State-of-the-art optical lattice clocks are now operating at or near the standard quantum projection noise limit. This limit arises from the independent projection onto the clock state basis of each of the atoms used to reference the local oscillator. Introducing entanglement between the atoms by spin squeezing can reduce the uncertainty associated with these measurements. We analyze spin squeezing via Rydberg dressing in optical lattice clocks with random fractional filling. We provide practical considerations, approximate analytical expressions, and empirical fitting functions to aid in implementing Rydberg-dressed spin squeezing. We demonstrate that spin squeezing via Rydberg dressing in optical lattices can significantly improve clock stability even in the presence of random fractional filling.