Pros
You get to work with some amazing people OUTSIDE of leadership.
Cons
The leadership - from the founders to the executive team. The heart of the issue of the organization starts from the top. So many talented/experienced people have either been let go or left. There is no organizational (product or operational) vision from the founders other than throwing people at the problem. The CEO is about as disconnected from the rest of the organization as you can imagine. Sales runs this place and his little to zero disregard for anyone that functions outside of that department - super toxic org that is constantly creating a hostile cross functional work experience by escalating everything to the top with ZERO solutions - the complaining is off the charts. Overselling and under deliver is their motto (probably due to lack of understanding of the business). Ops gets the blame for extreme product shortcomings. Product spends close to zero time shadowing ops. The only people that are left here are either blindly loyal, can't find a job anywhere else, or are pretty much "yes" people. Work/life balance - what balance? It's pretty messy here. Investors may have laid an egg here... but hey it's just another one bites the dust, right? I'm sure Sequoia has plenty of rockstars in their portfolio left and plenty of capital to find a winner somewhere else.