Pyruvate is negatively charged molecule and highly polar which do not allow it to pass through any biological membrane.
So now comes the question that how it enters outer mitochondrial membrane?
The outer mitochondrial membrane contains proteins called porins, which form channels that allow the free diffusion of molecules smaller than about 6000 daltons. It is suggested that pyruvate traverses the outer mitochondrial membrane through the large, relatively non-specific, voltage-dependent anion channel (VDAC), or porin.
In contrast to outer mitochondrial membrane, Inner mitochondrial membrane is impermeable and does not have such channels. The transport of pyruvate through inner membrane occur by carrier mediated process. Recent studies suggest that two proteins, mitochondrial pyruvate carriers MPC1 and MPC2, form a hetero-oligomeric complex in the inner mitochondrial membrane to facilitate pyruvate transport (Kyle S. McCommis and Brian N. Finck, 2015).