Jobgether
Jobgether

Offensive Security Technical Lead

engineeringfull-timeUS
SALARY
$105k – $231k/yr
WORK TYPE
remote
JOB TYPE
full-time
INDUSTRY
general
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About the role

Accountabilities

    • 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.
    • Requirements

      • 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.
        • Benefits

          • 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.
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