Jobs at Twenty

Leads federal government relations and advocacy strategy across Congress, the Executive Branch, the Department of Defense, and the Intelligence Community. Develops legislative, appropriations, and policy priorities; builds stakeholder relationships; monitors defense, technology, procurement, and cybersecurity developments; prepares executive policy materials; manages lobbying disclosures; and partners on lobbying, export-control, and procurement-integrity compliance.

Lead Twenty’s federal-focused communications strategy, media relations, executive communications, public affairs, and crisis communications. Translate cybersecurity, AI, defense, and national security topics into accurate narratives for policymakers, defense leaders, journalists, and the public. Write and edit press releases, op-eds, talking points, and thought leadership; prepare executives for media and congressional engagements; coordinate with Government Relations, Product, Sales, and Marketing; and manage reputational issues involving contracts, data security, and national security compliance.

Build, deploy, operate, and support software in a restricted government environment. Responsibilities include developing customer-specific features, data integrations, AI-backed capabilities, production debugging, observability, incident response, deployments, and root-cause analysis. The engineer will work directly with government users, coordinate with Arlington-based engineering teams, maintain runbooks, and operate systems in an air-gapped environment while holding an active TS/SCI clearance with CI polygraph.

Research Engineer investigates adversary techniques, develops offensive cybersecurity prototypes and reusable tools, analyzes cyber intelligence datasets, and supports attack-path analysis. The role collaborates with operators, analysts, researchers, and engineers to validate findings, document technical decisions, and deliver operationally useful security capabilities. Responsibilities include security tooling, automation, data enrichment, graph-based analysis, testing, code reviews, and communicating technical tradeoffs.

Own full-cycle, sourcing-heavy recruiting across G&A functions including Finance, Accounting, Legal, Talent, Operations, and selected Marketing roles. Build targeted pipelines, assess candidates, partner with hiring managers on role definition and interview processes, advise on leveling and market conditions, close passive candidates, maintain ATS accuracy, and improve recruiting workflows using data and AI.

Translate offensive cyber operations and intelligence workflows into technical requirements and operational products. Design and refine workflows using AI-powered graph database applications, integrate mission-relevant datasets, engage government customers, lead technical demonstrations, and shape new deployments. The role requires deep expertise in targeteering, DNEA, exploitation analysis, multi-domain intelligence, network analysis, operational planning, and cyber mission execution, while bridging operators, analysts, engineers, product teams, and senior government stakeholders.

Own and support the roadmap for agentic AI evaluation products. Define measures of agent performance, reliability, task success, and product quality; translate technical needs into requirements and workflows; partner with engineering and AI teams; operationalize evaluation processes; and use results to improve products and agent experiences.

Owns the end-to-end technical planning cycle across product and engineering teams, including intake, requirements readiness, estimation, delivery forecasting, status reporting, dependencies, risks, deployment milestones, and retrospectives. The role ensures teams and executives make explicit, accountable tradeoffs against customer and mission commitments. It requires strong software engineering depth, multi-team delivery planning experience, executive communication skills, and eligibility for a U.S. Government security clearance.

Own full-cycle, sourcing-heavy recruiting for Sales, Growth, business development, government relations, partnerships, and customer-facing leadership. Partner with leaders on role definition, candidate profiles, assessment plans, calibration, and closing. Build networks across cyber, defense, national security, and cleared talent communities; advise on market conditions, leveling, and timelines; maintain ATS accuracy; and improve recruiting workflows using AI.

Own the strategy, roadmap, prioritization, delivery, and iteration of data and platform capabilities supporting offensive cyber operations. Translate practitioner and engineering needs into reliable workflows, integrations, metrics, and product experiences. Partner with security researchers, engineers, and mission users while balancing usability, accuracy, auditability, speed, and legal considerations.

Own product discovery, roadmap, prioritization, requirements, delivery, and iteration for autonomous offensive-security and vulnerability-management capabilities. Partner with engineers, security practitioners, and mission users to translate complex cyber workflows into reliable product experiences. Define integrations, data needs, success metrics, and technical tradeoffs while balancing speed, usability, accuracy, auditability, and legal requirements.

Own product strategy and delivery for data and platform services supporting AI-enabled offensive cyber operations. Define roadmaps, requirements, workflows, integrations, data needs, reliability standards, and success metrics. Partner closely with engineers, security researchers, and mission users to build vulnerability-management and offensive-security capabilities. Translate complex cyber workflows into intuitive products while balancing speed, usability, accuracy, auditability, legal requirements, and security tradeoffs.

The role involves building financial models, managing budgeting and reporting, supporting fundraising, and overseeing operational systems. It seeks analytical and strategic problem solvers with finance experience.

Build and lead an engineering organization spanning cloud infrastructure, platform delivery, security engineering, site reliability, and government accreditation. Own software delivery into customer and restricted environments, production operations, incident response, vulnerability management, secure defaults, and accreditation programs. Hire and develop engineering leaders and teams, establish organizational structure, support product engineering, and communicate risks and tradeoffs to senior leadership.

Leads mission adoption and operational execution for offensive cyber capabilities across national security accounts. Translates company strategy into deployment plans, directs Deployment Managers and Forward Deployed Analysts, advises senior command leadership, shapes training and capability employment, translates mission needs into product direction, and owns account outcomes. Requires extensive senior cyber operations or intelligence leadership experience, active TS/SCI with FSP, U.S. citizenship, and regular onsite customer work.

Performs cyber operations and intelligence analysis, including DNEA, network analysis, persona development, and threat attribution. Serves as a subject-matter expert translating operational requirements into engineering specifications, validating AI-powered graph applications, gathering customer feedback, creating training materials, and leading technical demonstrations. Requires extensive U.S. Government cyber experience, active operational involvement, senior stakeholder engagement, and expertise across offensive and defensive missions.

Own frontend architecture for mission-critical React and TypeScript applications that visualize complex cyber operation data in real time. Lead UI technical direction, build interactive visualization systems, establish reusable component patterns, improve performance and reliability, and mentor engineers. Collaborate with product, design, backend, and operations teams to deliver secure, scalable capabilities for cloud and on-premises environments.

Build and operate production data integrations and ETL pipelines using AWS Glue, PySpark, Python, SQL, and ClickHouse. Responsibilities include designing schemas, integrating unfamiliar data sources, monitoring pipeline health, debugging incidents, improving observability, supporting restricted-environment deployments, and participating in on-call operations. The role collaborates with forward-deployed engineers and requires full-time onsite work in New York City, occasional travel to Arlington, and eligibility for a U.S. government security clearance.

Build and operate data integrations, ETL pipelines, schemas, monitoring, and production services in a restricted, air-gapped government environment. Develop extensions, deploy software across low- and high-side systems, monitor data quality and pipeline health, troubleshoot incidents, perform root-cause analysis, and create runbooks. Serve as the on-site engineering liaison between the customer and Arlington-based engineering and DevSecOps teams. The role requires independent judgment, customer-facing field engineering experience, and operational ownership.

Design and build high-throughput backend services for real-time operational data across cloud and on-premises environments. Lead architecture and technical execution for distributed, event-driven systems; define APIs; improve testing, code review, CI/CD, observability, and incident practices; troubleshoot production issues; mentor engineers; and partner with product, operations, and frontend teams to deliver secure, reliable capabilities.