It happens to everyone at different times, there doesn't seem to be any correlation between users. It can happen if all of us are logged in or if only one is logged in too.
After some more playing around, it seems like it has something to do with other applications running on the machine at the time. When looking at the debug logs, it seems like WSAM is always proxying Chrome.exe right before it crashes. Our WSAM policy has certain processes which are allow bypassing the proxy, one such exception is that any executable named apache*.exe is bypassed. I renamed my Chrome's executable to be apachechrome.exe and since I've done this I haven't seen WSAM crash.
I had a co-worker try the above as well and it seems to be working for them too. I'm not sure if other processes will cause a similar crash, but it seems like something about Google Chrome doesn't agree with WSAM and causes WSAM to crash.