I'm with Redsy.

The klein 1412 romex tool is a must have for residential. This tool will pay for itself real fast.

I always remove the sheath before landing in the box for wire inspection and arrangement purposes.

I also arrange my conductors beforehand so they line up nice once landed inside the box (whites next to whites, blacks next to blacks.....) I usually have to flip the romex somewhere before it enters the box to accomplish this but you'll never see that once the walls are closed.