2 Big ones: First, the way we get comped and promoted is a nightmare to figure out. Quit worthy even. The first line of the compensation wiki PAGE says "provide a compensation structure that is simple, transparent, and rewards over-performance". The 4K word explanation plus dozens upon dozens of questions proves that it is neither clear nor transparent. There's gotchas, claw backs, this counts for this not for that, it's ridiculous. You gotta do this + that, and you get this, but if you sell this + that under this time period you only get this, add this, divide by this, multiply by that and, well, is your head spinning yet? This really needs to get simplified. It's hard to always solve for the customer when you're also trying to not shoot yourself in the foot.
Second, there is no continuous training, not just from a sales coaching/development perspective but on the product in general. It's awesome that we're always innovating on the product, but when there's no structured/programmatic training to keep up with these changes, selling can get tricky. One offs are not going to cut it. Training at a team level is not consistent either