We show that bright squeezed vacuum light, combined with a single-shot quadrature measurement of the post-interaction light, enables the ultrafast generation of macroscopic quantum states in matter. Although in the weak-coupling regime multiphoton quantum light leaves the unconditional matter state as a classical mixture due to light--matter entanglement, quadrature-based heralding prepares the matter in a Gaussian-weighted quantum superposition. For an ensemble of resonantly electric-dipole-coupled two-level systems, this heralding dynamics acts as a Gaussian filter with respect to the electric polarization, with brighter squeezed-vacuum light accelerating the preparation of the zero-eigenvalue Dicke state. Counter-rotating terms further drive a stroboscopic transition from this Dicke state to a cat-like state. Our results open a route to ultrafast engineering of macroscopic quantum matter with strong-field quantum light.