Hi Karen
It is possible to upload users and courses for enrolment in the one file using Upload users and including the user details and course code. You won't be able to update any of the job assignment information using this method.
If you are wanting to add the job assignment information then HR Import can be used to add users and dynamic audiences used to automatically pull users that meet a criteria such as a date in the user table and enrol then in courses through the enrolled learning tab of the audience.
Regards