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 | U.S. Citizenship Required / No Active Clearance Required

Role Summary

You will build and lead the engineering organization that gets Twenty's software into the environments where our customers use it, keeps it secure and running there, and keeps it accredited. That covers infrastructure and the delivery path into customer environments, security engineering for our products, site reliability engineering at headquarters and at customer sites, and a new accreditation program for our products on government networks.

You will decide what gets built first, hire the people who build it, and lead them directly while the organization grows, often in disciplines where they know more than you do. You'll need enough technical depth to lead those specialists credibly, the judgment to make sound decisions in areas you haven't worked in yourself, and the organizational instincts to grow a new function.

Our product engineering teams are your peers and your main customers. You succeed by giving them tools, defaults, and a delivery path they want to use, not by doing their work for them. You'll partner closely with the VP of Engineering on org strategy and hiring, and with the product engineering leaders on what this organization provides them.

• Build the organization: decide what to stand up first, how the work is divided into teams, and when to add management capacity, in partnership with the VP of Engineering.
• Hire across infrastructure, security, reliability, and accreditation: set the bar for each discipline, run a structured process, and close strong candidates in a cleared hiring market.
• Lead and develop senior engineers directly, as well as the managers you add as the organization grows.
• Own the delivery path from a developer's laptop to a running instance, including instances we can't reach interactively: build, signing, packaging, install, upgrade, and rollback in customer environments.
• Take over infrastructure work that product teams are doing today, and build a team resilient enough to keep owning it.
• Own the operation of our products in our cloud and at customer sites, including incident response across the boundary between them.
• Lead security engineering for our products: design review, secure defaults, vulnerability management, and detection, working with our managed detection and response provider.
• Stand up and own an accreditation program for our products, through a dedicated lead who reports to you.
• Communicate clearly to senior leadership on progress, risks, and the tradeoffs you're making.Who You Are
• You're equally comfortable in a data-model review, a customer conversation, and a 1:1—you bring the same rigor to each.
• You think in systems: data pipelines, marketplace incentives, interfaces, trust boundaries, team structure, and delivery dependencies—not just tickets.
• You can turn ambiguous operational needs into clear engineering problems, measurable product outcomes, and executable plans.
• You hold a high bar without creating drag—you know when to push and when to get out of the way.
• You execute: you drive projects to completion, make decisions under uncertainty, and actively resolve ambiguity before it becomes drift.
• You communicate crisply with engineers, product partners, operators, vendors, and leadership without losing technical truth.
• You bring calm, structured decision-making to sensitive, fast-moving problem spaces where data quality, privacy, and security matter.

Must Have

• You have 8+ years of professional experience across software, infrastructure, site reliability, or security engineering.
• You have 5+ years of engineering management experience, including leading multiple teams or a team spanning more than one discipline.
• You've built or substantially rebuilt an engineering function: set its scope, hired its people, and grown it into a team others rely on.
• You've led senior engineers in disciplines outside your own background, and can describe how you judged their work.
• Your organization has owned production systems in operation, including on-call, incident response, and the postmortem and root cause analysis (RCA) process.
• You've led teams supporting software deployed outside a standard cloud environment: on-premises, private cloud, restricted, or customer-controlled infrastructure.
• You've run hiring across multiple roles: setting the bar, running a structured process, and closing strong candidates.
• You must be eligible to obtain a U.S. Government security clearance.

• You've managed engineering managers.
• You have experience in defense, intelligence, or national security technology environments.
• You've worked with accreditation or authorization processes for government systems, or with compliance frameworks such as CMMC, SOC 2, or NIST 800-53.
• You've led forward-deployed or on-site engineering teams working inside customer environments.
• You've owned software delivery into disconnected or restricted networks.
• You've managed a relationship with a managed detection and response provider or an outsourced security operations function.
• You've built an internal platform that product teams adopted by choice.

Tech Environment (You Might Work With)

• AWS, Terraform, Ansible, and infrastructure as code
• Docker, Kubernetes, CI/CD, artifact signing, and release engineering
• Self-hosted observability across cloud and customer environments
• Services in Go, Python, and TypeScript, backed by PostgreSQL and Neo4j
• Customer private cloud, restricted, and classified deployment environments
• Managed detection and response, vulnerability management, and identity and access tooling

• 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 .