Staff / Principal Technical Program Manager
Runs the planning and delivery cadence for Twenty's product and engineering teams: owning the planning cycle, delivery forecast, status reporting, and the register of government deployment milestones. Requires deep TPM experience, technical depth, and eligibility for a U.S. government security clearance.
- Compensation
- $124K–$170K / yr
- Location
- Arlington, VA
- Work setup
- Onsite
- Seniority
- Principal
- Employment
- Contract
- Experience
- 7+ years
- Category
- Project management
- Posted
Skills
Must have
- 10+ years in software organizations, including 7+ years owning delivery planning across multiple teams as a TPM, engineering manager, or technical lead
- Software engineering background or enough hands-on technical depth to judge whether a design's estimate is credible
- Able to judge whether a product requirements document is ready for engineering to break down and design against
- Learns a product and its customers' domain in enough depth to evaluate requirements, design, and estimates
- Has run a recurring planning cycle for multiple teams from intake through commitment and close-out
- Has owned a delivery forecast or committed dates that leadership relied on, with measured accuracy improvements
- Has held people at every level, including executives, to their commitments while keeping their trust
- Has tracked engineering work against external commitments such as customer deployments or contract milestones
- Writes clear, concise status reporting for engineering teams and executives
- Must be eligible to obtain a U.S. Government security clearance
Nice to have
- Experience in defense, intelligence, or national security technology programs
- Coordinated software deployments to customer-controlled environments (private cloud, on-premises, or classified networks)
- Designed a planning process from scratch at a growing company
- Holds an active U.S. Government security clearance
- Built program tracking and reporting in Linear, Notion, Jira, or Confluence, including automated status rollups
- Used AI tools to reduce manual status reporting, tracking, and risk monitoring work
Full description
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 () 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.