadening the finding in [Phys. Rev. Lett. 110, 080502 (2013)]. In an earlier paper [Phys. Rev. Lett. 112, 140402 (2014)] the authors determined that spontaneous purely-dissipative Dicke model superradiance failed to generate any entanglement over the course of the systems time evolution. In this article we show that by adding a driving field, however, the Dicke model system can be tuned to evolve toward an entangled steady state. We discuss how to optimize the driving frequency to maximize the entanglement. We show that the resulting entanglement is fairly strong, in that it leads to spin squeezing.