Sounds like he's lucky though. Many companies are happy to let you specialize in their area of business, own the special software, get to know all the vendors & business contacts then really not pay you well. You dont get to find out until 5 years in when you have skills that aren't really transferable to a new job.
His skills are quite transferable. Many of the company’s customers would love to hire him away. The company doesn’t have a noncompete, and he’d probably quit, if they tried.