When Don and Bobbie Barrett meet for drinks and dinner at Sardi's, there is a caricature of Jimmy Barrett on the wall behind her, "watching" them the whole time.
While the title may ostensibly refer to Don's new secretary, Jane Siegel, it also refers to the creation of Peggy as a more confident woman. Flashbacks reveal the immediate aftermath of the surprise birth of her baby and show the marked difference between the timid young secretary and the more assertive copywriter we see in this episode.
When Rachel and Don meet at Sardi's , he asks her how things are at Grey, the agency for which Menken's left Sterling Cooper. Grey was a primarily Jewish agency - the same kind of agency Rachel was trying to get away from when she hired WASP-y Sterling Cooper.
When Bobbie Barrett tells Don how she became Jimmy's manager, she says, "This is America. Pick a job and become the person who does it." That's exactly what Don did to get into advertising, and why he responds, "That's true.".
Don is briefly arrested and fined in New York for having a blood alcohol content of .15%. As of 1996, New York had lowered the allowable percentage; any blood alcohol content over .05% will initiate a criminal case