Dir, Software Engineering

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. Role Summary You will own the engineering organization for our flagship analyst product — deployed across both Twenty's cloud and customer private cloud environments. You will lead a set of engineering managers and their teams spanning platform infrastructure, enterprise capabilities, and the full suite of customer-facing product features. You are ultimately accountable for the technical success of the product. This is not a role for someone who manages from a distance. You'll need the architectural judgment to engage credibly with senior ICs on hard technical problems, the organizational instincts to structure and scale a growing engineering org, and the execution discipline to keep multiple teams moving in parallel against a demanding roadmap. You'll partner closely with the product manager on roadmap and priorities, and with the VP of Engineering on org strategy and hiring. Day to day, you'll supervise and develop your engineering managers, balance capacity across teams, resolve cross-team dependencies, and drive the structural decisions — team composition, scope boundaries, sequencing of splits — that determine how this engineering org scales. Who You Are - You lead through managers: you develop them, hold them accountable, and build the systems that let them succeed independently. - You have the technical depth to engage meaningfully on architecture and design with senior ICs—you don't need to write the code, but you need to understand it. - You think at the org level: headcount, team structure, scope boundaries, and sequencing are as natural to you as roadmap and delivery. - You execute with rigor and communicate with clarity—up to VP and across to peers, without losing the technical truth. - You thrive in hybrid deployment environments: you understand the operational complexity of software that lives both in cloud and on customer-controlled infrastructure. - You hold a high bar and create the conditions for others to meet it—through clarity, coaching, and accountability. - You bring calm, structured decision-making to ambiguous, fast-moving problem spaces. What You'll Do - Own engineering execution across the product: delivery, quality, and technical accountability across all teams. - Lead, develop, and hold accountable a set of engineering managers; build their capacity to run their teams independently. - Drive org design decisions: team scope, composition, sequencing of team splits, and addition of new management capacity as the org grows. - Balance engineering capacity across teams; make explicit prioritization calls when demand exceeds supply. - Own the technical roadmap in partnership with the product manager, who owns the product and feature roadmap. - Engage at the architecture level with senior ICs—reviewing designs, providing guidance, and ensuring technical coherence across the platform. - Supervise hiring across engineering teams: set the bar, calibrate across managers, and close strong candidates. - Partner with the VP of Engineering on org strategy, headcount planning, and cross-product engineering initiatives. - Communicate clearly to senior leadership on progress, risks, and tradeoffs across the roadmap. - Ensure engineering practices—security, quality, reliability, and operational discipline—meet the standards required for mission-critical deployments. Must Have - You have 8+ years of professional software engineering experience. - You have 5+ years of engineering management experience, including at least 3 years managing other engineering managers. - You have a track record of owning engineering execution across multiple teams simultaneously, with high quality and clear accountability. - You have the architectural judgment to engage credibly with senior ICs: reviewing designs, identifying risks, and providing technical guidance across a complex, multi-layer stack. - You've owned org design decisions: team structure, scope boundaries, and how to sequence growth as headcount scales. - You've managed engineering organizations serving both cloud-hosted and on-premises or customer-controlled deployment environments. - You've partnered with product managers to translate operational requirements into technical roadmaps and delivery plans. - You've supervised hiring across multiple teams: setting the bar, calibrating across managers, and running a structured, high-signal process. - You must be eligible to obtain a U.S. Government security clearance. Nice To Have - You have experience in defense, intelligence, or national security technology environments. - You've led engineering organizations building operational platforms for government or mission-critical customers. - You've worked with graph databases or graph-based modeling for complex analytical problems. - You've led teams shipping enterprise features: multi-tenancy, RBAC, audit logging, or similar. - You have experience with secure development practices for government or controlled environments. - You've scaled an engineering organization through a rapid growth phase, including adding management layers. Tech Environment (You Might Work With) - React + TypeScript for user-facing applications and shared UI components - Go (and sometimes Python) for backend services and integrations - Neo4j and graph-based data modeling for core platform capabilities - PostgreSQL, Terraform, Ansible, and infrastructure-as-code - AWS, Docker, Kubernetes, CI/CD, and observability tooling - Customer private cloud deployment and on-site operational environments 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 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 . Twenty is an equal opportunity employer. We consider all qualified applicants without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, age, veteran status, disability, or any other protected status, consistent with applicable law. If you need a reasonable accommodation during the hiring process, let us know and we will work with you.