corporate jester
n. An employee, consultant, or third party who uses humor to point out a company‘s flaws and to suggest solutions.

Example Citation:
"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."
—Beatrice K. Otto, "Fools are everywhere," History Today, June 1, 2001

Earliest Citation:
Donahue would like to see corporate jesters or "humor guys" employed by companies to keep employees loose and happy, and promote creative problem solving.
—Peter Gorrie, "Workplace humor is no joke to new generation of jesters; Consultants demonstrate how humor can improve atmosphere, performance," The Toronto Star, November 3, 1989

Notes:
A different sense of the phrase — a comedian who performs at corporate functions — is a bit older:

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.
—Judi Dash, "Looking for a dreamboat," The Record, January 15, 1985

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