Your issue won't be finding a job- it'll be keeping your medical/pilot certificate after not reporting the first one and then getting another one.

Definitely talk to an AOPA lawyer. Chances are you'll need to report both arrests to the FAA with a full write-up of the situation, including police reports/court documents, a personal statement depicting why you think the FAA should issue you a medical/and or pilot certificate, proof of some sort of successful rehab or alcohol abuse program, and loads of other requested documents.

You will probably lose your pilot certificate for lack of reporting, but it could possibly be reinstated in a year...but then there's that pesky medical exam, which will be hard to get. A medical examiner is required to defer your paperwork to the FAA with two DUIs/arrests/convictions.

You need an AVIATION attorney and a lot of patience. DUI/DWI medical waivers tend to slip to the bottom of the priority list at the FAA. It'll take a while, so I suggest you start the ball rolling soon.