[throwaway11460]

Because he is paid to do so, not to keep his own job cushy and safe. Sometimes you're paid to automate yourself out of a job, sometimes you're paid to let someone take over - don't take the money if you're not willing to do it.

[heisenbit]

Who pays? Your boss gives directions but there is a reason for companies having values and missions. Companies interest and instructions received not always align. Particularly when it comes to outsourcing paying attention to incentives of individual decision makers is important.