Top Tech Jobs & Startup Jobs in Chicago, IL

Evaluate AI coding-agent interactions for usefulness, correctness, engineering judgment, reasoning quality, and developer trust. Provide clear, opinionated feedback, distinguish response-quality levels, and help define standards for excellent interactions with tools such as OpenAI Codex, Claude Code, and Cursor. This contract role requires staff- or principal-level software engineering experience and familiarity with modern AI-assisted development workflows.

Own the roadmap for an AI-powered document intelligence platform. Translate client and reviewer needs into technical requirements, user stories, business rules, and measurable acceptance criteria. Coordinate priorities across data engineering, data science, backend, search, and frontend teams. Define document-processing and review workflows, evaluate model quality, diagnose platform issues, manage releases and demos, and measure accuracy, completeness, latency, reliability, adoption, reviewer effort, and cost.

Evaluate AI coding-agent interactions for usefulness, correctness, engineering judgment, explanations, and trustworthiness. Provide clear written and video feedback, distinguish response quality levels, and help define standards for tools such as Codex, Claude Code, and Cursor. The role requires senior engineering experience, strong TypeScript/JavaScript or Python skills, familiarity with AI-assisted development, excellent English communication, and comfort making rigorous subjective judgments.

Evaluate AI coding agents such as Codex, Claude Code, and Cursor for engineering quality, reasoning, usefulness, and judgment. Provide rigorous written feedback, distinguish response quality levels, assess explanations without executing every line, and help define standards for effective AI-assisted development workflows. The role is remote, flexible, contract-based, and requires strong communication skills and senior-level software engineering experience.

Evaluate AI coding agents such as Codex, Claude Code, and Cursor for engineering judgment, reasoning quality, usefulness, correctness, and user trust. Provide detailed written and video feedback, distinguish response quality levels, and help define evaluation standards for strong AI-assisted development workflows. The role requires senior-level software engineering experience, strong TypeScript, JavaScript, or Python skills, familiarity with AI coding tools, and excellent English communication.

Evaluates AI coding-agent interactions for technical quality, engineering judgment, reasoning, explanations, and user trust. Provides detailed written and video feedback, distinguishes response quality levels, and helps define standards for tools such as Codex, Claude Code, and Cursor. This flexible, remote contract requires senior-level software engineering experience, strong TypeScript/JavaScript or Python skills, familiarity with AI-assisted development, and excellent English communication.

Own and optimize CI/CD pipelines, mobile and web build systems, deployment workflows, and release processes. Manage iOS and Android releases through Expo/EAS, App Store Connect, and Google Play Console. Configure OTA updates, versioning, testing, and A/B testing environments. Troubleshoot deployment failures and React Native bugs, make UI changes, improve Supabase and developer tooling, and support Next.js and React applications in a remote startup environment.

Evaluate AI coding-agent interactions for usefulness, correctness, engineering judgment, reasoning quality, and user trust. Provide rigorous written feedback, distinguish response quality levels, help define evaluation standards, and record short video explanations. The role requires senior-level software engineering experience, familiarity with AI-assisted development tools, strong TypeScript/JavaScript or Python skills, and excellent English communication.

Build, operate, and improve cloud infrastructure for FedRAMP-authorized environments, including AWS GovCloud, Kubernetes, Terraform, Ansible, CI/CD, observability, and security automation. Investigate production incidents, remediate vulnerabilities, support compliance and audits, and improve reliability, scalability, and monitoring. Collaborate with engineering, security, compliance, and international teams while making independent architectural and operational decisions.

The Staff Engineer at G2i will lead and grow an engineering team, set technical strategy, and ensure quality delivery across full-stack systems while fostering a culture of ownership and continuous improvement.