Twenty

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) 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.

Mission | On Site | Full Time | Active TS/SCI with Full Scope Polygraph OR Active TS/SCI with CI Polygraph

About the Role

Twenty builds AI-native software for cyber mission teams operating in complex intelligence environments.

We are looking for a Mission Deployment Lead to make Twenty’s products operationally useful for Intelligence Community users. This role is for someone who understands cyber operations, targeting, networking environments, and mission planning.

You will work directly with operators, analysts, mission owners, program staff, product managers, and engineers. Your job is to understand real workflows, drive adoption, surface friction, translate field feedback into product decisions, and make sure Twenty is solving problems that matter.

This role requires an active TS/SCI with CI Poly and regular onsite work at customer locations.

What You’ll Own

• Own mission adoption for IC users of Twenty’s products, moving teams from demo and pilot usage into recurring operational workflows.

• Map real mission workflows across planning, targeting, execution support, assessment, collaboration, and reporting to Twenty capabilities.

• Lead onboarding, hands-on training, working sessions, and enablement across the distinct workflows of operators and targeters based on your understanding of their unique needs and requirements.

• Build and adapt playbooks, quick-start guides, and repeatable workflow patterns based on what works in real mission environments.

• Maintain the field operating picture for each deployment: users, stakeholders, workflows, blockers, adoption signals, product requests, risks, next actions, and value stories.

• Turn user feedback into clear product requirements, bug reports, workflow improvements, and engineering context.

• Partner with product and engineering to test workflows, triage issues, validate fixes, and keep roadmap decisions grounded in mission reality.

• Support demos, pilots, and expansion into adjacent teams where Twenty is already creating mission value. This is a mission adoption role, not a quota-carrying sales role.

Preferred Qualifications

• 5+ years prior experience as a cyber operator, targeter, mission planner, or intelligence professional supporting real-world operational workflows in the Intelligence Community.

• Direct experience with complex cyber operations, while supporting operators, targeters, mission leads, technical directors, and program stakeholders.

• Working understanding of cyber mission workflows and how they intersect with intelligence production, planning, tasking, execution support, and assessment.

• Ability to learn complex software quickly and explain it clearly to technical and non-technical users.

• Experience with graph-based tools, link-analysis platforms, analytic platforms, BI tools, mission systems, or workflow software.

• Strong written communication. You can turn ambiguous field input into concise requirements, action items, status updates, and executive-ready summaries.

• Bias toward ownership in ambiguous environments.

Role Details

Workplace: On Site and In Office

Employment: Full Time

Department: Mission

Clearance: Active TS/SCI with CI Poly

Travel: Occasional travel for customer engagements, training, and mission support

Benefits
What's on the table:

• Health. Medical, dental, and vision plan options. Life / AD&D, disability coverage options.

• Family. Paid parental leave for eligible full-time employees. 12 weeks for birthing parents, 4 for non-birthing parents, 6 weeks for adoptive, foster, or intended parents through surrogacy.

• Vacation. Paid holidays and flexible PTO. Take what you need.

• Retirement. 401(k) with pre-tax and Roth options. HSA/FSA options, dependent care FSA.

Benefits vary by location, role, and eligibility. Full plan details provided during the interview and offer process.

Due to U.S. government contract and security requirements, this role is limited to U.S. citizens. Some positions may also require eligibility to obtain and maintain a U.S. Government security clearance. Any active 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, consistent with applicable law.

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