Red Team Career Path: From Engineer to CISO in 2026
People talk about “getting into cybersecurity” like it’s a single destination. It isn’t. The red team career path is a long road with distinct phases, each requiring different skills, different mindsets, and different investments. I’ve spent over a decade in offensive security — from junior analyst writing first-ever pentest reports to leading red team programs and advising on enterprise security strategy. Here’s an honest map of the terrain. The Career Levels (And What They Actually Mean) Level 1: Junior Penetration Tester / Security Analyst (0-2 years) This is where everyone starts, and most people underestimate how much work it takes to get here legitimately. ...