First, the "boring" stuff:
Salary seems to vary wildly, and the benefits package is so-so. Health care in particular is "fine". No 401k matching, which was promised when I joined. Infinite vacation is the real deal, though - in many organizations, infinite vacation means no vacation, but at Toast (at least in engineering) you can definitely take advantage.
Next, Engineering Culture. Toast still operates like a startup, which is incredibly frustrating in an engineering organization this large. This causes thematic issues:
Awards are based on visible output. Getting something done quickly is far more important than getting it done well. Similarly, fixing a problem is better than preventing it.
There is no incentive to solve systemic problems, because when you're doing that, you're not writing features. The part above where I mentioned having flexibility? You have that, but you'd better do it in addition to a full work week putting out features.
It is hard to become productive at Toast. Every company believes they hire only the best, and Toast is no different. The truth is, hiring people with relevant experience is hard, and pretty much every hire you talk to has a story about being thrown into the deep end.
The engineering ladder is very good. If you follow it, you can find a well-specified plan to becoming a better developer. If you want to get promoted, just focus on the row that pertains to output, because the rest of the metrics don't matter to your superiors.
The tech debt is real. For most teams, you're going to be spending a lot of time addressing some choices that were probably justified on day one, and some choices that seemed insane in year four. This is a good skill to grow, of course.
For most people with any prior technical experience, you're probably going to feel underutilized. If you're the kind of person who can cut through the crap and convert free snacks into lines of code, there's a lot of opportunity at Toast. If you hate waiting for a rebuild of your entire software suite only to have it fail because some other team made a bad commit to a service you don't even care about... well, that's how you're going to spend about 30% of your time. I mentioned having very good peers; that is true, but on average this is the least effective engineering organization I've been a part of. You can try to fix these things, but nobody will help you succeed in doing it. This is a leadership problem.
Many people in positions of influence or leadership are there due to tenure rather than experience building software or running software organizations. It's great that Toast rewards its early developers, but it's not great that their point of view is outsized compared to people who may actually have done this before.
In short, Toast optimizes for the cowboy (or girl) developer. If that isn't you, you've got an uphill battle ahead of you, but it may be worth it.
