Twenty is a cyber warfare startup that builds AI-enabled, end-to-end offensive cyber systems for the U.S. military and the Intelligence Community.
ABOUT THE COMPANY America is under sustained cyber attack. Our adversaries infiltrate our networks, steal our IP, and degrade the digital infrastructure that modern life runs on. They’ve learned—correctly—that those attacks rarely produce consequences. Twenty was founded to change that, by making our adversaries think twice before they attack us. Our vision is American and allied primacy in cyberspace—a future where they cannot contest us, deterrence is assured, and the free world remains secure. Founded in 2024, Twenty Technologies (www.twenty.io http://www.twenty.io) industrializes offensive cyber operations for the U.S. and its allies. Headquartered in Arlington, Virginia, Twenty has raised $168M from Khosla Ventures, Accel, Caffeinated Capital, Friends & Family Capital, Point72 Ventures, General Catalyst, and In-Q-Tel. Role Overview Twenty is seeking a Offensive Solutions Architect to bridge elite Title 50 cyber tradecraft with Twenty’s AI‑powered cyber operations products. This role is for a senior operator or targeteer whose credibility and operational excellence already make them a go‑to voice for shaping missions – and who now wants to scale that impact by 100× through software. You’ve spent years in offensive cyber operations and intelligence analysis. You’re the person key stakeholders seek out before they do hard things. You understand how missions actually run across DNEA/EA, multi‑domain intelligence, and complex targeting problems, and you care most about more/better/faster operational impact. At Twenty, you'll be equally comfortable engaging highly technical cyber operations personnel, program personnel of varying seniority, and senior intelligence officials. Your impact will be magnified by our world-class engineering team as you ensure that our AI-powered graph database applications meet the complex demands of modern cyber operations. --- What You’ll Do Subject Matter Expertise & Requirements Translation - Maintain operational proficiency and credibility through regular engagement with live cyber operations and intelligence production (within appropriate constraints). - Serve as a primary SME for cyber operations and intelligence analysis, translating complex operational workflows into clear, prioritized technical requirements for Twenty’s product and engineering teams. - Validate that our AI‑powered graph database applications accurately represent and enhance offensive and defensive cyber operations, including DNEA / EA tradecraft. - Lead structured requirements‑gathering sessions with government customers and convert operational needs into actionable, testable development work. Growth Engineering & Workflow Design - Go beyond demos: design, build, and refine operational workflows in Twenty’s products for new and existing IC user groups. - Work directly with cyber operators and analysts to gather feedback on user interfaces, graph models, and workflows, then iterate quickly with Forward Deployed Analysts and core engineering. - Identify relevant datasets and signals through deep engagement with customer problems, and partner with Forward Deployed Analysts to integrate them into stable, extensible pipelines. - Present mission workflows, results, and next‑step proposals to audiences ranging from operators to senior executives. - Scope new deployments and use cases across additional IC elements, helping Twenty expand from initial adopters to broader mission footprints. Customer Engagement & Strategic Leadership - Represent Twenty in customer engagements, using your operational credibility to build trust and long‑term partnerships. - Lead high‑impact technical demonstrations that show how our AI and graph capabilities materially improve mission outcomes (more/better/faster operations across more targets). - Collaborate with government stakeholders to surface emerging operational requirements, capability gaps, and opportunities for new product directions. - Act as the connective tissue between operators, leadership, and Twenty’s internal teams so we always build for real‑world mission impact, not slideware. --- Qualifications Operational Experience & Expertise - 10+ years of professional experience in cyber operations and intelligence analysis within U.S. Government military or intelligence organizations. - Deep expertise in Targeteering, Digital Network Exploitation and Analysis (DNEA) and/or Exploitation Analyst (EA) methodologies and tools. - Strong understanding of both offensive and defensive cyber mission sets and how they intersect with other domains. - Extensive experience with multi‑domain intelligence analysis (e.g., correlating CYBER, SIGINT, GEOINT, HUMINT) in support of real operations. - Demonstrated expertise in network analysis, persona development, and threat actor attribution. - Strong background in operational planning and mission execution in cyber environments, including shaping and assessing effects. Technical Skills & Knowledge - Advanced understanding of network protocols, exploitation techniques, and cyber attack methodologies. - Experience using graph‑based analysis tools and methodologies for intelligence analysis and targeting. - Familiarity with AI/ML applications in cyber operations or intelligence analysis, and interest in pushing these further in production systems. - Understanding of cloud platforms and their security implications for government/IC environments. - Familiarity with IoT protocols, Wi‑Fi exploitation, and electromagnetic spectrum operations. - Experience with data visualization tools and techniques for complex intelligence products and decision briefs. Leadership & Communication - Proven ability to translate complex operational and technical concepts for diverse audiences, including senior government officials. - Experience mentoring analysts or leading operational teams, with examples of raising the bar f