Lead Penetration Tester

🔥 8 minutes ago

🇺🇸 United States – Remote

💵 $142.3k - $195.7k / year

⏰ Full Time

🟠 Senior

🔧 QA Engineer (Quality Assurance)

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Humana

WebsiteLinkedInAll Job Openings

10,000+ employees

Founded 1961

🏥 Healthcare

🛡️ Insurance

⚕️ Healthcare Insurance

Healthcare • Insurance • Healthcare Insurance

Humana is a healthcare company dedicated to making a positive impact on the health of individuals, communities, and the healthcare system as a whole. With a focus on putting health first, Humana serves a diverse range of populations, including seniors and the military, providing Medicare Advantage HMO, PPO, and PFFS plans. Humana is committed to fostering a culture of belonging and mutual respect, offering competitive and flexible benefits to ensure the financial security of its employees and their families. The company prides itself on creating an inclusive workplace where everyone has the opportunity to succeed.

📋 Description

• 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

• 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

• 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