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 We are seeking a DevOps Engineer / Software Engineer – Infrastructure for an in-office position in our New York, NY office focused on infrastructure and reliability to help design, build, and operate our application platform. This position is at the crossroads of software engineering, operations, and security. You will own core AWS infrastructure, drive observability and reliability improvements, and collaborate closely with product and backend teams. Common backgrounds for this role include DevOps Engineer, SRE, Platform Engineer, or Backend Engineer (Infrastructure). WHAT YOU’LL DO - Design, build, and operate AWS-based infrastructure. - Implement and maintain Infrastructure-as-Code for single-tenant and multi-tenant environments using Terraform. - Build and maintain deployment and environment automation (Ansible or similar). - Own and evolve CI/CD pipelines. - Design, implement, and refine observability: metrics, logs, traces, dashboards, and alerting. - Partner with application teams on architecture decisions, performance tuning, and operational readiness. - Contribute to security and governance: IAM policies, network security, secrets management, and security scanning. - Document systems, patterns, and runbooks so others can operate and extend the platform reliably. MUST HAVES - Experience administering infrastructure and operating applications deployed on AWS. - Experience using Terraform to manage single-tenant and multi-tenant systems. - Strong instincts and practical experience with: - IP networking (VPCs, routing, subnets, proxies, DNS). - Network security (security groups, NACLs, firewalls). - PKI management (TLS certificates, CAs, mTLS, certificate lifecycle). SHOULD HAVE - Experience with Ansible or another deployment automation/configuration management framework. - Experience with GitHub Actions or another CI/CD platform (GitLab CI/CD, CircleCI, etc.). - Experience working on reliability projects, such as: - Setting up alert management tools and on-call practices. - Debugging failures in distributed systems. - Experience setting up observability and operations programs, including: - Collecting and representing telemetry in Grafana (dashboards, panels, alerts). - Instrumenting applications using OpenTelemetry or other log/metric/trace aggregation frameworks. - Experience managing PostgreSQL databases in production (backups, migrations, performance, monitoring). - Experience managing a pub/sub or queue technology, such as NATS, RabbitMQ, Kafka, AWS SQS, or Google Pub/Sub. - Familiarity with secrets management (AWS SSM/Secrets Manager, Vault, or similar). NICE TO HAVE - Experience or strong interest in cybersecurity (threat modeling, hardening, secure defaults). - Proficiency in Python or another scripting language for tooling and automation. - Experience operating a security scanning tool, such as Trivy (or similar vulnerability/container scanners). - Experience or interest working with large datasets (performance, storage trade-offs, retention policies). - Experience managing graph databases, such as Neo4j, AWS Neptune, or similar. - Experience designing or contributing to runbooks and internal platform documentation for non-infrastructure teams. 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.