Pros
It's easy to skate by when nobody around you, especially senior leaders, knows what he/ she is doing. If you're lucky enough to be considered "high potential" (a label bestowed to only marginalized demographics or those able to check their values and dignity at the door) you'll have no problem hiding your ineptitude.
Cons
Senior leaders (especially the C-suite) are just Wall Street deal guys with minimal operating experience and, as such, have little idea how to efficiently operate a business. Vail Resorts grows revenue primarily through resort acquisition, but the company isn't leveraging its scale to the fullest extent possible and inefficiencies exist everywhere. This is especially true of the corporate functions -- e.g. Finance, Shared Services, Marketing and the call center). In these functions in particular, people are in charge simply because they blindly smile and nod at their boss' inane ideas or unrealistic plans. Knowledge and experience are in short supply with this group, resulting in a chaotic environment where nothing gets accomplished and employee churn is unsustainable. Making matter's worse, leaderships' arrogance and pride prevent them from accepting that others in the business, people actually operating the business, may have knowledge on how to run things more efficiently. As such, there is little hope for change and organic growth of the top or bottom line will be much less than they'd be if the company let operators do what they do best: i.e. implement enterprise technology, develop intelligent employees (and pay them a competitive salary so they stick around), implement efficient and scalable processes, and leverage data to gain insights which, in turn, increase efficiencies and the bottom line. Overall, Vail Resort's is place where blowhards and yes-men thrive and anyone with expertise and a spine sees their career stunted.