Senior Penetration Tester (REMOTE)

Senior Level Penetration Tester

The Senior level Penetration Tester will serve as the Red Team technical lead for Offensive Security. They will be responsible for Red Team Engagements, Application Penetration Tests, and Purple Team Engagement activities.

The Senior Penetration Tester leads red team threat emulation and advanced penetration testing services for Trinity Health. This position is responsible for defining testing strategies, executing complex assessments across diverse infrastructures, and serving as the primary technical authority for penetration testing. The Senior Penetration Tester designs threat scenarios, provides strategic recommendations, and leads efforts to enhance the organization's overall security posture. This role requires deep technical expertise, strategic vision, and leadership in guiding the team toward proactive risk management.

• Leads penetration testing of network and application infrastructures, using both automated and manual testing techniques. Identifies vulnerabilities, evaluates potential risks, and documents findings thoroughly. Provides clear recommendations for remediation, ensuring reports meet professional standards and are suitable for technical teams and stakeholders.

• Leads and executes end-to-end adversarial Red Team engagements, including scoping and rules-of-engagement development, threat-informed attack planning, deployment and management of secure command-and-control infrastructure, execution of multi-stage attack paths, operational security, evidence collection, risk-based reporting, and collaboration with defensive teams to validate detection and response capabilities.

• Leads and executes regular Threat Intelligence-led Purple Team Engagements with Blue Team. Reports to teams responsible for remediation. Validates remediation after completion. Reports results of Purple Team Engagements to upper leadership.

• Leads retesting and validation efforts for critical vulnerabilities, ensuring the effectiveness of remediation measures and sustained security improvements. Conducts advanced assessments, provides strategic guidance, and delivers detailed feedback to improve security posture across the organization.

• May be consulted to assist in root cause analysis for security incidents, collaborating with cross-functional teams to identify systemic issues and potential security gaps. Provides strategic recommendations for corrective actions, supporting long-term improvements in security strategy and architecture.

• May be consulted to provide expertise for security projects throughout a project's lifecycle.

• Demonstrates mastery in penetration testing and red team operations, continuously seeking to expand knowledge of tools, techniques, and methodologies. Stays ahead of evolving threats and industry developments, integrating new knowledge into team operations and training programs.

• Serves as the primary technical mentor for junior and mid-level penetration testers (Penetration Tester I & II). Provides in-depth training, shares advanced knowledge, and promotes skill development. Drives team growth by leading technical workshops and fostering a collaborative learning environment.

• Produces high-level, strategic reports and documentation, including in-depth risk analyses, security recommendations, and executive summaries. Communicates complex findings effectively to both technical teams and senior management, ensuring clear understanding and actionable outcomes.

• Oversees and manages ITSM workflow processes using tools like ServiceNow and Jira. Ensures documentation is comprehensive, accurate, and up-to-date, optimizing task management and communication within the team and across the organization.

• Demonstrates the ability to effectively manage time and resources by setting clear priorities, balancing multiple projects, and adjusting plans as needed. Shows resilience and flexibility in adapting to new technologies, shifting organizational needs, and emerging security threats, ensuring continued productivity and alignment with strategic objectives.

• Keeps up-to-date with relevant laws, regulations, and compliance requirements that impact penetration testing and red teaming activities. Understands and adheres to organizational codes of conduct, ensuring all activities are conducted ethically and in compliance with legal and professional standards. Engages in regular training to stay informed about evolving regulations and best practices in the cybersecurity industry.

• Performs other duties as assigned.

Minimum Qualifications

• 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, with a demonstrated track record of leading complex assessments.
• Deep knowledge of Active Directory and Microsoft Entra ID architecture, authentication, authorization, privilege escalation paths, security controls, and cross-environment attack paths.
• Fluency in designing, building, and maintaining secure cloud-based command-and-control infrastructure.
• Expert-level experience developing and safely operating custom offensive capabilities for authorized adversary emulation, including controlled payloads, post-exploitation tooling, and C2 integrations for use in Red Team Engagements with Operational Security considerations.
• Advanced scripting and programming skills in languages like Python, C, or PowerShell, with experience in automating testing processes.
• Proficiency in using ITSM tools like ServiceNow and Jira for managing complex documentation, tracking advanced remediation efforts, and leading workflow optimization.
• Expertise in a wide range of penetration testing tools and custom exploitation techniques, capable of designing complex attack simulations and emulations.
• Extensive knowledge of compliance requirements, ethical best practices, and regulations impacting penetration testing.
• Actively pursues advanced certifications and continuously engages in professional development to remain at the forefront of industry trends.

Additional Qualifications (nice to have)

• Competency-based certifications like OSCP, CRTO, eWPTX, OSEP, OSWE, OSED, OSCE3.
• Advanced Practical Penetration Testing and Red Team Certifications. I.E. OSEP, OSED, OSWE, OSCE3 are highly desirable.

Physical & Mental Requirements & Working Conditions (General Summary)

• Exposure to conditions which may be considered unpleasant to sight, touch, sound, & / or smell. Occasional
• Exposure to fumes, odors, dusts, mists & gases, biohazards / hazards (mechanical, electrical, burns, chemicals, radiation, sharp objects, etc.). Occasional
• Exposure to noise, infectious waste, diseases & conditions. Occasional
• Exposure to interruptions, shifting priorities & stressful situations. Frequent
• Ability to follow tasks through to completion, understand & relate to complex ideas / concepts, remember multiple tasks & regimens over long periods of time & work on concurrent tasks / projects. Continuous
• Ability to read small print, hear sounds & voice / speech patterns, give / receive instructions & other verbal communications (in-person & / or over the phone / computer / device / equipment assigned) with some background noise. Continuous
• Perform manual dexterity activities & / or grasping / handling. Occasional
• Ability to climb, kneel, crouch & / or operate foot controls. Occasional
• Use a computer / other technology. Continuous
• Sit with the ability to vary / adjust physical position or activity. Frequent
• Maintain a safe working environment & use available personal protective equipment (PPE). Occasional
• Comply with applicable Code of Conduct, policies, procedures & guidelines. Continuous
• Ability to provide assistance in the event of an emergency. Occasional

Direct Healthcare Services:

• Perform activities that require standing / walking with the ability to vary / adjust physical position or activity. Occasional
• Lift a maximum of 30 pounds unassisted. Occasional
• Use upper & lower extremities, engage in bending / stooping / reaching & pushing / pulling. Occasional
• Work indoors (subject to travel requirements) under temperature-controlled & well-lit conditions. Continuous
• Encounter worksites (e.g., patient homes) or travel to worksites that may have variable internal & external environmental conditions. Occasional
• Perform work that involves physical efforts (e.g., transporting, moving, positioning & / or ambulating patients). Occasional

Indirect Healthcare / Support Services:

• Perform activities that require standing / walking with the ability to vary / adjust physical position or activity. Occasional
• Lift a maximum of 30 pounds unassisted. Occasional
• Experience of long periods of walking / standing / stooping / bending / pulling & / or pushing. Occasional
• Encounter a clinical / patient facing / hands on interactive work environment. Occasional
• Work indoors (subject to travel requirements) under temperature-controlled & well-lit conditions. Continuous
• Work outdoors with variable external environmental conditions. Occasional

Average Workday Activity: Occasional - O (1% - 33%), Frequent - F (34% - 66%), Continuous - C (67% - 100%)

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