I ended up at Shopify by way of a small startup I was at being acquired. I didn't know much about the company at the time thinking it was basically an ecommerce website builder. I don't think I would have chosen it on my own. I usually go for tech-heavy startups with significant technical challenges whether it's building up the product or scaling it up and the tech plays a large part of my interests. I ended up working at a Ruby/Rails shop once before and I didn't like it at first and got used to it while I was there. The RoR at Shopify is much more structured the way I would expect a good team of engineers would build something rather than a one-off solo dev. There's also a fair amount of in-house tech so it's Shopify-flavored-RoR. This is fine, but all pretty subjective.<p>The parts that I think most would find positive is that the company is very transparent internally with high alignment from executive through development. Management is technically aware for companies of any size and especially for a large one. Most decisions are easy to understand and rarely (if ever, can't remember one) has caused me internal conflict of interests. Regardless of the tech used, I haven't gotten bored or needing a challenge for very long. Each new project presents new challenges, that's left for the team to research, prototype, and build. I spend very little time in meetings, and usually only those I want to addend (e.g. team standups, tech talks, show n tells).<p>Subjective downsides: the company is remote (not '-first' or 'for now', but always for everyone) though team IRL events are +1. The main tech is RoR, MySQL, Go, Redis, Kafka, Elasticsearch. Some groups (e.g. data) use other languages/tools. Of course there's also lots of front-end web/mobile dev that has the challenge of building an extensible platform. Spending time on related opensource work is good. I made some contribs to Sorbet type checker.<p>Long reply, in short I usually leave a startup after 1.5 - 2 years because it doesn't have anything more for me. I'm coming up on 3 years now.