Non-equilibrium quantum many-body systems, which are difficult to study via classical computation, have attracted wide interest. Quantum simulation can provide insights into these problems. Here, using a programmable quantum simulator with 16 all-to-all connected superconducting qubits, we investigate the dynamical phase transition in the Lipkin-Meshkov-Glick model with a quenched transverse field. Clear signatures of the dynamical phase transition, merging different concepts of dynamical criticality, are observed by measuring the non-equilibrium order parameter, nonlocal correlations, and the Loschmidt echo. Moreover, near the dynamical critical point, we obtain the optimal spin squeezing of $-7.0pm 0.8$ decibels, showing multipartite entanglement useful for measurements with precision five-fold beyond the standard quantum limit. Based on the capability of entangling qubits simultaneously and the accurate single-shot readout of multi-qubit states, this superconducting quantum simulator can be used to study other problems in non-equilibrium quantum many-body systems.