Call me crazy, but I don't think a human body moving at the speed of sound outside of a vehicle is a good idea.
It's not a big deal at all for a jump like this. He'll probably just barely go supersonic, and since he's not going to go much faster than that, it means that around Mach 1 his speed will be creeping up slowly and then creeping back down slowly. That means he's not accelerating very much, which means his velocity is relatively constant, which means his body will be near 1G, just like he was laying in bed. The only forces he'll feel are a result of his body weight, since that's all that is driving him through the air. So even though he's supersonic, he's doing it in air thin enough that only a body-weight's worth of thrust is involved, and a body-weight's worth of drag.
It could get uncomfortable if he came in from much, much higher, where he'd be hitting the atmosphere's layers much faster, producing much higher deceleration rates, and thus much higher forces. Or if he was low in the atmosphere, such as ejecting from a supersonic fighter.
He could probably make it much more exciting by jumping out with an ejection seat rocket motor to speed him up.