Five bucks per person-month doesn't make sense in either market. It's $5 too much for people building their business on Drive and Evernote. It's too little for 10,000 screen organizations...they know you will go broke. And then there's an asterisk on the free plan and another deal for students, so I'm left wondering if it's worth figuring out the value proposition before I think about learning how to use it.
If it was an enterprise product, it might make sense but that's not live fast. die young, and leave a good looking corpse business strategy compatible. Students probably don't need mobile task updates for group projects. In the middle, though, there are good user stories and price points. $400 per month for up to 20 users...that sounds like a way to qualify businesses and reduce the number of sales.
And if you can't make the bottom line $5000 per year better for 2000 companies, then it's time to throw in the towel.
Good luck.