Pros
Playboy is a company that has some really great benefits. The parties and the lifestyle are very cool.
Cons
One of the most poorly structured companies I've ever worked for. More VPs with silo'd divisions unwilling to cooperate with each other for fear of being proved incompetent. One of the most hyper-political companies with an incredibly talented staff most set up against each other instead of united in common goals. MBA textbooks written in 1985 could prescribe fixes to these organizational issues. Senior management has been looting the place for years which resulted in near bankruptcy that was staved off by allowing a private equity firm to take the company private and sell off or license every division. Understandable, but awful to work for. Playboy has basically eliminated or outsourced most of their workforce. Much of the company is run by the Canadian porn company Manwin.
