Senior Penetration Tester (REMOTE)

About the Role

The Senior Penetration Tester will serve as the Red Team technical lead for Offensive Security. They will lead red team threat emulation and advanced penetration testing services, defining testing strategies, executing complex assessments across diverse infrastructures, and serving as the primary technical authority for penetration testing. This role requires deep technical expertise, strategic vision, and leadership in guiding the team toward proactive risk management.

Responsibilities

• 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 for technical teams and stakeholders.
• Leads and executes end-to-end adversarial Red Team engagements, including scoping, 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, and collaboration with defensive teams.
• Leads and executes regular Threat Intelligence-led Purple Team Engagements with Blue Team, reporting to remediation teams and validating remediation after completion.
• Reports results of Purple Team Engagements to upper leadership.
• Leads retesting and validation efforts for critical vulnerabilities to ensure effectiveness of remediation measures.
• Conducts advanced assessments, provides strategic guidance, and delivers detailed feedback to improve security posture.
• May 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 to support long-term improvements in security strategy and architecture.
• May provide expertise for security projects throughout their lifecycle.
• Demonstrates mastery in penetration testing and red team operations, staying ahead of evolving threats and integrating new knowledge into team operations and training programs.
• Serves as the primary technical mentor for junior and mid-level penetration testers, providing in-depth training and fostering skill development.
• Produces high-level, strategic reports and documentation, including in-depth risk analyses and executive summaries.
• Communicates complex findings effectively to both technical teams and senior management.
• Oversees and manages ITSM workflow processes using tools like ServiceNow and Jira.
• Ensures documentation is comprehensive, accurate, and up-to-date.
• Manages time and resources effectively, balancing multiple projects and adapting to shifting priorities.
• Stays up-to-date with relevant laws, regulations, and compliance requirements impacting penetration testing and red teaming activities.
• Adheres to organizational codes of conduct and ensures all activities are conducted ethically and in compliance with legal and professional standards.
• Performs 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, 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 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 and tracking remediation efforts.
• 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.

Qualifications (Nice to Have)

• Competency-based certifications like OSCP, CRTO, eWPTX, OSEP, OSWE, OSED, OSCE3.
• Advanced Practical Penetration Testing and Red Team Certifications (e.g., OSEP, OSED, OSWE, OSCE3).

Physical & Mental Requirements

• Exposure to conditions that may be unpleasant to sight, touch, sound, or smell (occasional).
• Exposure to fumes, odors, dusts, mists, gases, biohazards, or other hazards (mechanical, electrical, burns, chemicals, radiation, sharp objects) (occasional).
• Exposure to noise, infectious waste, diseases, and conditions (occasional).
• Exposure to interruptions, shifting priorities, and stressful situations (frequent).
• Ability to follow tasks through to completion, understand complex ideas, remember multiple tasks over long periods, and work on concurrent tasks (continuous).
• Ability to read small print, hear sounds and speech patterns, and communicate instructions verbally (in-person or via phone/computer) with some background noise (continuous).
• Perform manual dexterity activities and grasping/handling (occasional).
• Ability to climb, kneel, crouch, or operate foot controls (occasional).
• Use a computer or other technology (continuous).
• Sit with the ability to vary physical position or activity (frequent).
• Maintain a safe working environment and use personal protective equipment (PPE) (occasional).
• Comply with applicable Code of Conduct, policies, procedures, and guidelines (continuous).
• Ability to provide assistance in the event of an emergency (occasional).
• Perform activities requiring standing or walking, with the ability to vary physical position or activity (occasional).
• Lift a maximum of 30 pounds unassisted (occasional).
• Use upper and lower extremities, engage in bending, stooping, reaching, pushing, or pulling (occasional).
• Work indoors under temperature-controlled and well-lit conditions (continuous).
• Encounter worksites with variable internal and external environmental conditions (occasional).
• Perform work involving physical efforts (e.g., transporting, moving, positioning, or ambulating patients) (occasional).