The questions should be answered by all the devs in the hiring team. You don't care about the compatibility between HR and employee, you care about compatibility between your peers and your direct boss.

> I can't think of any "normal" person I know that looks for jobs without some negative catalyst pushing them into it.

You can also solve it by making the match between team members. This way, companies could even ask their currently employees to participate, which means that people would be using the website even if they are not looking for a job directly.