Staff Product Manager - AI Evals

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.

Qualifications

• Nice to Have: Experience in cybersecurity, offensive cyber, government, defense, intelligence, or another mission-driven environment.
• Nice to Have: Familiarity with evaluation approaches such as benchmarks, human or automated evaluation, regression testing, simulation, or analysis of agent traces.
• Nice to Have: Experience working with products that combine autonomous systems with meaningful human judgment and oversight.

Benefits

• 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.

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.

Pay

Compensation Range: $161K - $389K