Staff / Principal Technical Program Manager

Twenty • Arlington, VA

9d • $124,000 - $257,000

About The Position

Twenty Technologies is hiring a Staff / Principal Technical Program Manager to run how its product and engineering teams plan and commit. Reporting to the VP of Engineering, this role owns the planning cycle from intake through close-out, including its calendar, stages, weekly status cadence, and delivery forecast. The program manager ensures requirements are ready for engineering to design against, estimates are credible, and delivery dates have honest confidence levels, while product managers determine what and when to build and engineering managers determine how and by whom it is built.

The role also connects roadmap work to government-customer deployment milestones. In partnership with deployment managers, the program manager maintains a register of commitments, links milestones to the roadmap work they depend on, and ensures changes to commitments are explicit decisions made by the appropriate owners. The role is neutral across product, engineering, and leadership: it holds teams and executives to their commitments, raises divergence between plans and results early, and escalates unresolved decisions to the VP of Engineering or VP of Product.

The ideal candidate keeps planning rigorous without creating unnecessary bureaucracy, has sufficient technical depth to evaluate estimates and requirements, and communicates clearly to both engineering teams and executives. The work supports mission-driven software deliveries where missed dates can affect customer operations. Twenty Technologies, founded in 2024 and headquartered in Arlington, Virginia, builds offensive cyber operations capabilities for the U.S. and its allies.

Requirements

• 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.
• A software engineering background, or sufficient hands-on technical depth to read a design and assess whether its estimate is credible.
• Ability to assess whether product requirements documents are ready for engineering breakdown and design, and to identify what is missing when they are not.
• Ability to learn a product and its customer domain well enough to assess whether requirements, design, and estimates fit together.
• Experience running a recurring, multi-team planning cycle from intake through commitment and close-out, and describing how it was improved.
• Experience owning a delivery forecast or committed dates relied on by leadership, and measuring and improving forecast accuracy.
• Experience holding people at every level, including executives, accountable to commitments while maintaining their trust.
• Experience tracking engineering work against external commitments such as customer deployments, contract milestones, or dates other organizations depend on.
• Ability to write clear, concise status reports for engineering teams and executives.
• Must be eligible to obtain a U.S. Government security clearance.
• Must be a U.S. citizen due to U.S. government contract and security requirements.

Nice To Haves

• Experience in defense, intelligence, or national security technology programs.
• Experience coordinating software deployments to customer-controlled environments such as private cloud, on-premises, or classified networks.
• Experience designing a planning process from scratch at a growing company.
• Active U.S. Government security clearance.
• Experience building program tracking and reporting in Linear, Notion, Jira, Confluence, or equivalent tools, including automated status rollups.
• Experience using AI tools to reduce manual work in status reporting, tracking, and risk monitoring.

Responsibilities

• Run the planning cycle from intake through close-out, including planning sessions with product managers and engineering managers.
• Ensure requirements are clear enough for teams to break down and design against before committing to work.
• Hold teams to the planning process, working with product and engineering managers to address skipped steps and escalating to vice presidents when teams cannot resolve issues.
• Maintain the sizing standard, question estimates that are not credible, and track estimates against actual effort to improve them over time.
• Own the rolling delivery forecast, including dates and confidence levels.
• Run the status cadence across active work and produce program-level rollups for executive leadership.
• Partner with deployment managers to maintain a register of deployment milestones, link milestones to dependent roadmap work, and regularly review milestone health.
• Ensure roadmap changes that affect deployment milestones result in explicit tradeoff decisions by the product manager, deployment manager, and appropriate vice president.
• Maintain the map of dependencies between teams and the program risk register.
• Run end-of-cycle retrospectives comparing plans with results and improve the planning process based on findings.
• Raise divergence between plans and results early and work with the relevant people to resolve it.
• Hold product, engineering, and leadership accountable to their commitments and escalate decisions that cannot be resolved at team level.

Benefits

• Medical, dental, and vision plan options.
• Life and AD&D coverage options.
• Disability coverage options.
• Paid parental leave for eligible full-time employees: 12 weeks for birthing parents, 4 weeks for non-birthing parents, and 6 weeks for adoptive, foster, or intended parents through surrogacy.
• Paid holidays and flexible PTO.
• 401(k) with pre-tax and Roth options.
• HSA/FSA options and dependent care FSA.

What This Job Offers

• Job Type: Full-time
• Career Level: Senior
• Education Level: No Education Listed