I find compared to other sports as well that there are far less prominent female NHL reporters or media members. The NFL has some really solid female reporters and analysts although I don't really know any of their names firsthand. Still pretty new to that sport. I've noticed more in basketball as well.
The only prominent female NHL reporter I can think of is Cassie Campbell and I'm not a fan of her work at all. I thought Kristin Reid was great when she worked with the Canucks but she's been gone for a few years now. What happened to Larionov's daughter as well? Never hear her name anymore.
i think cbc/rogers has a couple of of ex team canada players, jen botterill and cassie campbell-pascale
the routes most gm's have taken to get to where they are:
- ex coach
- scouting staff
- broadcaster
- agent
- team or league office legal dept
clearly women can coach hockey, and many NHL coaches dont have nhl player experience, but i have a hard time believing a female head coach is on the horizon, especially since afaik there has yet to be a female assistant coach in the NHL or AHL or CHL or NCAA, places most NHL coaches start off.
scouting staff could be a promising avenue. AFAIK there are no female pro or amateur scouts in the NHL, but there's no reason to believe that there couldnt be at some point. The biggest problem here is that the job requires a massive amount of road time commitment, and even in modern times asking women, often mothers, to accept that is tough.
as i've mentioned, there are female broadcasters. That said broadcaster-to-management is always controversial and again it is a route that requires a substantial amount of time on the road.
the final two routes are most promising... agents and lawyers. These are more stationary jobs that are more likely to attract women, and jobs where being a former nhl player isnt at all necessary. It's perfectly reasonable to expect that at some point a woman either with no sports experience but expertise in labour law turns towards either of these routes, or even more promising a former college or national team player goes to law school at the end of their career and turns to labour law. If the NHL ever has a female GM, i'd bet on it being a former agent or league/team lawyer.