Pros
The people are great, everyone is smart and driven. The location is hip and the office nice, however the neighborhood as a whole is so-so, depending on your take on Venice culture as a whole.
Super stocked fridge, kegerator, and the HR/Office staff really do strive to make a great, welcoming space. There were some fun events too, and hosted some good meetups. Props to them.
The place is just filled with talented, laid back people that I enjoyed being around and collaborating with on a regular basis. Everyone knows everyone and what they do.
When I was there, the dev team was great and keyed in, super productive for how bad the codebase was.
Cons
I worked at Stack for over a year, and the biggest issue is the lack of a Technical Co-Founder (Or balance).
At minimum, there should be a founder that understands development and developer culture. I and many other developers don't feel their contributions are valued in any way other than a tick mark on a feature sheet.
Because of this lack of knowledge and respect, the dev team is a turnstile of both contract and permanent developers. They brand themselves as a Technology company, when the tech is more of a means to an end of augmenting a mediocre platform, than a core business value.
The CEO is very in the weeds, commonly fancying himself a designer, a dev, a marketer, instead of living at 30,000 feet and promoting vision and delegating to people who are much more savvy in those areas.
How do you resolve a problem when the problem is the one and only founder? It's an Emperors New Clothes situation
The benefits look good on paper, but when you try to leverage them, you get guilt tripped for it or you have to really fight to get them.
You're expected to work a ton for less than market rates, and I honestly feel the "unlimited vacation" is really just a way to not pay out PTO when someone leaves.