Pros
Toast is very likely to be highly financially successful. The founders hit the market at exactly the right time, and have built a very successful go to market engine. There are a lot of good people in the organization as a whole. Mid-management is pretty good, and tons of talented, hardworking folks on the front lines of every part of the org. Comp is fair, and stock is likely to be very valuable.
Cons
Working at Toast is really not great. Leaders are all over the place and totally sub-par for an org of this size, very unprofessional, poor at management, and poor at making tradeoffs and setting priorities. They set high goals for the org and meet them in terms of GTM (again, this is because of market dynamics mostly - competition is pretty lackluster in the industry, and cloud software is taking over). But the high goals in other areas that are actually much harder and require real management skill and experience - eNPS, cNPS - are total misses. The lack of professionalism and cohesion in the leadership team is astonishing, and has ripple effects throughout the org. Leaders are incentivized at cross-purposes and duke it out by sending mid-management to squabble with each other in cross-functional initiatives. Deeply, deeply inefficient and frustrating.
