This looks like it could be one of several things.
1. Being that the gap is also left when using the pen tool, I would first look at the overcut value and mess with that while using the pen tool to see if you can close up those gaps. Most machines have a stand-alone software app where you can fine tune things much more than you can through your design/cutting program drivers.
2. Blade depth is set too deep, so when the blade goes down initially and it is pointing the wrong way, it would slice into the edge of the letter before it swivels to go in the direction of the cut. -probably not the case though, since the pen tool leaves a gap too.
3. Double check both the blade depth setup per instructions in owner's manual and the down force settings to make sure neither one is too much.
4. Is it possible that somehow the blade holder arm got bent ever so slightly? From a media jam or whatever?
5. Is there a way to re-initialize your cutter to set it back to all of it's factory specs? Maybe call your rep on that one.
6. Try slowing the machine all the way down and make a circle cut without weeding it. Then have a close look at and you might be able to better see exactly where the blade went down and where it stopped in relation to the starting point.
7. Drink heavily