Director of Offensive Cyber Research

Twenty is seeking an exceptional Director of Offensive Cyber Research for an in-office position in its Arlington, VA office to lead and shape our entire offensive cyber research organization. We're looking for a visionary leader with 12+ years of distinguished experience spanning offensive cyber operations, threat research, software development, and organizational leadership, combined with a proven track record building and scaling high-performing technical teams in defense or intelligence environments. In this role, you'll oversee both our Forward Deployed Analyst teams embedded with government customers at operational sites and our Offensive Cyber Research Engineer teams developing next-generation offensive capabilities at our Arlington headquarters. You'll set the strategic direction for offensive cyber research, ensure our technologies meet real-world operational requirements, manage relationships with senior government stakeholders, and build a world-class organization that operates at the intersection of cutting-edge research and operational excellence. You'll leverage your deep operational pedigree—ideally from senior leadership positions in government/military Digital Network Exploitation Analysis (DNEA), Exploitation Analyst (EA) operations, or elite cyber units—combined with technical program management expertise to shape how Twenty defends 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 execute the strategic vision for Twenty's offensive cyber research organization, aligning technical capabilities with national security priorities and market opportunities

• Lead a distributed organization spanning Forward Deployed Analysts at government operational sites (Fort Meade, etc.) and Cyber Research Engineer teams in Arlington

• Serve as the executive-level technical authority on offensive cyber operations, advising Twenty's leadership team on capability development, technical risk, and strategic investments

• Drive the offensive cyber research roadmap, balancing near-term operational requirements with long-term innovation objectives

• Establish organizational priorities, resource allocation strategies, and success metrics for offensive cyber programs

• Represent Twenty at the highest levels of government, industry, and academic communities as a thought leader in offensive cyber research

Organizational Leadership & Team Building

• Build, lead, and scale a world-class offensive cyber research organization encompassing 20+ personnel across multiple disciplines and locations

• Recruit, develop, and retain top-tier talent including Analysts and Research Engineers (Associate through Principal levels), and technical program managers

• Foster a culture of operational excellence, technical innovation, continuous learning, and mission focus

• Establish clear career progression paths, professional development programs, and mentorship structures

• Create organizational structures and processes that enable seamless collaboration between forward-deployed teams and engineering teams

• Develop and manage operational budgets, headcount planning, and resource forecasting for the offensive cyber organization

• Conduct performance management, establish compensation strategies, and build retention programs for critical personnel

Customer & Stakeholder Management

• Own and manage strategic relationships with senior government officials, military leaders, and intelligence community stakeholders across multiple agencies and organizations

• Lead executive-level engagements including program reviews, capability demonstrations, and strategic planning sessions with government customers

• Translate operational requirements from government stakeholders into technical programs and development priorities

• Ensure Forward Deployed Analysts maintain operational credibility and deliver exceptional value at customer sites

• Drive contract growth, identify new business opportunities, and support proposal development for offensive cyber capabilities

• Navigate complex government acquisition processes, requirements development, and program execution frameworks

• Represent Twenty in industry forums, government advisory boards, and standards organizations

Technical Program Leadership

• Oversee the development of advanced offensive cyber capabilities including attack path frameworks, adversary emulation systems, and AI-powered automation tools

• Ensure offensive cyber technologies integrate seamlessly with Twenty's graph database platforms and electromagnetic domain capabilities

• Drive technical excellence across the organization while balancing innovation with operational readiness and delivery commitments

• Establish technical standards, development methodologies, and quality assurance processes for offensive cyber tool development

• Lead technical risk assessment and mitigation strategies for complex offensive cyber programs

• Ensure proper security practices, operational security (OPSEC), and compliance with government regulations across all offensive activities

Operational Excellence & Integration

• Ensure Forward Deployed Analysts effectively bridge the gap between operational requirements and engineering capabilities

• Establish feedback mechanisms that translate operator insights into engineering priorities and product improvements

• Create operational processes that enable rapid iteration and deployment of new offensive capabilities to government customers

• Oversee the integration of research innovations into operational workflows and customer missions

• Maintain awareness of evolving threat landscapes, adversary TTPs, and operational challenges facing government cyber operators

• Drive continuous improvement in how Twenty's offensive cyber capabilities support real-world missions

Cross-Functional Collaboration

• Partner with Twenty's product, engineering, and business development organizations to ensure offensive cyber capabilities align with company strategy

• Collaborate with backend, frontend, data engineering, and infrastructure teams to integrate offensive capabilities into Twenty's platform

• Work with legal, compliance, and security teams to ensure offensive cyber activities adhere to appropriate legal and ethical frameworks

• Coordinate with marketing and communications teams on thought leadership, recruiting, and brand building in the offensive cyber community

Qualifications

Experience & Expertise

• 12+ years of progressive experience in offensive cyber operations, threat research, and technical leadership with at least 5+ years in management or leadership roles

• Extensive operational cyber security experience with senior leadership roles in one or more domains:

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

  • Director or team lead roles for Exploitation Analyst (EA) operations conducting network exploitation and intelligence analysis

  • Leadership of enterprise-scale penetration testing/red team programs or elite cyber operations units

  • Senior positions in threat intelligence organizations tracking nation-state adversaries and APT groups

• Proven track record building and scaling technical organizations of 15+ personnel across multiple locations and disciplines

• Demonstrated success managing complex stakeholder relationships with senior government officials, military leaders, and intelligence community executives

• Deep technical expertise across offensive cyber operations, software development, data engineering, and system architecture

• Experience managing multi-million dollar budgets, contracts, and government programs

• Strong understanding of AI/ML technologies, graph databases, and large-scale data processing systems

Leadership & Management Skills

• Exceptional leadership presence with ability to inspire technical teams and influence executive-level decision-making

• Proven ability to recruit, develop, and retain world-class technical talent in competitive markets

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

• Demonstrated experience driving organizational change, establishing new teams, and scaling operations

• Strong business acumen with understanding of P&L management, contract vehicles, and government acquisition

• Experience conducting performance management, compensation planning, and organizational development

• Track record of fostering inclusive, collaborative cultures that drive innovation and operational excellence

Technical Knowledge

• Expert-level knowledge of offensive cyber operations, adversary TTPs, and red team methodologies

• Deep understanding of the MITRE ATT&CK framework and intelligence-driven adversary emulation

• Comprehensive knowledge of modern software development practices, architectures, and technologies

• Familiarity with graph databases, AI/ML systems, and data engineering for cyber operations

• Understanding of cloud platforms (AWS, Azure, GCP) and cloud-native security

• Knowledge of electromagnetic spectrum operations, IoT protocols, and multi-domain intelligence analysis

• Awareness of emerging technologies and their implications for offensive cyber capabilities

Education

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

• Executive education or leadership development programs a plus

Security Requirements

• Must possess TS/SCI security clearance with appropriate polygraph

• U.S. citizenship required

• Willingness to travel regularly between Arlington, VA and government operational sites (Fort Meade, etc.), with occasional travel to other locations

Distinguishing Qualifications

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

• Previous experience as a Director, Branch Chief, or equivalent leadership role in government or defense contractor environments

• Track record of winning and executing major government contracts or programs in the cyber domain

• Recognition as an industry thought leader through publications, keynote presentations, or advisory board positions

• Experience leading organizations through significant growth phases or organizational transformations

• Deep network of relationships across the Department of Defense, Intelligence Community, and interagency cyber communities

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

• Patents, innovations, or contributions that advanced the state of offensive cyber capabilities

• Experience bridging technical, operational, and business perspectives to drive organizational success

• Background leading both engineering R&D teams and operational support teams simultaneously

Additional Skills

• Experience with Agile methodologies, DevSecOps practices, and modern software development lifecycles

• Understanding of government contracting vehicles (GWACs, IDIQs, etc.) and proposal development processes

• Knowledge of export control regulations (ITAR, EAR) and their implications for offensive cyber technologies

• Familiarity with venture-backed or high-growth company environments and their unique challenges

• Experience with talent acquisition strategies, employer branding, and recruitment in competitive technical markets

• Understanding of modern HR practices, employee engagement strategies, and organizational development frameworks

• Strategic planning and OKR/goal-setting methodologies for technical organizations