What has to happen is a gradual lengthening of the AT
by progressive stretching - hence the exercise I recommended.
Also, direct pressure (as much pressure as creates mild discomfort not pain)
massage, with ice if sore and inflamed, stroking upwards from the bottom of the
heel through the lower calf, is beneficial in reducing the inflammation.
Do that immediately after your cool down and after your stretching. As
Beverly said, it is the repetitive damage that builds up and leads to real
issues. Don't ignore this as it will get worse, not better.
As a riding instructor, I teach my students to "raise their toes" rather
than "drop their heels" when they ride. I find that many folk "drop their
heels" by forcing them down - or bracing through the hamstring, straightening
the knee and over-stretching the calf down through the heel. By
instructing them to raise their toes they actually relax through the leg, keep
the knee bent and soften the stretch through the calf and AT. Don't know
if that makes sense, and don't know if, in your case, that it would work, but
you could try it to see if the pain is eased.