Forward-Deployed Security Engineer — Flexible Hours

aikidosecurity; Chicago (IL); On-site; USD 120,000 - 190,000; Full time

Job summary

Aikido Security is seeking a forward-deployed engineer to help enterprise customers deploy and operationalize our AI-powered pentest product. You’ll own deployments end-to-end, from initial install to a stable, healthy system, and work directly in customer environments to debug and optimize integrations.

Based in Chicago, you will navigate complex enterprise networks, read Go/TypeScript or Python code to trace issues, and translate incidents into clear bugs and product improvements.

Qualifications

• Strong infrastructure and networking fundamentals (Docker, DNS, TLS, proxies, firewalls).
• Comfortable debugging in Linux environments.
• Able to read Go, TypeScript, or Python to understand issues and trace problems.
• Familiar with how complex enterprise networks behave in practice.
• Basic offensive security knowledge: understand concepts like RCE, SSRF, and session handling.
• Able to interpret logs and debug distributed systems’ behavior.
• Strong communication skills.
• Based in Chicago.

Responsibilities

• Own enterprise deployments end-to-end: from first install to a stable, healthy setup
• Debug incidents directly in customer environments (Docker, Postgres, networking, agents, etc.)
• Handle complex enterprise environments: proxies, firewalls, egress rules, internal CAs, air-gapped setups, and custom security requirements
• Build and adapt integrations when needed (SSO, IdP, internal PKI, custom setups)
• Guide customers through implementation and initial usage in complex environments
• Improve deployment and update flows based on what actually breaks in the field
• Act as the technical bridge between customers and engineering
• Translate enterprise deployment issues into clear bugs, fixes, and product improvements
• Investigate agent behavior: debug failures, auth issues, crashes, and unexpected behavior

Skills

Infrastructure fundamentals

Linux debugging

Go/TypeScript/Python reading

Enterprise networks

Offensive security concepts

Log analysis

Communication

Chicago-based

Tools

Docker

DNS

TLS

Proxies

Firewalls

Job description

Aikido Security is seeking a forward-deployed engineer to help enterprise customers deploy and operationalize our AI-powered pentest product. You’ll own deployments end-to-end, from initial install to a stable, healthy system, and work directly in customer environments to debug and optimize integrations.

Based in Chicago, you will navigate complex enterprise networks, read Go/TypeScript or Python code to trace issues, and translate incidents into clear bugs and product improvements.