I used to annoy people (I imagine - certainly Guido never liked the term) by insisting that Python needed marketing. The PSF could, perhaps, extend its outreach efforts to sponsors by trying to overcome the perceived barriers that you mention here.
If we could find some way to make Python support a way to gain kudos in the corporate world we could perhaps find chances to expound the real benefits of open source collaboration. Would it be worth my making inquiries with the Foundation, or am I just dreaming?
“You may call me a dreamer …” – John Lennon