Top Tech Jobs & Startup Jobs in Chicago, IL

Develop, extend, and optimize game systems and rendering pipelines using O3DE with C++ and Lua. Integrate and customize engine modules for multiplayer environments, diagnose performance across hardware, collaborate with artists and designers, produce technical documentation, participate in code reviews, and contribute to agile development workflows.

Create and curate high-quality graphic design datasets and training materials for AI systems. Collaborate with engineers to evaluate and refine AI-generated visuals, document design processes and style guides, and translate design concepts into actionable training data. Stay current with design trends and communicate feedback to cross-functional teams.

Lead architecture and build large-scale, low-latency real-time data and streaming systems for a security platform. Design distributed streaming infrastructure with Apache Flink, write production Java and Rust code, optimize scalability and reliability, mentor engineers, and drive long-term technical strategy in collaboration with product and security stakeholders.

Evaluate AI-generated legal responses for accuracy and completeness, design prompts and scenarios to test legal reasoning, assess outputs against legal standards, provide actionable feedback, and support work across contracts, litigation, corporate law, regulatory analysis, compliance, and legal research.

Design realistic civil litigation scenarios, draft attorney-level gold-standard responses, evaluate and grade AI-generated legal outputs using structured rubrics, provide detailed written feedback, and participate in onboarding and calibration. Minimum 20 hours/week; remote work across US, Canada, or UK.

Lead architecture, development, and delivery of enterprise-scale real-time streaming solutions using Apache Flink and Java. Manage and mentor engineering teams, design fault-tolerant distributed systems, implement stream processing pipelines, and ensure performance, scalability, and production reliability. Collaborate with stakeholders across product, DevOps, and architecture to drive technical roadmaps and best practices.

Design and review consulting-style prompts, structured answers, and evaluation criteria to benchmark AI outputs against consulting frameworks. Provide structured feedback on clarity, logic, and business rigor. Conduct online research and synthesize insights to support evaluations and improve model alignment. Work remotely as an independent contractor on a flexible, part-time engagement.

Work with research teams to close mathematical knowledge gaps in LLMs by creating and evaluating advanced math problems and solutions, and providing clear written feedback to improve AI model performance. Remote, part-time independent contractor role (15-20 hrs/week) with potential extension.

Partner with research teams to design and evaluate complex, real-world operations tasks and solutions, provide actionable feedback, and improve LLM performance by contributing high-quality training and evaluation data.

Provide expert Vectorworks knowledge to inform and validate AI-driven design workflows: document file structuring, class/layer management, and iterative design processes; translate between Vectorworks, AutoCAD, and BIM; collaborate with AI teams, communicate design rationale, test AI outputs, and produce clear workflow documentation.