This question already has an answer here:
In this video
you can see a logo next to head that moves with it.
How can I do that in Premiere?
This question has been asked before and already has an answer. If those answers do not fully address your question, please ask a new question.
This is called Motion Tracking. You define a part on the head that will be tracked, and then have another object move relative to this position.
I'm not sure this can be easily done with Premiere, as I've never done that, but it's a fairly standard procedure in After Effects. After Effects has a built-in tracking system, but there are also plugins like Mocha which offer the same features (and possibly a bit more).
There are hundreds of Motion Tracking tutorials online that explain how to do this, but looking for the term "Tracking" should get you started easily. For example, here's a tutorial for Premiere: