When I was learning toeside, someone here on WW gave me the following advice, which really helped me out:
1. Do a normal heelside jump, then come back across the wake toeside. Don't try to jump, just travel across the wake.
2. Now, in order to get out and do another heelside jump, you normally cut quite hard to get out there. As you start cutting, analyze all the things you are doing:
A. Standing fairly straight/tall
B. Maintaining solid pressure on your toeside
C. Leaning 'down' the rope.
D. Cutting like you intend on carving the next 30 feet without stopping.
Now, after you practice that for a few times, apply the exact same principles, but instead of carving away from the wake, now set up so that your carve is approaching the wake.
The 'lean down the rope' is the most important thing for me. I was always trying to lean into the wake. You need to lean 'away' from the boat to get the line tension necessary for good pop.
Sorry if that was convoluted, I reread it and it sounds like mung, but I don't want to retype