Remote Lead Pentest Engineer – AI-Driven Security Craft

Humana Inc; Madison (WI); On-site; USD 142,000 - 196,000; Full time

Benefits offered by this job

Remote work

Bonus incentive plan

Certification funding

Job summary

Humana Inc. seeks a seasoned penetration testing leader to own the testing craft across web, API, cloud, and AI‑powered systems.

You’ll set methods, playbooks, and evidence standards, lead the most complex engagements, and drive AI‑augmented testing adoption within a remote team. You’ll translate technical findings into business risk for leadership, mentor testers (not managers), and influence strategy while ensuring PCI‑DSS and other obligations are met.

Qualifications

• 7+ years in penetration testing, ethical hacking, or offensive security operations.
• Depth across the modern attack surface: web apps, APIs, cloud, AD/Entra ID, with autonomous leadership of complex assessments.
• Experience testing AI/LLM systems (prompt injection, adversarial techniques) or ability to secure AI systems.
• Experience operating agentic AI tooling or readiness to adopt it and lead a team's move toward it.
• You set/testing standard; translate technical results into business risk for executives.
• Certifications are a plus (OSCP/OSWE/CPTS/CWEE) not a gate.

Responsibilities

• Set and govern the team's testing methodology, playbooks, and evidence‑quality bar; standardize how complex assessments are scoped, executed, and reported.
• Lead the most complex penetration tests with full autonomy, mentoring other testers on technique while not managing them.
• Operate and mature the team's agentic AI offensive tooling to improve coverage, triage, and evidence quality; evaluate AI-assisted findings for risk and accuracy.
• Test AI systems: lead adversarial assessments of AI/LLM applications mapped to OWASP Top 10 for LLM; MITRE ATLAS; NIST AI RMF.
• Influence the functional strategy, identify coverage gaps, propose new assessment approaches, and shape practice investments.
• Translate findings into business risk for executives; lead closing meetings with owners and security teams.
• Support PCI‑DSS and other compliance‑driven testing obligations at program standard.

Skills

Penetration testing leadership

AI/LLM testing

Testing methodology

Adversarial testing

Mentoring testers (not managers)

Education

OSCP/OSWE/CPTS

Tools

Python scripting

PowerShell/Bash

Job description

Humana Inc. seeks a seasoned penetration testing leader to own the testing craft across web, API, cloud, and AI‑powered systems.

You’ll set methods, playbooks, and evidence standards, lead the most complex engagements, and drive AI‑augmented testing adoption within a remote team. You’ll translate technical findings into business risk for leadership, mentor testers (not managers), and influence strategy while ensuring PCI‑DSS and other obligations are met.