Unique opportunity, with probably more upside than downside
Pros
It's hard to exaggerate the quality of the people that you will work with at Toast. Even through extraordinary growth, you can count the number of people who detract from the overall culture on one hand. In engineering in particular, there are some real stars that are great role models for how to be an effective engineer. I'd also take the position that individually, my coworkers were more competent than I'd experienced in other companies (more on the flip side of that later). Additionally, there really is no "useless" or busywork at Toast. There's a ton that needs doing, and everything you do will manifest in the product somehow. If you want to go somewhere you can just knock out features, Toast is the place for you. Further, it's a place where if you see a problem, you're generally given a lot of flexibility to fix it (there's a caveat here, see "Cons"). In the realm of technical debt, there are and have been initiatives from the top to solve some of the most egregious offenders. The opportunity at Toast is real; I expect the company to continue to grow and improve the product at a steady pace. Finally, Toast treats people like humans. The company is flexible about your goals, desires, and personal life. They make one of the most effective efforts I've seen to improve and discuss diversity (always room for improvement here, though). The hardest part of leaving is losing the opportunity to see these people on a day to day basis.
Cons
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.
