Director of Offensive Cyber Research

Twenty-posted 2 months ago

Full-time • Senior

Washington, DC

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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.

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 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
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
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
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
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
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

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

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
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

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