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 - Short decision lines. Big ownership. Shape the projects that matter and ship fast. - Grow as fast as we do. Take on more, own more, and carve out your own path. - Top-tier tech pay and equity. - High trust, strong values, zero corporate BS. - Flexibility in working hours. - A company that sticks to its values in an open and informal atmosphere. We hire for talent, drive, and potential. Everything else is noise.