Rashaan Green’s story at Second Front reminds me why I tell candidates not to apologize for unconventional backgrounds. The cleared community still defaults to pedigree—service academy, Big Five consulting, the usual tour—but some of the sharpest cybersecurity leaders I’ve placed came in sideways. They learned to translate between worlds, which turns out to be the skill that matters when you’re trying to move capability from commercial tech into a defense buyer’s hands.
The hard part isn’t the transition itself. It’s convincing the hiring executive that different doesn’t mean risky. I spend half my time in retained engagements mapping passive candidates who check every box, and the other half making the case for someone who checks the right ones. If you’ve built something that works in a commercial environment under constraints—budget, speed, scrutiny—you’ve probably got more to offer a program office than someone who’s only ever operated inside the castle walls.
That said, you still need to do the work. Get the clearance. Learn the customer. Show up with a track record, not just a theory. Unconventional gets you in the room, but delivery gets you the next call.