The Bigger the Better
Very rare1.5%All-the-thingsOptionalAnywhere
Special Transport
Complete delivery of all oversize cargoes (requires Special Transport DLC)
There are 10 different oversized cargo types in the DLC - just complete one job of each kind. You'll get Size Matters for the first one.
The "Haul Truck Chassis" cargo will also unlock Big Brother
Oversized cargo appears in the job list with red/white striped line down the left side - its hard to miss them, but you might need to travel to get to a departure city to take a job.