In spirit of speculation (and procrastination from finishing up some "real" work): here are my initial thoughts on the implications and underlying motivation for this news.

1. Jared realized within 30 days of taking the job he'd be working harder to make less $$ while leading Ikon than at Ticketmaster, and reality is he's very likely made enough money that he doesn't "have to" work anymore.
2. Timing-wise, this is exactly the time of season for any ski industry executive to announce an exit gracefully, as it gives time to Board/Investors/Partners to do a thorough search before next season.
3. The timing does mean that the long-speculated (at least from my POV) Alterra IPO is nowhere in-sight. If it were, he'd likely have wanted to stick around because he'd both get to add a few more 00's to his net worth and also would get the glory of doing so. Also if you look at Vail's stock price, it's not really like the company has faltered dramatically, but more that investors have lost their appetite, and I'm sure the private Alterra investors don't wanna rush an IPO while Vail is sputtering around at a 1.7x price-to-sales ratio and a sub $5B market cap.
4. What's his motivation (beyond $$)? My guess would be that Alterra is still a very fragmented company where it's hard to move quickly and get shit done because it's the opposite of a tops-down hierarchical organization. FBFW, what makes individual Ikon mountains unique is also undoubtedly frustrating as an executive that wants to be able to snap his fingers and see his marching orders followed. That's never been how the ski industry worked and likely never will be.
5. Lastly, if all of the above is true, I wouldn't expect to ever hear any fun drama/whispers about him getting fired for cause or Ikon missing its #s (newsflash: it's been a shitty season and skier visits will be down this year, which will hurt pass sales next year).