He would have to pivot or extend. Suggestions to extend on paper:

* graduate degree

* PMP and/or CISSP

* federal security clearance

* foreign language

* certs for AWS/Google/Azure

Technical pivots:

* operations (PMP would be helpful)

* management. I have pivoted to management and operations but am still required to ship software as a developer

* cloud infrastructure

* enterprise API management (MuleSoft is a proprietary solution that seems to be the growing industry solution)

* network management - routers and switches (get a CCNA and then work towards a CCNP)

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The best part about getting into a high barrier of entry job is the people. Everybody is generally confident about their ability to execute. That means people are more honest about technical concerns, less focused on how to do their jobs (literacy), less focused on the vanity of the technical work, and are generally more pleasant to be around.