There's a couple of general points though that I'd love to comment on.
> Why can't I just SSO using my GitLab credentials into Zendesk?
I'd love to have this as well - it makes complete sense (especially for our SaaS customers - it wouldn't help as much for self-managed). In order to get it implemented we need GitLab.com to become a SAML or JSON Web Token source. We have an open feature request for that here: https://gitlab.com/gitlab-org/gitlab/-/issues/238419
Even with that implemented we'd still have some challenges identifying who should be getting support without occasionally asking for proof of a support contract. As you said, you're part of multiple GitLab groups. It's well possible that some of those are on our Free tier and others on Paid tiers. In some contexts you'd be eligible for Support, and in others you might not be.
Usually this speed bump only hits the first time you contact support. Once you've opened a ticket we'll have you linked up correctly.
Recently I've been working on improving contact management and making sure customers are aware of what they can do to make their first support ticket the best experience it can be. You can track that effort in https://gitlab.com/groups/gitlab-com/support/-/epics/156
> Why use terms like "Support Entitlement" – just say, which org/group are you with?
We have to consider both our self-managed customers and SaaS customers with our language. For GitLab.com customers naming a path completely works (and is one of the ways you can prove your entitlement: https://about.gitlab.com/support/managing-support-contacts.h...). For Self-managed we have to map account names exactly and need a bit more as some organizations have visibility of tickets between users, in which there may be sensitive data.
I think you're right that it could sound more human. I've opened up https://gitlab.com/gitlab-com/support/support-team-meta/-/is... to discuss improvements.
If you have any thoughts, feel free to participate!