I worked in the OriginPLUS team, writing online help for the OriginPLUS development tool used by the IT department to develop their workers compensation application.
I used Microsoft Word with macros to create the WinHelp codes, generate RTF and fed them through the WinHelp compiler. The WorkCover IT programmers were my customers and I got pretty quick feedback if my help content wasn't easily understood.
I think I wrote a few paper manuals to start with, until we abandoned them as being too cumbersome. The online help was context-sensitive so that wherever the user hit F1, the right help page could open up.
Other documentation projects, some of which were done for the PR department included:
Safety Achiever Bonus Scheme
Exempt Employers Scheme.
I also got roped into doing various brochures, presentations, banners, etc.
I even wrote the IT department monthly newsletter, called Floppy Bits.