Director of Offensive Cyber Research

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 the cyber and electromagnetic domains, where the speed of operations exceeds human sensing and complexity transcends conventional boundaries. Our team doesn't just solve problems – we deliver game-changing outcomes that directly impact national security. We're pragmatic optimists who understand that while our mission of protecting America and its allies is challenging, success is possible.

Role Summary

You will lead and shape Twenty’s offensive cyber research organization—setting strategy, building a world-class team, and ensuring our capabilities meet real operational needs. You’ll oversee both forward-deployed analysts working alongside government mission teams and research engineers developing next-generation offensive capabilities from our Arlington headquarters. You’ll partner closely with product, engineering, and business leaders, and you’ll represent Twenty with senior government stakeholders. This role sits at the intersection of cutting-edge research, disciplined delivery, and mission outcomes.

Who You Are

• You care deeply about defending democracies and delivering technology that matters in real operations.

• You lead with high standards and high support—direct feedback, clear expectations, and strong follow-through.

• You can set a long-term vision without losing the near-term: you prioritize, sequence, and ship.

• You translate between operators, engineers, and executives—building trust across different incentives and languages.

• You’re calm under pressure and decisive with incomplete information.

• You run organizations like systems: metrics, incentives, hiring, and process are tools to increase mission impact.

• You bring strong judgment around security, OPSEC, and responsible execution in sensitive environments.

What You’ll Do

• Set and execute the strategy and roadmap for Twenty’s offensive cyber research capabilities.

• Lead a distributed organization spanning forward-deployed analysts and Arlington-based research engineering teams.

• Serve as the executive technical authority for offensive cyber operations and capability development decisions.

• Build and scale a high-performing org (20+), including hiring, mentoring, performance management, and retention.

• Ensure operator feedback loops consistently translate into engineering priorities and product improvements.

• Own senior government relationships, including reviews, demonstrations, and strategic planning engagements.

• Balance innovation with operational readiness—raising engineering excellence while meeting delivery commitments.

• Establish technical standards, development methodologies, and quality practices for offensive tool development.

• Manage budgets, headcount planning, and resource forecasting across offensive cyber programs.

• Partner cross-functionally with product, engineering, security, legal/compliance, and business development.

Must Have

• You have 12+ years of experience spanning offensive cyber operations, threat research, and technical leadership.

• You have 5+ years leading teams, including hiring, performance management, and org design.

• You have built and scaled technical teams (15+ people) across multiple locations and disciplines.

• You have senior operational leadership experience in at least one of: DNEA, exploitation analysis, elite cyber units, or enterprise-scale red team programs in defense/intelligence environments.

• You have a track record delivering complex, multi-stakeholder programs from requirements through operational outcomes.

• You have experience managing senior government stakeholders and navigating government program execution dynamics.

• You have owned budgets/contracts and driven resourcing decisions for mission-critical technical programs.

• You are a U.S. citizen and currently hold an active TS/SCI security clearance with an appropriate polygraph.

• You are willing to travel regularly between our HQ in Arlington, VA and government operational sites (Fort Meade, etc.), with occasional travel to other locations

Nice To Have

• You have led both R&D engineering teams and operational support teams simultaneously.

• You have experience with AI-enabled automation, graph-based cyber analytics, or large-scale cyber data systems.

• You have familiarity with cloud-native security and modern DevSecOps practices in sensitive programs.

• You’re recognized externally through publications, keynotes, standards work, or advisory participation.

• You hold advanced certifications (e.g., OSEE, GXPN, CISSP or equivalent government credentials).

• You’ve operated in high-growth or venture-backed environments and can scale teams and process quickly.

Tech Environment (You Might Work With)

• Offensive capability R&D: attack path frameworks, adversary emulation, and automation tooling

• Graph-based platforms and large-scale data processing for cyber operations

• Secure software delivery, DevSecOps pipelines, and quality systems for operational tooling

• Cloud platforms (AWS, Azure, GCP) and cloud-native security patterns

• Intelligence-driven tradecraft and frameworks (e.g., MITRE ATT&CK)

Security / Work Environment

This role requires an active TS/SCI with an appropriate polygraph. This role may involve work in a controlled environment.

If this role sounds like you, apply and share with us your interest.

Some positions may require eligibility to obtain a U.S. Government security clearance. Any clearance requirement will be listed in the role description.

Twenty is an equal opportunity employer. We consider all qualified applicants without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, age, veteran status, disability, or any other protected status.

If you need a reasonable accommodation during the hiring process, let us know and we will work with you.