I would also add, I think it's relevant the employer never actually asked him to look into automating the process - And it's not even clear they would have want

I would also add, I think it's relevant the employer never actually asked him to look into automating the process - And it's not even clear they would have wanted him to do it or to continue using it if they found out he is doing it. He quite literally just did the work of an automation contractor at the rate of a data-entry person (Or even possibly for free if he did it after hours) without every being asked to do so, so in some ways I have a hard time 'feeling bad' for him in this respect. Before ever writing the program/scripts/etc. he could have told his manager he thought he could automate the process and propose being paid differently (And/or moving into another position or taking on other work once it is done). If they are/were actually interested in automating, they would have likely taken him up on the offer and paid him more or given him a different position, considering it still would have cost less to have him do it then to fire him and hire someone else. And if they didn't want it, then he doesn't do the work in the first place.