Staff / Principal Technical Program Manager

The posting, as Twenty wrote it

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 http://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 run how Twenty's product and engineering teams plan and commit. You'll own the planning cycle: the calendar, each stage from intake through close-out, the weekly status cadence, and the delivery forecast that leadership relies on. Product managers decide what gets built and when. Engineering managers decide how it gets built and who builds it. You make sure both follow the planning process, that requirements are ready for engineering to design against, that estimates hold up, and that every date comes with an honest confidence level.

Our software ships to government customers, and much of our roadmap is tied to deployment milestones that customers and missions depend on. Working with our deployment managers, you'll keep a register of those commitments, link each one to the roadmap work it needs, and make sure that when priorities change, the tradeoff against a commitment is made explicitly and on the record by the people who own it. Done well, this means customers and missions can count on what we've promised them, because any change to a commitment is a decision the right people made together.

You'll report to the VP of Engineering and work alongside your peers, Twenty's product managers, engineering managers, and deployment managers. The role is neutral: you hold everyone to the commitments they make, from individual teams to executive leadership. When plans and results start to diverge, you raise it early and work it through with them. When a problem needs a decision above the teams, you have the standing to take it directly to the VP of Engineering or the VP of Product. At Twenty, ideas are easy and execution is everything. This role keeps our pace aggressive and predictable at the same time.

WHO YOU ARE

• You keep plans honest without turning planning into bureaucracy. Teams leave your sessions with a clearer plan and less overhead.
• You have the engineering depth to question an estimate on its merits. You can tell when a size ignores a team's past velocity or leaves out integrati

[…]
ive U.S. Government security clearance.

• You've built program tracking and reporting in Linear, Notion, or equivalents such as Jira and Confluence, including automated status rollups.
• You've used AI tools to cut the manual work of status reporting, tracking, and risk monitoring.

TECH ENVIRONMENT (YOU MIGHT WORK WITH)

• Product and engineering teams building in Go, Python, React, and TypeScript
• AWS, Terraform, Ansible, Docker, and CI/CD pipelines
• Deployments to Twenty's cloud, customer private clouds, and on-site customer environments
• Linear and Notion, or equivalents such as Jira and Confluence, for planning, tracking, and documentation

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.