Lead Penetration Tester, AI-Augmented Security (Remote)

Visa Hunt; United States; On-site; USD 142,000 - 196,000; Full time

Benefits offered by this job

Medical, dental and vision benefits

401(k) retirement savings plan

Paid time off & holidays

Training and conference budget

Job summary

Humana is seeking a technical leader for our penetration testing practice. This 100% remote role sits with the offensive-security team, aligned with Red Team, Breach & Attack Simulation, and Bug Bounty. Fridays are for research and development; HTB Pro Labs and training budgets are available.

You own the craft: testing methods, engagement quality, and AI-augmented tooling. Expect 7+ years in pen testing, deep app security across web, API, cloud, and AD, plus the ability to translate findings

Qualifications

• 7+ years in penetration testing, with ~2 years leading complex testing programs or technical workstreams
• Depth across modern attack surface: web apps, APIs, cloud, AD/Entra ID
• Hands-on testing of AI/LLM-powered applications (prompt injection, jailbreaks, adversarial techniques)
• Experience with agentic AI tooling or eagerness to adopt it
• Ability to translate deep technical findings into clear business risk for executives

Responsibilities

• Set and govern the team's testing methodology, playbooks, and evidence-quality bar; standardize complex assessments from scoping to reporting
• Lead the most complex penetration tests with full autonomy and mentor other testers
• Operate and mature agentic AI offensive tooling to improve coverage, triage, and evidence quality
• Translate technical findings into business risk for technical and executive stakeholders

Skills

Penetration testing

Lead testing programs

Agentic AI tooling

Testing methodology

Tools

Python scripting

PowerShell

Bash

Ruby

Job description

Humana is seeking a technical leader for our penetration testing practice. This 100% remote role sits with the offensive-security team, aligned with Red Team, Breach & Attack Simulation, and Bug Bounty. Fridays are for research and development; HTB Pro Labs and training budgets are available.

You own the craft: testing methods, engagement quality, and AI-augmented tooling. Expect 7+ years in pen testing, deep app security across web, API, cloud, and AD, plus the ability to translate findings