IMHO, guest users should be free for everyone. Why should I use GitLab Ultimate instead of GitLab CE + JIRA + JIRA Service Desk and even BitBucket? If I have less than 10 contributors (ie: developers), I can self host Atlassian stuff for less than $100 / year and JIRA Service Desk lets me have unlimited customers for no additional cost.

GitLab's issue tracker and Wiki would be a perfect fit for me to support customers and non-contributors. I really think you should try to make that type of distinction. I would describe a "non-contributor" as someone that generates work for contributors. Ex: Customers submitting issues that a developer needs to fix.

I don't understand the reluctance to make guests free for everyone. If you're worried about existing licenses getting dropped in favor of free guests, you've got a big problem that's going to catch up with you eventually. People don't like paying for things they're not using.

If you think free guest users will encourage people to upgrade, I don't like that either. It's really frustrating to get locked out of features that would be useful to me just because I'm not a huge developer that can afford Ultimate licenses. I'd say that limiting my ability to develop good processes and workflows, as a tactic for "encouraging" me to upgrade, isn't going to leave me felling confident in my choice to use GitLab. Giving me the ability to scale up when I need it / can afford it will.

I want licensing that scales up with me, not licencing that I need to buy if I want to scale up. Get it? I'm already making a HUGE trade-off to move from CE to a paid license because I can't add contributors for free any more.

As a general observation, the way GitLab's cost scales up seems weird to me. If you plot the incremental cost of adding users to (ex:) JIRA, it looks like a hill that gets easier to climb as you add users. If you do the same for GitLab, it looks like a set of stairs (aka steps). Every time you jump tiers there's a huge pricing cliff you need to be able to climb. If the features I need to scale up (my business) are locked behind those pricing cliffs, I think it's risky to buy into that, isn't it?

I really like the way Microsoft does their licensing with Office 365. They let you arbitrarily assign licenses on a per user basis. For example, I can have one user on "Business Premium" and everyone else on "Business Essentials". Have you ever considered something similar?

I feel like I get really good value out of the Office 365 model. To use GitLab as an example, I "make do" with "Starter" because I don't want to bear the cost of an upgrade for every user. With Office 365 I'd simply buy a "Premium" license for myself and leave everyone else with "Starter" licenses.

I would also say that if you ever decide to allow arbitrary, per-user licenses, the first user should get a free Ultimate license. I've used GitLab for 2+ years and I have no idea what features are available in Ultimate. I pretty much live in CE / Starter. There's no way for me to discover the features I don't have.

I'd also be willing to buy short term licenses, if that were an option, which is another reason guest users being free for everyone might be a good idea. For example, if I'm working on a project for 1 month, it would be nice to be able to give a few people access as collaborators / contributors. However, I don't want to "kick them out" once the project is done, so a downgrade to a free guest user would make a lot of sense. As it is, there's no chance I'm buying licenses for anyone because it's annual only pricing and kicking them out when the project is done makes it seem like I don't want to support the project.

To add something positive, the GitLab (product) issue trackers are amazingly well run. I've never run into a problem with GitLab where I felt like it wasn't worth my time to create an issue for it.