Senior /Lead AI Developer - W2

Robot Insight Technologies; Chicago (IL); On-site; USD 120,000 - 180,000; Full time

Job summary

Robot Insight Technologies is seeking a Senior / Lead AI Developer to drive enterprise modernization using agentic engineering workflows. You will triage legacy code, design modernization specs, and author AI skills to upgrade frameworks securely.

You will lead AI pods, migrate across Java/.NET while preserving architecture, and ensure cloud-ready runtimes with modern security. Expect hands-on leadership and rigorous verification gates.

Qualifications

• 7–10+ years in Software Engineering with incident experience and 1–2 years in AI/agentic projects.
• Experience building or configuring AI agents/workflows (Claude Code, Cursor, Copilot).
• Deep Java and/or .NET modernization expertise; Linux/Windows environments.

Responsibilities

• Design, author, and refine reusable AI skills and agents for modernization and verification.
• Lead AI-assisted development pods and migrations across Java/.NET ecosystems.
• Drive framework and runtime upgrades (JDK, JBoss, app servers) and token-based identity transitions (Okta, OAuth/OIDC/JWT).
• Break modernization into pod-ready increments and review outputs with human-in-the-loop verification.
• Troubleshoot build/runtime failures and production incidents with disciplined analysis.
• Mentor developers in agentic engineering, secure coding, and reusable failure modes.

Skills

7–10 yrs exp

Agentic engineering

APIs & CI/CD

Debugging & observability

Tools

Claude Code

Cursor

GitHub Copilot

JDK

JBoss

Job description

We are looking for a hands-on Senior / Lead AI Developer to drive enterprise application modernization using cutting-edge agentic engineering workflows. In this role, you will triage unfamiliar legacy codebases, design spec-driven modernization approaches, and author reusable AI skills and agents to safely execute framework and security upgrades.

You will lead AI-assisted development pods, guide safe tech-stack migrations across Java and .NET ecosystems, and ensure existing application architectures are preserved while upgrading to modern security and cloud-ready runtimes.

Key Responsibilities

• AI Agent & Skill Governance: Design, author, and refine reusable AI skills and agents for reverse engineering, dependency analysis, code transformation, migration, and automated verification.
• Architecture & Triage: Lead the reverse engineering of legacy and current-state enterprise applications (Java/.NET) to discover dependencies, integrations, database touchpoints, security flows, and runtime assumptions.
• Spec-Driven Modernization: Turn discovery findings into technical specifications and structured implementation plans for AI-assisted delivery pods.
• Tech-Stack & Security Upgrades: Drive framework and runtime upgrades (JDK, JBoss, application servers, dependencies) and guide the migration from legacy LDAP/authorization logic to modern token-based identity patterns (Okta, OAuth/OIDC/JWT).
• Technical Lead & Execution: Break modernization initiatives into pod-ready increments, review agent outputs and code changes, stay hands-on for high-risk components, and establish human-in-the-loop verification gates.
• Incident Management & Root Cause Analysis: Apply disciplined systems thinking to troubleshoot complex build/runtime failures and production incidents.
• Mentorship & Continuous Improvement: Mentor developers in agentic engineering, secure coding, and context engineering while capturing reusable failure modes, prompts, and verification steps.

Required Qualifications

• Experience: 7–10+ years in Software Engineering with production support/incident experience, plus 1–2 years of hands-on experience with agentic engineering and AI projects.
• AI Tooling & Agentic Engineering: Demonstrated experience building or configuring AI agents and workflows using tools such as Claude Code, Cursor, GitHub Copilot, or similar frameworks. Preference for Claude Code and custom agentic workflow development.
• Core Software Engineering: Deep expertise in Java (JDK, application servers like JBoss, Maven/Gradle) and/or .NET enterprise application modernization.
• Systems & Environment: Strong background in Linux/Red Hat and Windows server environments, understanding how OS, middleware, and database changes interact.
• Identity & Security: Understanding of legacy LDAP authentication/authorization and practical migration experience to token-based identity patterns (Okta preferred).
• Engineering Fundamentals: Strong command of APIs, SQL/databases, CI/CD pipelines, Git, debugging, observability, and secure software delivery.
• Systems Thinking: Ability to enter unfamiliar, large monolithic codebases, assess blast radius across downstream/upstream systems, and execute safe in-place upgrades without forcing unnecessary microservice decomposition.

Preferred Qualifications

• AI/LLM Stack: Proficiency in Python, modern LLM/agent frameworks, Model Context Protocol (MCP)/tool integration, prompt engineering, and RAG.
• Cloud & Platform: Experience with GCP / Vertex AI or enterprise cloud AI platforms.
• Application Security: Vulnerability remediation, software supply-chain controls, secrets management, OAuth2/OIDC, and JWT implementation.