CareerPlan

Lead Penetration Tester

USARemoteFull-time$196k–$236k2026-10-19 → 2026-11-10

Core

Lead the design, implementation, and expansion of a Continuous Adversarial Testing (CART) program for large application portfolios, including AI-assisted offensive security and autonomous tool oversight.

Role type

Senior IC lead penetration tester (adversarial testing & program strategy)

Builds

Continuous Adversarial Testing (CART) operating model, governance frameworks, and AI-assisted security testing workflows

Domain

Cybersecurity, offensive security, AI security, healthcare/finance regulated environments

Deliverable

production ML models

Required skills

Continuous security testing, attack simulation, breach and attack simulation, automated offensive security, governance establishment, finding triaging, vendor management, AI-enabled application assessment, DevSecOps, CI/CD security, OWASP Top 10, API Security Top 10, threat modeling, secure design, adversary emulation, exploit development

Preferred skills

AI-assisted security testing, autonomous security tool oversight, executive reporting, program documentation, stakeholder communication

Technologies

AI, API, CI/CD, Cloud, DevSecOps, LLM, OWASP, Security, WAF, Web, Windows