I have paperwork from the purchase of a 53 Allstate by a Sears employee on 8-7-53 and in a telegram sent to her, it "suggests you contact Allstate Insurance at 808 N Third Street Milwaukee". So, they must have been in the auto insurance business at that point.
Insurance companies like to run at a 96 CR (in other words, for every dollar taken in, 4 cents in left for profit after expenses). Today Allstate is running at about a 110 CR, meaning that it's losing a dime on every dollar. If they keep that up, they won't be in business much longer!