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 CI Polygraph
Role Summary
Twenty builds AI-native software for offensive cyber teams operating in complex mission environments. We are looking for a Command Mission Operations Lead to own how Twenty’s capabilities and delivery team integrate with current state and future state cyber weapons systems to maximize cyber force generation. You are a cyber warfare professional whose judgement and reputation are widely respected in the community. You will be the trusted face of Twenty with mission and task force leadership who is able to provide both tactical and strategic advice on force and capability employment against persistent nation state cyber threats.
This is a mission adoption and operational leadership role, not a quota-based sales role.
This role is for someone who has directly commanded cyber operations or advised command or JFHQ-level senior leadership on force employment, and is credible with operators and analysts at the tactical level.
The people who do this well have usually been an O-5/O-6, a Warrant Officer, or a GS-14/15 inside a national cyber or intelligence organization — in command, operations, or senior advisory roles where they owned mission outcomes rather than briefed them. You know how targeting, authorities, tasking, and assessment actually work, because you have driven the machinery.
You will translate a defined company strategy into an executable plan for your accounts, and you will lead the people to execute it. Deployment Managers and Forward Deployed Analysts are assigned to your lines of effort — you decide how they are resourced, what they work on, and what good looks like, and you are accountable for the outcomes that team delivers.
What You’ll Do
Execution against account strategy
Translate company strategy into the deployment and operationalization plan for a portfolio of accounts within a command — approach, growth, training model, and staffing posture — built from scratch where none exists.
Direct a team of Deployment Managers and Forward Deployed Analysts assigned to your account: set their lines of effort, resource them to mission priority, hold the standard, and own what the team delivers.
Own the framing and positioning for renewal and growth conversations, using account-wide engagement metrics and competitive context to make the case.
Serve as a trusted advisor to senior leadership
Serve as Twenty's primary interface to task force and command leadership (O-5, O-6, GS-15): what the product is doing for the mission, where it goes next, and how it changes force employment.
Build and sustain a champion network across the account, from mission team and task force technical leads up to commanders and their senior civilians, and turn those relationships into deep cross-functional advocacy.
Brief senior leadership (SES, GOFO) on mission impact serving their priorities — operational outcomes, force generation, and resourcing.
Define successful force and capability employment across an organization
Shape the account's training strategy and the systems that scale it: standard curricula, train-the-trainer models, and institutional channels (J7 curriculum, JQR standards) that outlive any one engagement.
Translate mission requirements into product direction — own the engagement strategy for new capability from alpha through production release, and mentor your team on how to diagnose the true capability gaps and requirements that Twenty is postured to address.
Understand and orient your team and company leadership to what is true in the ambiguous field operating picture across the portfolio: users, stakeholders, workflows, blockers, adoption signals, risks, and value stories.
Mentor the Deployment and Forward Deployed Analyst team, and help set the talent bar as the team scales.
Who You Are
You came out of CYBERCOM, SOCOM, NSA, or CIA — most likely as an O-5/O-6, a Warrant Officer, or a GS-14/15. You held a command, a task force deputy or operations role, a technical directorate, or a senior advisory seat where the mission outcome was yours to answer for.
12+ years in offensive cyber, cyber operations, or intelligence operations, including 5+ years in a leadership or senior advisory role at USCYBERCOM, NSA, or CIA.
Leader or technical director of a cyber mission element, task force, or operations directorate — CNMF, a JFHQ-C, a CMT/CST construct, an NSA operations or technical directorate, or a CIA or SOCOM equivalent.
Track record of advising a commander or senior executives on operational employment: what to task, what to accept, what to stop, and what the authorities allowed.
Owned targeting, mission planning, execution support, or assessment at a level where you shaped the campaign, not just the engagement.
Sat in requirements, capability development, or acquisition conversations and know how a capability actually reaches an operator — and where that path usually breaks.
Ability to learn complex software quickly and explain it credibly to operators, targeters, program staff, and flag-level leadership.
Strong written communication. You turn ambiguous field input into concise requirements, decision memos, and executive-ready summaries.
Prior experience in a commercial product, deployment, or capability-delivery role supporting national security customers is a plus, not a requirement.
You are technically credible without being the engineer in the room. Operators respect you because you have been one or led them; leadership listens to you because you tell them the uncomfortable part first. You are comfortable operating with wide latitude — you build the plan, then run it.
Occasional travel for customer engagements, training, and mission support is required.
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.
If this role sounds like you, apply and share with us your interest
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.