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The trick to keeping the old-school seatpost clamps working right is to make sure that the OD's of the four toothed surfaces stay concentric as you tighten the clamp, which keeps the teeth fully engaged on both sides.

Before final tightening, I often have to tap/whack one of the circular pieces with a small hammer to force it back into concentricity with it's mating part.
This has to correct on both sides, as each side has a pair of toothed mating surfaces.

Luckily, these parts have those round OD surfaces to give visual (or by feel if working in poor light) indication of toothed parts not aligned concentrically. It helps that these parts seem to be generally made to very good tolerances!
The aligned parts suddenly start working right if everything stays concentric as you do the final tightening.


Another tip when working with these (changing a saddle usually) is to slide out the bolt just far enough to release one of the toothed clamp "ears", then install the clamp assembly to one rail, then insert the loose toothed ear in the saddle and then force the clamp in to complete the "sandwich". Then install the outer ear (without teeth) and push the bolt through, then secure the nut.

I've fitted many hundreds of these things and they don't bother me any more. Oddly enough, I almost always am able to get the tilt to be acceptable, at least within modest standards.