After spending 15 years in security at a mid-sized DoD contractor and starting a job search as a security architect, I thought finding a new job would be easy. After all, we are told that there are “more than 1M vacant cybersecurity jobs in the U.S.” My journey was far from easy; resume edits, pitfalls, miscommunication, and unclear job descriptions resulted in failed job search after failed job search. The job searching process forced me into communication with recruiters who didn’t speak security and resulted in interviews for any and all security positions, thus wasting everyone's time. The compilation of job searches created an abundance of self-doubt and not the shiny new opportunity for which I had been seeking.Fast forward to today where I am the Cyber Security Architect for CyberSN, a cyber staffing firm. My confidence has been restored, and I have gained valuable insight into how the staffing process has been systemically broken for a long time. During our presentation, Deidre Diamond (CyberSN Founder and CEO) and I will share my story and provide first-hand examples of obstacles that led to a miserable jobsearch experience, a common theme among my peers in the security industry. We will offer insight as to how this breakdown occurred and how it could have been avoided. We will provide key information, tactics, and advice to self-market, evaluate recruiters, ace the interview, and successfully negotiate salary.