Staff / Principal Technical Program Manager

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.

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 integration and deployment work.

• You say a date is at risk while there is still time to do something about it, and you say it in plain terms.

• PMs and EMs trust you because you help fix the problems you find.

• You hold product, engineering, and leadership to the same standard, and people on every side trust your read of the plan.

• You use data on estimates and outcomes to make planning better each cycle, and you share it in a way that helps teams improve.

• You write for two audiences: engineers who need the detail and executives who need the decision.

• You're motivated by mission work, where a missed date affects a customer's operation.

What You'll Do

• Run the planning cycle from intake through close-out. Lead planning sessions with PMs and EMs, and make sure requirements are clear enough to break down and design against before a team commits to the work.

• Hold teams to the planning process. When a step gets skipped, work with the PM and EM to get it back on track, and bring it to the VPs only when the teams can't resolve it themselves.

• Maintain the sizing standard, question estimates that don't hold up, and track estimates against actual effort so that they improve over time.

• Own the rolling delivery forecast, with dates and confidence levels.

• Run the status cadence across all active work, and produce the program-level rollup for executive leadership.

• With the deployment managers, maintain the register of deployment milestones, link each one to the roadmap work it depends on, and review milestone health with them regularly.

• When a roadmap change affects a milestone, make sure the PM, the deployment manager, and the right VP make the tradeoff explicitly.

• Maintain the map of dependencies between teams and the program risk register.

• Run end-of-cycle retros on how well plans matched results, and improve the planning process from what they show.

Must Have

• You have 10+ years of experience in software organizations, including at least 7 years owning delivery planning across multiple teams as a technical program manager, engineering manager, or technical lead.

• You have a software engineering background, or enough hands-on technical depth to read a design and judge whether its estimate is credible.

• You can read a product requirements document and judge whether it's ready for engineering to break down and design against. When it isn't, you can say what's missing.

• You learn a product and its customers' domain in enough depth to understand what each piece of work is for and whether or not its requirements, design, and estimate fit together.

• You've run a recurring planning cycle for multiple teams, from intake through commitment and close-out, and you can describe what you changed when it wasn't working.

• You've owned a delivery forecast or set of committed dates that leadership relied on, and you can show how you measured and improved its accuracy.

• You've held people at every level, executives included, to the commitments they made, and kept their trust while doing it.

• You've tracked engineering work against external commitments, such as customer deployments, contract milestones, or dates other organizations depended on.

• You write clear, concise status reporting for engineering teams and for executives.

• You must be eligible to obtain a U.S. Government security clearance.

Nice to Have

• You have experience in defense, intelligence, or national security technology programs.

• You've coordinated software deployments to customer-controlled environments, such as private cloud, on-premises, or classified networks.

• You've designed a planning process from scratch at a growing company.

• You hold an active 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.