Bulk import objects (csv files) into groups

I'm looking for examples of software and best practices around bulk import to groups. To keep the project confidential let's say:

John is a private delivery man. He has 20 deliveries today that are split between 3 customers. His onboard computer automatically creates a .csv file every time he makes a delivery. At the end of the day he has 20 .csv files.

What I'd like to do with our software is bulk import all 20 of those files and group them into Jobs 1, 2, and 3 in the most automated way possible. The driver will still have to manually input some data such as road conditions etc. The user will need to have control over which objects belong in which groups.

Are there any best practices or examples of software that solve similar problems.