Proposal: The company will support get-togethers to work on specific projects
As discussed with @ernstvn and @stanhu, I think we should be supportive of people who want to get together to collaborate on specific projects, where the co-location will significantly benefit the speed of development, the quality of the end result and allow people to learn from each other in a more direct way.
We are an all-remote company, and we show every day that a product and a company this size can be built with all communication taking place in Slack, Hangouts or the issue tracker, but there are some things that physical co-location offers that these slightly more impersonal channels do not, which become especially important when multiple people, potentially from multiple different teams, are working together on a complex, "greenfield" project where a lot of important decisions need to be made in a short time.
Great examples of such projects are complex features like "Resolve merge conflicts in the web interface" (https://gitlab.com/gitlab-org/gitlab-ce/issues/3567), or refactors of large components of the existing product, like Robert's and my complete refactor of Diff Notes (which we paired on in Austin) or our earlier complete refactor of the Markdown rendering pipeline (which we paired on in San Francisco).
In projects like this, co-location offers a lower barrier to bounce ideas off of each other, immediate feedback to ideas, casual conversations turning into impromptu meetings resulting in great ideas and big decisions, and more rapid iteration when multiple people can pair on something, instead of one having to wait for asynchronous code review and feedback from the others.
We already have a policy where we are supportive of people attending work-related conferences for their own professional development, where the company will cover the first $500, no questions asked, and any further costs will require a proposal and approval by their manager.
I think we should have a similar policy to be supportive of get-togethers that directly translate to value for the company. I have dialed the "no questions asked" amount down from $500 to $300, since there is no conference attendance fee to take into account. In many cases, the total cost of travel and lodging for the get-together will exceed this $300 amount, in which case whoever wants to use this policy should submit a proposal to their manager. The manager will then evaluate whether the project intended to be worked on would indeed benefit significantly from co-location, and whether it makes sense to cover all of, or a portion of, the total cost required to realize this.
I think that being supportive of people getting together to collaborate on specific projects, and having a clear policy around this, will significantly benefit the speed of development and the quality of the end result of these projects where this is warranted.