Offensive Security Technical Lead in New York at Jobgether

This position is listed on behalf of a partner company, who manages all applications and next steps. Our partner is looking for an Offensive Security Technical Lead based in the United States.

The Offensive Security Technical Lead will own technical delivery across penetration testing and red-team workstreams supporting critical federal cybersecurity missions.
You will provide continuous assessment of external and internal cyber assets, helping uncover unknown exposures and validate vulnerabilities.
The role combines deep hands-on offensive security expertise with technical leadership across complex, concurrent assessments.
You will establish testing methodologies, govern operational risk, approve engagement plans, and ensure high-quality technical outcomes.
The position spans enterprise networks, applications, identity, cloud environments, exploit development, and adversary infrastructure.
You will work closely with technical teams, customers, and project leadership to translate attack paths and vulnerabilities into actionable mission and business risk.
This is a remote leadership opportunity with up to 25% travel across the Continental United States.

• Serve as the senior technical authority for penetration testing and red-team delivery across concurrent assessment engagements.
• Establish and continuously improve assessment methodologies, rules of engagement, technical review gates, evidence requirements, severity standards, reporting expectations, and reusable technical playbooks.
• Review and approve engagement plans, adversary scenarios, infrastructure designs, tooling exceptions, exploitation approaches, data-handling controls, and other high-risk technical activities.
• Govern technical risk and ensure testing remains aligned with customer objectives, authorization requirements, safety controls, staffing, methodology, and delivery commitments.
• Lead technical teams by providing guidance, allocating specialized expertise, mentoring offensive security professionals, conducting technical readiness reviews, and resolving complex cross-domain challenges.
• Provide hands-on support for advanced network, application, Active Directory and identity, cloud, exploit-development, adversary-infrastructure, and defense-evasion challenges.
• Own final technical quality and acceptance of assessment reports, attack-path narratives, severity decisions, remediation recommendations, customer briefings, and purple-team scenarios.
• Lead technical discussions with customers and communicate complex technical findings in terms of mission, operational, and business risk.
• Coordinate with project management on schedules, staffing, dependencies, and technical escalations without assuming administrative project-management responsibilities.
• Capture lessons learned, measure technical quality and repeatability, and continuously evolve offensive-security capabilities as customer environments, processes, and tools develop.

• U.S. citizenship required.
• No security clearance is required to begin employment; however, candidates must meet eligibility requirements for access to sensitive or classified information and be able to obtain a Department of Homeland Security Entrance on Duty (DHS EOD) authorization.
• 8+ years of progressively responsible offensive-security experience, including significant hands-on penetration testing and red-team or adversary-emulation work.
• 5+ years leading complex technical engagements, multiple concurrent assessments, or senior offensive-security teams.
• Expert-level ability to scope and safely govern testing across enterprise networks, applications and APIs, Windows/Active Directory and identity environments, Linux, AWS/Azure, external attack surfaces, and production systems.
• Demonstrated technical authority in rules of engagement, operational risk management, deconfliction, exploit validation, evidence quality, severity decisions, technical report acceptance, and customer out-briefing.
• Strong scripting, automation, and/or security tool-development capabilities, combined with sound judgment when evaluating high-risk technical approaches.
• At least one advanced hands-on offensive-security certification, such as OSEP/OSCE, OSWE, GXPN, GPEN, OSED/OSEE, CRTO/CRTL, or equivalent expert-level practical experience.
• Strong communication skills and the ability to translate complex technical attack paths into clear operational and mission risk for senior stakeholders.
• Ability to work effectively in customer-provided remote environments while following approved tools, rules of engagement, data-handling requirements, evidence controls, deconfliction procedures, and stop-work criteria.
• Willingness and ability to travel up to 25% within the Continental United States.

Preferred qualifications:

• 12+ years of experience across offensive security, security research, adversary emulation, or technical-assessment leadership.
• Experience leading CISA, DHS, federal high-value-asset, critical-infrastructure, ICS/OT, or similarly sensitive assessment programs.
• Experience developing or maturing offensive-security programs, quality metrics, training initiatives, or repeatable technical delivery standards.
• Advanced expertise in cloud security, identity, exploit development, malware or payload development, detection engineering, or purple-team operations.
• Experience briefing senior government leadership and translating sophisticated technical findings into mission and operational impact.

• Competitive annual salary range of approximately $105,100–$231,100, depending on geographic location, relevant experience, skills, education, certifications, and applicable contract requirements.
• Comprehensive healthcare and wellness benefits.
• Financial and retirement benefits designed to support employees and their families.
• Flexible time-off benefits supporting work-life balance.
• Continuing education, professional development, and learning resources.
• Career growth opportunities within complex federal cybersecurity and national-security missions.
• Flexible remote work environment.
• Regular exposure to advanced offensive-security challenges and high-impact government cyber programs.
• Full-time, regular employment.
• Up to 25% travel within the Continental United States.
• Opportunity to contribute to efforts focused on strengthening the security and resilience of critical national cyber infrastructure.