"Gradually Rip the Band-Aid Off": An Air Force Cyber Officer on SkillBridge, Tech Interviews, and Today's Job Market
Veterans in the Park
Benjamin Fiesel spent about five years as an Air Force cyberspace operations officer, working in software development, Department of Defense acquisitions, and cybersecurity risk and compliance. He separated as a captain, completed a Hiring Our Heroes SkillBridge fellowship hosted at Google in New York City, and now works at Scale AI. He calls the move relatively smooth — and still full of unknowns.
The through-line of the conversation is planning. His biggest lesson from the Air Force is to map a five- to ten-year outlook on the day you join: what you want to achieve while serving, and what comes after. He explains why he left when he did — as an officer, the hands-on technical work he cared about was only going to shrink — and what made the transition hard: being the only earner in a military family, a spouse's career interrupted by moves, and a tech job market that had cooled sharply since the post-COVID hiring boom.
He is candid that his path was easier than most. A computer science degree and contracting experience transferred directly; a combat-arms background does not. His advice for everyone else: pursue the opportunities inside your branch, including the DoD software factories, and cross-train while you still can.
On mistakes, he is direct. The costliest one is waiting too long. Retirees should start two to three years out; anyone on a contract should give themselves at least eighteen months. Competitive civilian roles also demand real preparation — specific stories, a known tech stack, interview practice — and contracting or GS positions can be a useful first step, a way to "gradually rip the band-aid off" before moving to a private company.
Host Charles, a Marine Corps veteran, closes on the habit many veterans carry out of uniform: waiting for the next order instead of reaching for the next opportunity. If you have a separation date on the calendar and no plan yet, start here.
Loading