I’d say the biggest obstacle is that a requisition for someone at your level is just really hard to get. It’s hard to convince people that we need an expensive

I’d say the biggest obstacle is that a requisition for someone at your level is just really hard to get. It’s hard to convince people that we need an expensive gray beard. Without a requisition at your level some companies have a policy that they won’t talk to you because they don’t want to leave you with a bad experience (sounds like bs but this is true). The view isn’t entirely just financial. People at your level challenge things and in particular challenge leaders. That’s because you should be a leader at this point, either by title or by influence. Someone like you can come in and disrupt the power dynamic, particularly if the leadership is weak (often true), and the leadership wants nothing more than to preserve itself and make its life easy. Another piece is the more senior you are, the more the soft skills come into it and how well you’ll fit into the team. I’m not talking about skinny jeans here but rather whether your values align. If you are trying to get VP of Engineering jobs, I’d say that few would believe that you’ll be satisfied just coming in and grinding out walls code to a spec that someone else wrote.