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About the Role
Twenty builds AI-enabled technology for mission-critical cyber operations. We're seeking a Staff Product Manager to help make agentic AI systems measurable, reliable, and continuously improvable. You’ll partner with AI and engineering teams to shape evaluation capabilities—from defining agent performance and product quality to turning results into useful workflows and product decisions.
Responsibilities
- Own or support the product roadmap for agentic AI evaluations, translating product-area goals into clear priorities and outcomes.
- Partner closely with engineering and AI teams to understand evaluation needs, technical constraints, and user workflows.
- Define how agent performance and product quality should be assessed, including useful measures of task success, reliability, and quality.
- Turn technical evaluation needs into clear product requirements, workflows, and acceptance criteria.
- Help operationalize evaluation workflows and success metrics so teams can consistently assess agent behavior and product changes.
- Use evaluation results and feedback to identify gaps, inform product decisions, and improve the agent experience over time.
Requirements
- Strong product experience with AI or agentic systems, including experience building or managing agentic systems through product work.
- Experience directly building evaluations for agents or building the evaluation product, tooling, or system used to assess them.
- Ability to translate technical evaluation needs into product requirements, priorities, and workflows in partnership with engineering and AI teams.
- Ability to define or operationalize meaningful measures of agent performance and product quality.
- Strong communication, collaboration, and product judgment in an evolving, technically complex environment.
- Experience in cybersecurity, offensive cyber, government, defense, intelligence, or another mission-driven environment.
- Familiarity with evaluation approaches such as benchmarks, human or automated evaluation, regression testing, simulation, or analysis of agent traces.
- Experience working with products that combine autonomous systems with meaningful human judgment and oversight.
- U.S. Citizenship Required
- No Active Clearance Required
Skills
- AI
- Agentic systems
- Product management
- Evaluation capabilities
- Agent performance
- Product quality
- Workflows
- Product decisions
- Technical curiosity
- Product judgment
- Collaboration
- Communication
- Metrics
- Cybersecurity
- Offensive cyber
- Government
- Defense
- Intelligence
- Benchmarks
- Human evaluation
- Automated evaluation
- Regression testing
- Simulation
- Analysis of agent traces
- Autonomous systems
- Human judgment
- Oversight
Location
- Arlington, Virginia
Work Type
- On Site
- Full Time
Experience Level
- Staff
Benefits
- Medical, dental, and vision plan options
- Life / AD&D, disability coverage options
- Paid parental leave for eligible full-time employees
- Paid holidays and flexible PTO
- 401(k) with pre-tax and Roth options
- HSA/FSA options, dependent care FSA
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.
Equal Opportunity
- 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.