Forward deployed engineer Chicago

Syndicate; Chicago, Northern (IL, KY); Hybrid; USD 120,000 - 160,000; Full time

Job summary

Aikido 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 first install to a healthy, running environment, including on-prem and hybrid cloud setups.

Based in Chicago, you will debug incidents in customer environments, work with Docker, Postgres, networking, and security controls, and translate issues into product improvements.

Qualifications

• Experience deploying enterprise software in on-prem or hybrid environments.
• Ability to debug issues in customer environments and translate them into bugs.
• Strong Linux troubleshooting and networking basics.
• Familiarity reading Go, TypeScript, or Python to trace problems.
• Excellent communication while working with customers.

Responsibilities

• Own enterprise deployments end-to-end from install to stable setup.
• Debug incidents in customer environments (Docker, Postgres, networking).
• Handle proxies, firewalls, and air-gapped setups in complex networks.
• Build integrations for SSO or PKI when needed.
• Guide customers through initial deployment and usage.
• Translate deployment issues into clear bugs and product improvements.
• Act as the technical bridge between customers and engineering.
• Investigate agent behavior and runtime incidents.
• Collaborate with customers to ensure successful deployment.

Skills

Docker

Networking fundamentals

Linux debugging

Go/TypeScript/Python reading

Problem-solving

Communication skills

On-prem & hybrid deployments

Customer deployment experience

Tools

DNS

TLS

Proxies

Firewalls

Job description

We’re making security suck less for developers.

Security tools haven’t kept up with how software is built today. They interrupt teams, slow releases, and turn security into a bottleneck instead of a capability. We built Aikido to change that. Aikido builds developer-first security products that reduce real risk without getting in the way of shipping software. We focus on what actually matters and automate the rest.

We’re taking on legacy security tools teams have been stuck with, and we’re winning. If you want to help us take market share and build products developers actually enjoy using, you’re in the right place.

Founded in 2022 by third-time founders, Aikido has $85M in the bank and a long runway ahead. We’re building toward self-securing software. Join an all-star team. Take real ownership. Push boundaries. Build things that matter. We’re looking for a forward-deployed engineer to help enterprise customers successfully deploy and operationalize our newly launched AI-powered pentest product into their environments.

Some deployments run fully on-prem. Others involve hybrid cloud setups, strict security controls, custom integrations, or heavily regulated enterprise environments. You’ll own everything from “customer signed” to “deployment running smoothly”, helping customers through implementation, debugging issues, and turning problems into product improvements.

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

• 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
• Lives in Chicago

Nice to have:

• Experience with enterprise or on-prem software deployments
• Familiarity with cloud environments (AWS, Azure, GCP) for hybrid setups
• Experience with SSO, identity providers, or internal PKI systems
• Exposure to security tooling or offensive security concepts

What you can expect:

• High-impact position in a fast-growing company.
• Competitive salary package.
• A company that sticks to its values in an open and informal atmosphere (see our culture page on the website for more details).
• A diverse and inclusive organization that is proud to be an equal-opportunity employer.
• Flexibility in working hours

We value competencies above all. The qualities of our people are what count, irrespective of gender, religion, ethnic origin, age, sexual orientation, or disability.