I think female management jobs will come first. GM, assistant GM, head of scouting etc.
Women coaching and playing in the NHL may take a very long time/require a very special person. There are uncomfortable truths around what I see as necessary aggression and confrontational traits being skewed towards males, particularly so at the extremes.
I think as we bring more women into management the idea of a female coach will be less taboo, and lower level men's leagues may give a few a chance.
If they are successful there, then I imagine some NHL team will bring them in to work through the ranks.