Pros
All the perks you need Proactively competitive on salary and benefits, they don't screw around Amazon-like autonomy for individuals Industry that everyone knows, with real people for customers you can talk to in basically any city Strong design sensibility and commitment Strong development/individual growth policy, if unevenly implemented due to weak middle management. Very strong CEO, CPO and COO (IMO), no opinion on CFO and others.
Cons
Some level of constant chaos, between a startup and an enterprise. Shopify is trying to figure it out but failing at establishing a logical, consistent approach to strategy and alignment. Lots of decision by individual opinion; politicking; backchannelling. Politics and cliques among the establishment middle management, e.g. directors/GM's and the people they've carted along with them for a long time-a form of nepotism. Engineering and data are a bit of a mess at an overall level and especially at mid-management, despite lots of awesome IC's and leads.