I think it's more effective, and feels more natural, when individual staff voices who have the user-facing skills do this. But of course they don't all have the knowledge and authority to address all issues, from money to editorial to tech.
Ideally you would have one 'Locutus of Medium' in each area as delegated touchy-feely spokesperson, reaching out regularly.
Zulie Rane is a welcome addition to the staff - she feels more like 'one of us'. But then I guess Tony Stubblebine did back in the day, and he seems to me to have withdrawn into a somewhat defensive corporate shell. That goes with the CEO role a little, and maybe it's just his manner, but I also suspect that corporate lawyers play a role in stifling frank sincerity at US companies. 'Don't apologise! Their lawyers will take that as an admission of liability and sue us!'.
US litigation culture has a LOT to answer for in the modern world. But I'm going off on a tangential rant there.