Poor leadership. At the managerial level of the Analytics and Sales departments there is just a lack of strong leaders. Many are first time leaders and their metrics are determined by others that have little to no experience.
At the higher levels of leadership there is also a large gap in communication. Typically bigger picture items work their way down the rumor mill to Regional managers to Sales Managers to Team Leaders then to the Reps who are meeting with clients. This is pretty funny for a company that prides itself on being a "Flat organization." Seldom do the big picture ideas come to fruition, and even more seldom do they solve the problems facing the larger client base without costing them more for the service.
Internal Metrics are god awful. They barely make any sense, and to try and communicate them to the outside world is impossible. For sales reps there is no commission structure and your bonus comes out of a black box so its impossible to know what your year end will look like.
I know I put this as a Pro as well, but let me explain: They discuss how this is a "sales team" but it is more of a consulting role where you are assisting clients with their issues and utilizing the terminal as the solution. This is great because you will learn some priceless lessons about running a business; however, when you sell them something you will not receive the credit. Some deals can be in the 6 digit range, but you will not see a penny of it. Also, there are a number of different departments that scrap for credit, and if you don't document your every call, your every interaction , or if your manager just doesn't fight for you - you will get 0 credit. At the end of the year ,the number of successes determine your pay so these conversations matter even though there is no dollar figure associated with each one. Long story short - you can end up working a lot on a small deal and receive the same credit you would for working barely at all on a large one. Its all about the story you tell which is ridiculous.