The title is based on the title of the film The Man in the Gray Flannel Suit (1956), starring Gregory Peck.
While checking out Sam's new office, Cliff says he "wouldn't take a job as a window washer for all the bridges in Bridgeport.". He is referring to Bridgeport, Connecticut, which is where John Ratzenberger (Cliff) is originally from.
Per the placard on his desk, Sam's "newly created position" at headquarters is Eastern Regional Sales Manager.