Forward Deployed Engineer Chicago

**🌍 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