Just to get used to it, try letting go of the handle with your rear hand, leaning your whole body over, and dragging your rear hand through the water. Don't bend at the waist when you're doing this and keep fairly even pressure on both of your feet. That should get you way out there.
Keep in mind, however, that you don't need much of an approach to get air. If you can wait for the rope to tighten up, grab a good edge, accelerate quickly, and stand tall at the wake, you can easily clear the wakes, with plenty of air, from only 8 or 10 feet outside the wake.
Tim's question about speed is also relevant. If you go too slow, your board will feel very sluggish and edging will be tough. Try to go at least 21. 23 is even easier but it's much less forgiving if you fall. If you don't have a properly calibrated paddle wheel speedometer, try to check your speed with a GPS receiver. Your average boat speeodmeter is not very accurate at all.