Senior Penetration Tester

Job not on LinkedIn

🕒 August 4

🚗 Michigan – Remote

🚗 Michigan – Remote

⏰ Full Time

🟠 Senior

🔧 QA Engineer (Quality Assurance)

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Trinity Health

WebsiteLinkedInAll Job Openings

10,000+ employees

🏥 Healthcare

📚 Education

🤝 Non-profit

Healthcare • Education • Non-profit

Trinity Health is a Christian K-12 educational institution located in Wichita, Kansas, dedicated to providing a Christ-centered education that nurtures spiritual growth and academic excellence. The academy emphasizes the importance of faith in students' lives, integrating spiritual development with rigorous academic programs and a broad array of extracurricular activities, including athletics and fine arts. Trinity Health fosters a supportive community where teachers and families collaborate to help students develop a personal relationship with Jesus Christ and excel in their studies.

📋 Description

• Lead penetration testing of network and application infrastructures using automated and manual techniques • Identify vulnerabilities, evaluate risks, document findings, and provide remediation recommendations • Lead end-to-end adversarial Red Team engagements, including scoping, rules of engagement, attack planning, C2 infrastructure, multi-stage attack paths, operational security, evidence collection, and reporting • Lead Threat Intelligence-led Purple Team Engagements with Blue Team and validate detection, response, and remediation • Lead retesting and validation of critical vulnerabilities • Assist with root cause analysis for security incidents and recommend corrective actions • Provide security expertise throughout project lifecycles • Expand offensive security knowledge and integrate new tools, techniques, and methodologies into team operations and training • Mentor junior and mid-level penetration testers and lead technical workshops • Produce strategic reports, risk analyses, security recommendations, and executive summaries • Oversee ITSM workflows using ServiceNow and Jira • Manage priorities, multiple projects, resources, and changing security needs • Maintain awareness of laws, regulations, compliance requirements, and ethical standards • Perform other duties as assigned

🎯 Requirements

• Bachelor’s degree in Information Security, Computer Science, or a related field; equivalent experience considered in lieu of degree • 6–8+ years of experience in penetration testing, red teaming, or a related field • Demonstrated track record leading complex assessments • Deep knowledge of Active Directory and Microsoft Entra ID architecture, authentication, authorization, privilege escalation, security controls, and cross-environment attack paths • Ability to design, build, and maintain secure cloud-based command-and-control infrastructure • Expert experience developing and safely operating custom offensive capabilities for authorized adversary emulation • Experience with controlled payloads, post-exploitation tooling, C2 integrations, and operational security • Advanced scripting and programming skills in Python, C, or PowerShell • Experience automating testing processes • Proficiency with ServiceNow and Jira for documentation, remediation tracking, and workflow optimization • Expertise in penetration testing tools and custom exploitation techniques • Extensive knowledge of compliance requirements, ethical best practices, and regulations affecting penetration testing • Active pursuit of advanced certifications and ongoing professional development • Preferred certifications include OSCP, CRTO, eWPTX, OSEP, OSWE, OSED, and OSCE3

🏖️ Benefits

• Professional development and training opportunities • Support for pursuing advanced certifications • Mentoring and technical workshop participation • Equal employment opportunity