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 You will own and drive products that directly support offensive cyber missions, turning real operational needs into scalable, high-impact software. This is a product role for someone who is comfortable in ambiguity, can make hard decisions, and knows how to prioritize outcomes over process. You will work closely with engineers, operators, and leadership to shape mission-critical capabilities used by experts under pressure. The problems are complex, the environments non-standard, and the products you build will be used in real operations where reliability and clarity matter. WHO YOU ARE - You are energized by hard, ambiguous problems where there is no obvious playbook. - You are motivated by building software that has direct operational impact, not just shipping features. - You have strong judgment and handle sensitive work with discretion and maturity. - You are comfortable working closely with technical teams and expert users, even when requirements are incomplete or evolving. - You bring a pragmatic, outcomes-first approach and know when to push for speed versus long-term durability. - You communicate clearly and directly, whether you are aligning engineers, operators, or leadership. - You are curious about offensive cyber and adjacent mission domains, even if you have not worked in them before. - You are at your best in small, high-trust teams with high standards and real ownership. - You are comfortable in high-speed, high-stakes environments, and take the initiative to solve problems even when they fall outside your direct job role. WHAT YOU’LL DO - Own product vision, strategy, and execution for one or more mission-critical capabilities. - Work directly with engineers to shape requirements, define scope, and sequence delivery. - Partner closely with operational stakeholders to understand workflows, constraints, and what success looks like in practice. - Translate complex technical and operational needs into clear product requirements, priorities, and roadmaps. - Balance near-term delivery needs with longer-term platform and capability development. - Drive product decisions using a mix of user feedback, qualitative insight, and technical understanding. - Support products deployed in constrained or non-standard environments, including bespoke or air-gapped infrastructure. - Help the team focus on the highest-leverage problems and make sound tradeoffs under pressure. - Create alignment across engineering, operators, and leadership on what to build, why it matters, and what comes next. MUST HAVE - You have 4+ years of experience building products. - You have experience as a Product Manager or in a closely related role, such as technical program manager, founder, or engineer with meaningful product ownership. - You have worked closely with tech leads and engineering leadership to plan, prioritize, and sequence product roadmaps. - You have strong technical fluency and can engage meaningfully with engineers on architecture, tradeoffs, feasibility, and delivery risk. - You have shipped complex products in high-stakes, ambiguous, or low-signal environments. - You have sound judgment and discretion when working with sensitive customers, systems, or problem spaces. - You have clear written and verbal communication skills and can turn complexity into clarity for different audiences. NICE TO HAVE - You have experience with offensive cyber operations, cyber intelligence, red teaming, or adjacent domains. - You have experience building products for national security customers - You have built or managed AI-driven or agentic products. - You have used AI tools to accelerate product discovery, design, or software development. - You have a background in data platforms, analytics, knowledge graphs, or complex backend systems. - You have worked in government, defense, intelligence, or similarly mission-driven environments. TECH ENVIRONMENT (YOU MIGHT WORK WITH) - You might work with products deployed in air-gapped or bespoke infrastructure environments. - You might work with backend-heavy systems that support complex operational workflows. - You might work with data platforms, analytics systems, or knowledge graph-oriented capabilities. - You might work alongside teams building AI-driven or agentic product experiences. - You might work in environments where reliability, security, and operational usability matter as much as feature velocity. SECURITY / WORK ENVIRONMENT You must be a U.S. citizen and eligible to obtain a U.S. Government security clearance. 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. 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 opti