Where does one start? Your userform is called 'contractor' and not Userform1 so it is never called and produces an error. The userform has no action button to write the values from the texts boxes, which are in any case duplicated with overlaid text boxes. Your macros have typos in the VBA commands. VBA is very strict on spelling accuracy. The bookmark you are attempting to write to doesn't exist. The blue button is superfluous unless you want to use it to call the userform again, in which case the command associated with it should be
Option Explicit

Private Sub Document_Open()
    Contractor.Show
End Sub

Private Sub Process_Click()
    Contractor.Show
End Sub
You need to add a pair of command buttons to the userform and then the code in that form is (for one text box).

Option Explicit

Private Sub CommandButton1_Click()
Dim Contractor As Range
    On Error Resume Next
    Set Contractor = ActiveDocument.Bookmarks("contractor").Range
    Contractor.Text = TextBox1.Value
    ActiveDocument.Bookmarks.Add "contractor", Contractor
    Unload Me
    Set Contractor = Nothing
End Sub

Private Sub CommandButton2_Click()
    Unload Me
End Sub
See http://www.gmayor.com/Userform.htm which covers the basics of userforms.