funny you ask that question today because somebody who is also a cyclist was asking me just yesterday and I did some research. I will be not able to assess him myself. So here is a great reference article http://www.active.com/cycling/articles/tight-it-band-3-simple-exercises-… Of course, nothing is as simple as ‘3 Simple Exercises’.
I find hip strength often lacking, particularly hip abductors. And while it may be tempting to roll up and down the IT band with a hard roller, I would combine hip abductor and glute exercises with a soft roller for the inner thigh. The MELT Foot Treatment should also become part of the approach (I saw that you are an instructor).
Has he seen a physical therapist? There should be some recommendations as well that can serve as a starting point.