n. An employee, consultant, or third party who uses humor to point out a company's flaws and to suggest solutions.
2001
It was also the case that groups or localities … would collectively appoint a jester — and in this less one-to-one relationship he still exists and is, if anything, in the ascendant. When British Airways appointed a Corporate Jester, he was jester to the company, not to the chief executive; similarly a number of cities are starting to appoint municipal jesters-in-residence — such as Salisbury, Leicester, Oxford, Bristol and Wellingborough.
1989 (earliest)
Donahue would like to see corporate jesters or "humor guys" employed by companies to keep employees loose and happy, and promote creative problem solving.
There was no goof shortage at the Anheuser-Busch booth either, where the Budweiser people's official corporate jester, Rick Gerber, was twisting balloons into little animals and pulling cards out of concealed places.