Staff Product Manager - AI Evals

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.

Mission |

On Site

| Full Time |

U.S. Citizenship Required / No Active Clearance Required

Role Summary

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.

The strongest candidates will bring meaningful experience building or managing agentic systems, either by directly building evaluations or by building the systems that enable teams to evaluate and improve agents. Cyber experience is a plus, but not required.

Who You Are

You're a product-minded, technically curious operator who is excited about how agentic systems work and how to make them better.

You bring strong product judgment and can turn complex technical needs into clear, usable product direction.

You enjoy partnering with engineers and AI teams, asking good questions, and working through ambiguity together.

You are rigorous about evidence and metrics, while recognizing that evaluation methods need to reflect real user and product needs.

You take ownership, communicate clearly, and are comfortable balancing learning, execution, and iteration.

What You’ll Do

• 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.
• Must Have
• 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.
• Nice to Have
• 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.

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.

If you need a reasonable accommodation during the hiring process, let us know and we will work with you.