It’s obviously hard to know exactly what Jobs meant, and sadly he is not here to be able to ask him, but here is my best guess as to what he meant:
In the early days of computing people would sell task managers, file managers, memory optimisers, software to burn data to a CD etc. As time went on, these ‘products’ just became features of the operating system. While it used to make sense for people to own a copy of Nero Disk Burner, over time this became expected functionality of the operating system. Consumers demands for base software change over time - Task managers used to be a product you bought for your OS, now they are just a feature of your OS.
So what do Dropbox offer, I would say it is “seamless file syncing”, which meets a broader consumer goal of “my changes are synchronised across my team and devices”. I think the issue is that as time goes on, this is becoming a standard consumer expectation of applications.
Applications like Google Docs and Figma have actually decided that it’s better if they handle the sync rather than Dropbox. Just like windows was better at task management, they are better at synchronising their own files. It means they can even offer things like collaborative editing!
Secondly, as time moves on, the base expectation for an OS might move to ‘all my files are synchronised’ - and if that’s the case, what is the role for Dropbox in a world where customers just expect that as standard? We used to have file managers as their own purchased products and then they became standard OS features. Why should a cloud file manager or sync service be fundamentally different in a cloud-first world? Online sync might be the new windows file explorer. Take iCloud for example - that’s just a feature fully baked into OSX.
So what does this mean for Dropbox? Well what it offers over time might just become what people expect other software or their operating system to do for them - And I think this is what Jobs was predicting. Why do I have to get something else to sync the files on my computer, surely this is an operating system responsibility?
So then the Dropbox space becomes - “cross operating system syncing of files that don’t have a native cloud sync process”. People still buy Nero Disk Burner... it’s just their market isn’t what it used to be.