Lead Penetration Tester

Humana

Lead penetration testing for Humana's cybersecurity efforts. Focus on AI-augmented methodologies in a fully remote role.

Posted 7/31/2026full-timeRemote • 🇺🇸 United StatesSenior💰 $142,300 - $195,700 per yearWebsite

Core Competencies

Role fit

Core Competencies

Use this summary to align your resume positioning with the role.

Demonstrates extensive expertise in penetration testing and offensive security operations, with a focus on leading complex assessments of web applications, APIs, and AI systems. Proficient in translating technical findings into business risks for stakeholders while ensuring compliance with standards like PCI-DSS.

Highest-signal resume keywords

Penetration TestingAI/LLM Application SecurityCloud Security (AWS/Azure/GCP)Adversarial Assessment TechniquesCompliance Testing (PCI-DSS)

ATS Keywords

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Applicant Tracking System Keywords

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Hard Skills

Penetration TestingEthical HackingOffensive Security OperationsWeb Application SecurityAPI SecurityCloud SecurityActive Directory SecurityAdversarial TechniquesPrompt InjectionJailbreaks

Soft Skills

CommunicationLeadershipRisk Translation

Tools & Technologies

Agentic AI Tooling

Certifications & Qualifications

OSCPOSWEOSCE3CPTSCWEE

Industry Keywords

Compliance TestingTesting MethodologyEvidence QualityEmerging ThreatsOrganizational Controls

Tech Stack

Tools & technologies

AWSAzureCloudGoogle Cloud Platform

About the role

Key responsibilities & impact

Set and govern the team's testing methodology, playbooks, and evidence-quality bar
Lead the most complex penetration tests (web apps, APIs, cloud, AD/Entra ID, AI/LLM applications) with full autonomy
Operate and mature the team's agentic AI offensive tooling
Lead adversarial assessments of AI/LLM applications, prompt injection (direct/indirect), jailbreaks, and adversarial techniques
Identify gaps in testing coverage and organizational controls, propose new assessment approaches for emerging threats
Translate technical findings into business risk for technical and executive stakeholders
Support PCI-DSS and other compliance-driven testing obligations

Requirements

What you’ll need

7+ years in penetration testing, ethical hacking, or offensive security operations, with ~2 years leading complex testing programs or technical workstreams
Depth across the modern attack surface, web apps, APIs, cloud (AWS/Azure/GCP), and Active Directory / Entra ID, with a track record leading the most complex assessments autonomously
Hands-on testing of AI/LLM-powered applications (prompt injection, jailbreaks, adversarial techniques), or demonstrated ability to secure emerging AI systems
Experience operating or eagerness to use agentic AI tooling
Ability to translate deep technical findings into clear business risk for executives
Certifications are a plus, e.g. OSCP, OSWE, OSCE3, CPTS, CWEE, or equivalent advanced credentials

Benefits

Comp & perks

medical, dental and vision benefits
401(k) retirement savings plan
time off (including paid time off, company and personal holidays, paid parental and caregiver leave)
short-term and long-term disability
life insurance and many other opportunities