I don't use Benbox software anymore so I will let someone else help you with that part.
I'll also let @Zax answer for his T2 Laser software, but for BenCutLaser (BCL):
BCL has a very rich feature set for creating letters. You start by creating your text in your CAD drawing (soon BCL will be able to do this internally) and then opening that .dxf file inside BCL.
You can now click on the Text object to select it and there is an EditText link that will popup a text properties dialog window.
On this Text dialog, you have all the fonts on your PC that you can choose from. In the CAD drawing, it doesn't matter at all what the Text looks like because inside BCL you can change it.