I was the entire IT department at a small company. (Maybe 50% development; the rest management, sysadmin, and support.) I was pretty sure I could convince my bosses to allow it, since I perform well and am hard to replace. The only hard part was finding someone to share my job with me, because my bosses didn't want to increase my budget. Luckily someone in my network liked the idea, and now we share a job.