Senior/Staff DevOps Engineer

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.

About the Role

We are seeking a Senior/Staff DevOps Engineer 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).

Responsibilities

• 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.

Requirements

• 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).

Qualifications

• 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