Pros
Really solid product when it works (a lot of scale issues lately), solves a genuine, painful industry problem. There are some seriously good people in there. Probably the best engineers I've worked with were here, although most are gone by now. There probably are some good teams outside of engineering. The VP of Customer Experience seems to know what he's doing, same for the CMO. But if you're in engineering, you may want to stay away until they figure their stuff out.
Cons
Impressively terrible CEO, who rules by fear and control, and has basically zero people skills, and no understanding of how successful tech companies work as he's never worked for one before. Unfortunately, he hires C-level leaders who mostly have the same traits and fits his world view (even if sometimes they do know better but eventually give up pushing back). He has a strong understanding of the industry and customers though. Engineering is ran like a consulting shop, with product ordering engineers one-by-one what they should work on each day of the next few months; and engineering being blamed when obviously that doesn't work to ship the intended value or more in the force-committed time. Very dis-empowering culture, set up for engineering failure, with no accountability on anyone else in the product-building cycle. There used to be a time where it was the opposite, engineers were empowered while being made accountable by their VP for their results. At that time, projects were turned in mostly on committed time, value was being delivered at a very fast pace, and the platform was more stable. Then the CEO cracked down on this for the sake of his control over it, completely ignored the warnings being given by his senior engineering staff who had more experience at it than he does, and as a result 90% of all engineering management (including the VP Eng) and senior+ engineers quit in the span of 6-9 months. So disheartening what leadership incompetence will do...
