Principal Offensive Cyber Research Engineer

Twenty is seeking a world-class Principal Offensive Cyber Research Engineer for an in-office position in its Arlington, VA office to serve as the preeminent technical authority and strategic leader for our offensive cyber capabilities. We're looking for someone with 8-12 years of distinguished expertise in offensive cyber operations, advanced research, and software development, combined with exceptional leadership experience shaping technical strategy, leading large-scale initiatives, and influencing organizational direction. In this role, you'll define the long-term technical vision for our offensive cyber research program, drive breakthrough innovations in adversary emulation and attack automation, establish company-wide standards for offensive tooling, and serve as the principal technical advisor to executive leadership and government customers on offensive cyber matters. You'll leverage your extensive operational pedigree—ideally including senior leadership roles in government/military Digital Network Exploitation Analysis (DNEA), Exploitation Analyst (EA) operations, or elite red team operations—to shape not just our technical capabilities but our strategic approach to defending democracies in the cyber domain.

About the Company

At Twenty, we're taking on one of the most critical challenges of our time: defending democracies in the digital age. We develop revolutionary technologies that operate at the intersection of cyber and electromagnetic domains, where the speed and complexity of operations exceeds human cognition. Our team doesn't just solve problems – we deliver game-changing outcomes that directly improve national security. We're pragmatic optimists who understand that while our mission of defending America and its allies is challenging, we can succeed.

Role Details

Strategic Leadership & Vision

• Define and drive the long-term technical vision and roadmap for Twenty's offensive cyber research and capabilities

• Serve as the principal technical advisor to executive leadership on offensive cyber strategy, capability development, and technical risk

• Lead strategic planning for offensive cyber programs, including resource allocation, technology investments, and partnership opportunities

• Represent Twenty as a technical authority in customer engagements, industry conferences, and government forums

• Influence company-wide technical decisions and architecture to ensure alignment with offensive cyber requirements

Advanced Research & Innovation

• Lead groundbreaking research into advanced adversary techniques, nation-state capabilities, and next-generation offensive cyber technologies

• Drive innovation in AI/ML-powered attack automation, autonomous adversary emulation, and machine-speed offensive operations

• Identify and pursue transformative research opportunities that position Twenty at the forefront of offensive cyber capabilities

• Establish research partnerships with government laboratories, academic institutions, and industry leaders

• Publish research findings in peer-reviewed venues and contribute thought leadership to the cyber security community

Technical Authority & Architecture

• Serve as the ultimate technical authority on offensive cyber operations, adversary TTPs, and red team methodologies across the organization

• Establish company-wide technical standards, frameworks, and best practices for offensive cyber tool development

• Lead architecture review boards and provide authoritative guidance on complex technical decisions

• Drive the evolution of Twenty's offensive cyber technology stack to maintain technical superiority

• Ensure technical excellence across all offensive cyber capabilities and maintain alignment with operational requirements

Organizational Leadership & Mentorship

• Lead and mentor the offensive cyber research team, including Staff and Senior engineers, establishing technical development plans and career growth paths

• Foster a culture of technical excellence, continuous learning, and innovation within the offensive cyber organization

• Conduct comprehensive technical reviews and provide expert guidance on complex research initiatives

• Recruit, interview, and assess top-tier offensive cyber talent to build world-class teams

• Collaborate across engineering, product, and operations organizations to ensure offensive capabilities integrate seamlessly with Twenty's broader mission

Customer & Stakeholder Engagement

• Lead technical engagements with senior government officials, military leaders, and intelligence community stakeholders

• Translate complex offensive cyber capabilities into strategic value propositions for executive-level audiences

• Drive requirements gathering and capability planning sessions with operational units and government customers

• Provide expert consultation on offensive cyber operations, threat landscapes, and adversary capabilities

• Build and maintain strategic relationships with key government partners and industry collaborators

Technical Contributions

• Architect and oversee development of advanced attack frameworks that operate autonomously at machine speed

• Lead development of sophisticated adversary emulation systems that replicate nation-state and APT behaviors across multiple operational domains

• Drive integration of graph databases, AI/ML systems, and large-scale data processing into offensive cyber workflows

• Establish data engineering standards for processing threat intelligence, operational data, and cyber observables at scale

Qualifications

Technical Skills & Experience

• 8-12 years of distinguished experience in offensive cyber operations, threat research, and advanced software development

• Expert-level operational cyber security experience with proven leadership in one or more domains:

  • Senior leadership roles in Digital Network Exploitation Analysis (DNEA) within U.S. Government military or intelligence organizations

  • Technical leadership of Exploitation Analyst (EA) teams conducting advanced network exploitation and intelligence operations

  • Leadership of elite penetration testing/red team operations at enterprise or national scale

  • Senior technical roles in threat intelligence organizations tracking nation-state and APT actors

• Extensive technical leadership experience including mentoring senior engineers, leading research organizations, and driving technical strategy

• Recognized expert in the MITRE ATT&CK framework and adversary behaviors with contributions to community understanding of advanced TTPs

• Demonstrated mastery of offensive cyber platforms and frameworks with track record of developing innovative tools that advance the state of the art

• Deep expertise integrating threat intelligence at strategic and tactical levels from diverse sources including government intelligence, commercial feeds, and original research

• Advanced knowledge of sophisticated attack techniques including rootkits, firmware exploitation, supply chain attacks, and advanced persistent mechanisms

• Expert-level software architecture and development capabilities with proven ability to design large-scale, distributed offensive cyber systems

• Mastery of graph-based analysis and AI/ML techniques applied to offensive cyber operations and threat emulation

• Comprehensive understanding of cybersecurity across all domains including network, application, cloud, mobile, IoT, and electromagnetic spectrum

• Extensive practical experience designing and executing complex offensive cyber campaigns that demonstrate deep understanding of OPSEC, tradecraft, and operational planning

Leadership & Communication Skills

• Exceptional leadership presence with proven ability to influence senior executives and government officials

• Outstanding communication skills with ability to articulate complex technical concepts to audiences ranging from engineers to policymakers

• Demonstrated track record driving organizational change and establishing technical direction

• Experience leading cross-functional initiatives involving engineering, product, operations, and business stakeholders

• Proven ability to represent organizations at the highest levels of government and industry

Education

• Master's degree or PhD in Computer Science, Cybersecurity, or related field preferred; Bachelor's degree with equivalent distinguished experience considered; or equivalent practical experience

Security Requirements

• Must possess TS/SCI security clearance with appropriate polygraph, or be eligible to obtain

Distinguishing Qualifications

• Senior leadership experience in prestigious government cyber operations units or intelligence organizations

• Track record of developing offensive cyber capabilities that achieved operational deployment and mission impact

• Recognition as a thought leader through publications, conference presentations, or contributions to offensive security research

• Advanced technical certifications demonstrating mastery (OSEE, GXPN, or equivalent government credentials)

• Patents or significant innovations in offensive cyber technologies or techniques

• Experience leading large-scale capability development programs involving multiple teams and organizations

• Deep background in malware development, vulnerability research, or exploit engineering with proven discoveries

• Experience with multi-INT fusion and intelligence analysis across cyber, SIGINT, ELINT, and other disciplines

• Advisory roles for government agencies, academic institutions, or industry standards bodies

• Contributions to open-source security communities that have achieved widespread adoption

Additional Skills

• Extensive experience with Agile and program management methodologies for research and development organizations

• Deep system architecture experience designing mission-critical security systems at scale

• Expert-level knowledge of cloud security across multiple providers (AWS, Azure, GCP) including sophisticated cloud-native attack techniques

• Comprehensive understanding of wireless security, IoT exploitation, 5G security, and electromagnetic spectrum operations

• Experience with defensive cyber operations, incident response, and threat hunting to understand defender perspectives

• Knowledge of government acquisition processes, requirements development, and program execution

• Understanding of international cyber law, rules of engagement, and policy considerations for offensive operations