When I started shaving about a year ago, I started with the headblade. I have been using it ever since and love it! On the back of my head i go against the grain and it seems to work fine for me, although the back of my head is fairly smooth. I also shave in the shower. (the hot water softens the hair and opens up the pores making it easier to get a smooth shave)
Just remember to go lightly, NO PRESURE!!!! This is the key to using the headblade properly. I do my whole head with my headblade and then go over some spots that are hard to get against the grain with the headblade with the razor i use for my face. For me this is at the back near the top at my cowlick ( I also have a small dent in the back of my head there). and on the sides near the top where the hair grain changes direction. I tend to get some razor burn around my ears so I use a bump eraser spray. (I'm not even sure who makes it but I'm sure you can find it at any local drug store around the shaving section). Try using a pre-shave scrub. This will get rid of any dead skin cells and also opens up pores and softens the hair.
Hope this helps you!