As a former admin, I don't think I ever interacted with anyone from WMF. As you probably know, deletions, locks, bans, bot approvals, etc. are normally handled by volunteers. Even requests for adminship are discussed by volunteers, then finalized by volunteer bureaucrats.

I would say the culture you mention was bred in very early days of Wikipedia. Editor activity peaked in 2007, when the annual budget was ~$2m. The prior year was <$800k.