1. Startup Quirks: Shopify is very much so still a start-up in many ways. Not all processes are well defined, and who owns certain components can be hard to track down. But this also means things aren’t super rigid and bureaucratic. Personally a lot of this I’d still consider a pro, but I didn’t have much else to write here.
2. Internal Movements: Shopify does love promoting people internally, but there are definitely some times when being internal hurts. Usually, if you’re a Guru, since the demand to get a non-support role is so large. There are also very significant compensation discrepancies for internal hires vs external ones, which can suck for people getting promoted.