I think it will stick to rough fiberglass. The glue on the back side of good velcro has some serious stick.
I drilled the hole in the lid, then passed the wire through, then cut a rubber grommet and dressed it into the hole.
I added a small dab of marine goop to seal it up.
BTW I just took this shot of the box while the yak was hanging upside down from the rafters. The box stays put unless you remove it.
