Staff Product Manager - AI Evals

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.

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

U.S. citizenship required; 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

Benefits

Medical, dental, and vision plan options; Life / AD&D, disability coverage options; Paid parental leave for eligible full-time employees (12 weeks for birthing parents, 4 weeks for non-birthing parents, 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; Dependent care FSA