Pros
The perks; food, snacks, massages, gym, top-shelf alcohol, cigarette breaks, remote first culture, work if you want, vacation at-will. You can rise from a IP attorney with no business experience to Chief Legal Officer to Chief Administrative Officer to Chief Business Officer in the span of 3 years.
Cons
CEO: Wanstrath is essentially an awkward teenager who lucked into co-founding an incredibly viral product but he has had to do essentially zero since 2008, other than running all the best folks and co-founders out of the company. Wanstrath has never had a higher level job than a line engineer at CNET. The typical brogrammer from the midwest Silicon Valley success story. But behind his auspicious "40-under-40" award lies an incredibly insecure boy who makes decisions in the wee hours of the night with fellow members of his shadow council. His erratic decision making should be a concern to any employee contemplating this shiny unicorn, decisions agreed upon during office hours are 360'ed overnight by Wanstrath. The question is what is causing this very odd behavior. Massive transition at the top, Wanstrath turns on his lieutenants quickly, he is loyal to a handful of "yes" people and anyone who would dare question anything is summarily terminated. Employees live in a culture of fear but the pay is at the 95th percentile and folks just accept the sadly deteriorating culture. Product: virtually no innovation on this front since inception, Kakul is merely a bureaucrat who blasted out of Wework and did nothing for Flickr. Another dismal hire that will not move the company forward. Who else is running the show? scary indeed