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Join a 100% remote, highly specialized offensive security team where collaboration and continuous learning drive our success. We foster a supportive environment focused on collective growth and technical excellence, where every team member contributes to our shared mission. You will have access to Hack The Box Pro Labs, all HTB role-based training paths and certifications, discretionary certification funding, and conference/training budgets. These resources will enable you to continuously advance your expertise while working on industry-leading application security challenges. You will be part of Cyber Threat Simulation (CTS), collaborating with Red Team, Breach and Attack Simulation, and Bug Bounty professionals, highly specialized experts who identify vulnerabilities so the business can address them proactively. Fridays are dedicated to research and development, allowing the team to pursue training in emerging offensive security technologies, tools, large language models (LLMs), artificial intelligence, and other relevant topics.
The Senior Penetration Tester enables secure and compliant business operations by performing application security-focused penetration tests. This role helps maintain PCI-DSS compliance and supports the team's success by:
? Contributing technical expertise during the consulting rotation and occasionally during "lunch & learns."
? Identifying and documenting novel vulnerabilities in web applications, APIs, thick clients, Cloud, and AI/LLM/ML-powered applications.
? Leading moderate to complex penetration tests with autonomy and making recommendations to leadership based on advanced knowledge and experience.
? Leading closing meetings with business stakeholders such as application owners, security teams, information security offices, and other internal customers.
The position focuses on scoping, planning, executing, documenting, and sharing the findings of penetration tests and providing valuable input that influences the strategy and direction of the penetration testing functional area within the enterprise's offensive security program by collaborating with the Associate Director, Penetration Testing.
Mission & Impact
Conduct comprehensive security assessments to identify vulnerabilities across Humana's technology infrastructure and translate technical findings into actionable business risk recommendations. You will leverage deep offensive security expertise to design and execute penetration tests, develop custom testing methodologies, and manage multiple concurrent security assessments.
Your week involves reviewing new applications for security assessment opportunities, executing advanced penetration testing techniques across web applications and cloud environments, developing detailed remediation guidance, and presenting findings to both technical and executive stakeholders.
Why it matters: Every assessment you complete identifies real-world vulnerabilities before attackers do, helping Development, Infrastructure, and Security teams strengthen our overall defensive capabilities.
You'll do well in this role if you are skilled in advanced exploitation techniques, enjoy translating complex technical vulnerabilities into clear business risk, and prefer delivering evidence-based security recommendations over theoretical discussions.
Key Responsibilities
Security Assessment Delivery: Design and execute comprehensive penetration tests across web applications, network infrastructure, cloud environments, and mobile platforms using industry-standard tools and custom methodologies. Develop targeted test cases for specific technologies and environments not covered by standard approaches. Ensure assessments meet service level agreements, such as completing standard web application assessments within established timeframes, while operating with minimal guidance on complex testing scenarios.
Technical Expertise & Innovation: Maintain proficiency with current testing tools, exploit techniques, and emerging attack vectors with considerable autonomy. Research and integrate new testing methodologies and develop custom tools when commercial solutions are insufficient. Apply advanced technical knowledge to overcome complex security controls and identify sophisticated attack paths.
Stakeholder Communication & Documentation: Draft comprehensive technical reports with clear risk assessments and actionable remediation guidance for technical and executive audiences. Present findings to development teams, infrastructure groups, and business stakeholders. Use independent judgment to prioritize findings based on business impact, exploitability, and organizational risk tolerance.
Strategic Collaboration: Occasionally collaborate with architecture and engineering teams as a consulted stakeholder, and deconflict alerts as requested by incident response and threat hunting teams. Make recommendations regarding security testing approaches based on offensive security expertise and best industry practices.
Continuous Improvement: Propose enhancements to testing methodologies, identify gaps in organizational security controls, and suggest new assessment approaches to address emerging threats. Your technical insights and proactive recommendations will significantly influence CTS testing strategy and organizational security improvements.
Use your skills to make an impact
Minimum Qualifications
Minimum 5 years of experience in penetration testing, ethical hacking, or offensive security operations
Advanced proficiency in scripting languages such as Python, PowerShell, Bash, or Ruby for automation and custom tool development
Excellent communication skills with experience in presenting technical findings to both technical and executive stakeholders
Knowledge of regulatory compliance frameworks, particularly PCI DSS penetration testing requirements and methodologies
Experience with major Cloud Service Providers, including AWS, Azure, and GCP-security testing
Demonstrated ability to work autonomously on complex technical security assessments
Experience with enterprise security testing across network infrastructure, mobile and web applications, and cloud environments
Proficiency with industry-standard tools, including Burp Suite, Metasploit, Nmap, BloodHound, and custom exploitation frameworks
Strong understanding of network protocols, web application architectures, and enterprise security technologies
Relevant industry certifications, including but not limited to: OSCP, OSWE, CPTS, CBBH, or equivalent advanced credentials
Preferred Qualifications
7+ years of experience in any of the following areas:
Advanced penetration testing or red team operations
Application Security-focused research and exploit development
Expertise in Mobile application security testing (iOS/Android)
Experience performing Cloud (AWS, Azure, or GCP), Microsoft Active Directory, and Entra ID-focused security assessments
Published research, blog posts, or speaking engagements at industry conferences such as DEF CON, BSIDES, Black Hat, or regional security conferences
CWEE, OSCE3
Familiarity with AI/ML security testing, including LLM-powered applications, prompt injection attacks, and AI model security assessments
Experience with security automation, CI/CD pipeline security testing, and DevSecOps practices
Travel: While this is a remote position, occasional travel to Humana's offices for training or meetings may be required.
Scheduled Weekly Hours
40
Pay Range
The compensation range below reflects a good faith estimate of starting base pay for full time (40 hours per week) employment at the time of posting. The pay range may be higher or lower based on geographic location and individual pay will vary based on demonstrated job related skills, knowledge, experience, edu
