(Given that it was so close to Notion, I think Paper is one area where the product vision was on to something good; but they didn't succeed at product execution, connecting customer feedback to iterating correctly on product improvements.)
The problem at Dropbox seems to have been that there was no cohesiveness to all the products. Paper, Passwords, Sign, all seem to have never been truly integrated into a single experience. Each one felt like it was trying to have its own identity.
From Dropbox's perspective, this sounds great. Accounts become more useful and valuable. The addressable market of a Dropbox account grows! Plus, everyone has a Dropbox account already, right?
Unfortunately, it turns out that business customers generally don't deploy Dropbox wall-to-wall. It's expensive. Not all employees need file sync.
A Dropbox account ends up being an obstacle to adoption.
And a distraction: a common account creates an irresistible urge to spend a lot of time finding ways to tie this new product into the old one.
I would also if anything put Zoom in with Dropbox, they have a product that is by far the most enjoyable to use in that space, but any other offshoot is not worth it.
Is the alternative not likely that they would have spent a decade fighting a losing battle over office software with Google and Microsoft? Paper was a great product but the big guys have vertical integration so companies prefer their end-to-end solutions (GSuite etc) and I don't see how Dropbox could have easily overcome that.
Slack, Zoom, and Notion all argue against that. Yes, they have to compete against Google and Microsoft's integrated solutions, but they're good enough that they have held their own. Of course they would be bigger if Google and Microsoft didn't have such products.
