Great for ICs, bad for managers
Engineering Manager (Current Employee) – Boston, MA – February 16, 2018
Toast is a great startup, with the relaxed-but-busy environment you'd expect. As a software developer, there are challenging problems to solve, great senior developers to learn from, and friendly coworkers that you can form a social social with, or not, as you like. Toast has also made a concerted effort to attract women in technical roles, and the fact that it wasn't an old-boys club or frat house was a refreshing change from other places I've worked.
Unfortunately, like many fast-growing startups, Toast was founded on a "get stuff done" principle. And, like most startups, Toast is having growing pains trying to scale that mentality from four people in a basement to a company of a thousand. The founders still want to be deeply involved on a tactical level, and the existing middle management has not been able to successfully steer the founders into being able to focus on the strategic level.
Also, like most companies new to working at scale, the communication channels are starting to get clogged. There's often a feeling that things which seem obvious to product managers and software developers on the ground aren't being heard by VPs and Presidents, and that the verbal expression of culture no longer matches up to what's valued in practice.
Having said all that, Toast does way more right than the average Boston startup, and I'd go back in an instant for the right opportunity.
A real sense of fun, good ad hoc social networks, interesting technical challenges
"Write lots of code" is the only true metric of success, the product-engineering relationship isn't getting better, execs can get mired in tactical decisions