I wouldn't force memorization either. I let my own child use a multiplication table for conceptual math. And then let him play computer games to drill the fact. He has them down now at age 9 through no effort of my own. For the record, we homeschool full time.
Here's a website with a bunch of math games. Timex attack was a big hit at our house too.
http://www.arcademicskillbuilders.com/What curriculum are you using? Many curriculum have placement tests if you think you may not be working at a high enough level. We used Singapore with my child and I didn't force him to do many repetitive type problems. But we spent lots of times doing multi-step and word problems which I think really cement the concepts and teach organizational and logic skills. At age 5, I wouldn't force anything and if she lost interest I'd back off totally.
