Senior​/DevSecOps Engineer

Cybersecurity Engineer

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 industrializes offensive cyber operations for the U.S. and its allies. Headquartered in Arlington, Virginia, Twenty has raised $38M from Caffeinated Capital, General Catalyst, and In-Q-Tel.

You'll build and own the security infrastructure that keeps Twenty's engineering systems safe without slowing engineers down. This role spans runtime security, access control, secrets management, compliance, and CI/CD hardening—but it's equally about making security the path of least resistance. You'll embed with our engineering teams, design secure-by-default foundations, and build the tooling and automation that lets developers move fast without cutting corners.

You'll report directly to the VP of Engineering and operate as a shared function across our product teams.

• You believe security should be a force multiplier for engineering, not a gatekeeper.

• You take ownership end-to-end: from identifying a risk to designing the control to shipping the fix.

• You bring high judgment to tradeoffs—you know when to enforce hard controls and when friction kills adoption.

• You communicate clearly with both engineers and non-technical stakeholders, and you translate risk into plain language.

• You prefer automation over policy: if an engineer has to do something manually to stay secure, you see that as a bug.

• You hold a high bar for reliability and auditability in the systems you build.

• You're self-directed and thrive in an environment where the function is new and you're defining it.

• Own runtime security and vulnerability management across cloud and container environments, including triage, prioritization, and remediation tracking.

• Design and enforce identity and access management (IAM) across AWS and internal systems—least-privilege by default.

• Own secrets and credentials management: policies, tooling, rotation, and developer workflows that make doing the right thing easy.

• Lead security incident response: detection, containment, root cause analysis, and durable remediation.

• Manage AWS Organization structure, account boundaries, SCPs, and guardrails.

• Harden and maintain CI/CD pipelines, embedding security scanning and policy enforcement into the software delivery lifecycle.

• Drive compliance efforts—own the evidence, controls, and remediation work to meet and maintain relevant frameworks.

• Build and maintain secure-by-default templates for repos, pipelines, and infrastructure modules.

• Reduce friction through automation: certificate issuance, secrets access, policy-as-code, and developer-facing tooling.

• Produce lightweight, practical security guidance that engineers actually use.

• Shape the direction of the DSO function as it scales, and contribute to hiring and team-building as we grow.

• 8+ years in Dev Sec Ops , platform security, or a closely related security engineering role.

• Deep hands-on experience with AWS—IAM, SCPs, Organizations, security services (Guard Duty, Security Hub, Cloud Trail, etc.).

• Strong IaC experience with Terraform; you've used it to enforce security controls, not just provision infrastructure—and you've layered in policy-as-code tooling (e.g., OPA, Checkov, tfsec) or continuous compliance checks (e.g., AWS Config Rules) to catch drift and misconfigurations.

• Experience owning secrets management end-to-end in a production engineering environment.

• Proven track record designing and hardening CI/CD pipelines (we use Git Hub Actions).

• Hands-on experience with container security, including image scanning and runtime controls.

• Experience leading or meaningfully contributing to a compliance program; CMMC Level 2 (or NIST SP 800-171) experience strongly…