Full-time

AI Security Testing Lead

Posted by Insight Global • Chicago, IL, United States

📍 Chicago, IL 🕒 June 20, 2026

About the Role

Job Description
· Lead and execute AI security assessments of Copilot-like apps, LLM applications, RAG pipelines, and agent/tool integrations.

· Formalize and operationalize an AI testing methodology (scope → test plan → execution → reporting → retest) suitable for regulated enterprise use.

· Stand up and mature non-prod AI testing infrastructure and repeatable workflows (safe test data, access patterns, evidence capture, reusable harnesses).

· Enable existing pentesters via training, playbooks, reusable test packs, and quality review of findings/evidence.

· Drive governance and defensibility: human-in-the-loop decisions, safe testing constraints, reproducible evidence, and consistent severity rationale.

· Communicate outcomes to technical teams and leadership: themes, control gaps, remediation priorities, and validation results.

· Demonstrated hands-on experience assessing AI-enabled applications, including one or more of:
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