Yeah, I can see how having to engage with senior management would be anxiety provoking. I feel your pain! Sometimes I have to lead solutioning workshops with SMEs across diverse domains. It can be nerve racking! My 35 year career evolved from network engineering, to security ops, to security engineering, to security architecture. I essentially design and deliver security solutions for an organisation. Being a Pen-Tester, you have solid knowledge of attack vectors and methodologies, exploiting vulnerabilities in protocols and endpoints etc. You can gradually move into security engineering, then solution design, then into architecture.