Twenty is a cyber warfare startup that builds AI-enabled, end-to-end offensive cyber systems for the U.S. military and the Intelligence Community.
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 http://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. ROLE SUMMARY The Mission Architect is the senior domain expert embedded on a product team to ensure what gets built matches how users actually work. You will turn real operational workflows, constraints, and edge cases into clear product requirements, testable acceptance criteria, and high-fidelity user experiences. You will partner closely with Product Managers, engineers, designers, and researchers to keep product decisions grounded in reality. This role is for someone who has deep credibility in their field and wants to shape software that materially improves outcomes for practitioners. WHO YOU ARE - You bring real credibility in your domain and instinctively separate what sounds good in theory from what works in practice. - You care deeply about building products that hold up under real operational pressure, not just in ideal test conditions. - You are comfortable working through ambiguity and turning messy, incomplete inputs into clear direction for a team. - You communicate clearly across audiences, from hands-on practitioners to senior leaders. - You raise the quality bar by being exacting about workflows, usability, and what “done” actually means for the user. - You collaborate well with product and engineering teams, even when they do not share your domain background. - You are trusted to bring direct feedback, sound judgment, and a practical point of view to difficult trade-offs. WHAT YOU’LL DO - You will translate complex user workflows, decision points, and constraints into clear requirements and user stories that engineering can build from. - You will partner with the Product Manager to shape PRDs, refine scope, and ensure roadmap items reflect real user needs. - You will define and refine acceptance criteria so delivered work is validated against operational reality, not just technical correctness. - You will run the product through realistic end-to-end scenarios and surface usability issues, workflow gaps, and edge cases early. - You will review features before release and confirm they behave correctly in the way users actually work. - You will design evaluation scenarios, scoring approaches, and benchmark workflows that measure real user impact. - You will shape workflows, information architecture, and interface behavior so the product feels native to the domain. - You will serve as the product team’s primary domain expert, helping engineers, designers, and researchers make better decisions faster. - You will support customer conversations and demonstrations, translating product capabilities into language that resonates with practitioners and leadership. - You will surface emerging user needs, new use cases, and deployment opportunities that inform future product direction. MUST HAVE - You have 7+ years of hands-on experience as a practitioner in the product’s target domain, such as cyber operations, intelligence analysis, capability acquisition, or a comparable field. - You have strong credibility with practitioners in that domain and a track record of trusted judgment in high-stakes work. - You have experience translating complex operational workflows into structured product requirements, user stories, or other build-ready documentation. - You have helped shape user-facing tools, workflows, or interfaces used in real operational environments. - You have strong written and verbal communication skills across technical, operational, and executive audiences. - You have experience working cross-functionally with Product, Engineering, and related teams. - You have strong judgment for defining acceptance criteria and evaluating whether a feature truly meets user needs. NICE TO HAVE - You have transitioned from a practitioner role into product development, requirements engineering, or capability development. - You have worked with AI/ML-powered products, including agentic systems, LLM-based workflows, or knowledge graph applications. - You have experience in evaluation design, operational test and evaluation, or scenario-based product assessment. - You have created training content, reference materials, or doctrine for operational users. - You have influenced product direction at a software company serving government or defense customers. TECH ENVIRONMENT (YOU MIGHT WORK WITH) - You might work with AI/ML-powered product experiences, including LLM-driven and agentic workflows. - You might work with knowledge graph applications and products built around complex data relationships. - You might work with evaluation tooling, scenario libraries, scoring rubrics, and acceptance benchmark frameworks. - You might work closely with modern product and engineering teams shipping user-facing software for operational environments. SECURITY / WORK ENVIRONMENT Some positions may require an active U.S. Government security clearance, depending on the product’s customer environment. This role may involve work in a controlled environment. Benefits What's on the table: - Health. Medical, dental, and vision plan options. Life / AD&D, disability coverage options. - Family. Pa