Top Tech Jobs & Startup Jobs in Chicago, IL

Evaluate AI model responses to business strategy and consulting problems, create high-quality prompts and model answers, provide detailed feedback, assess reasoning using structured frameworks, identify gaps, and collaborate with project teams as guidelines evolve.

Design, develop, evaluate, and refine machine learning models using Python. Manage training data with MongoDB, build preprocessing and data pipelines, tune hyperparameters, benchmark model performance, document experiments, and deliver data-driven insights. Collaborate remotely with cross-functional contributors and support deployment or operationalization of models in cloud or enterprise environments.

Part-time in-house counsel reviewing and redlining technology contracts to train and evaluate legal AI models. Responsibilities include simulated negotiations, assessing AI responses, creating evaluation frameworks, and collaborating with product and research teams. Requires at least three years of in-house technology transactions experience, particularly with MSAs, NDAs, ISDA agreements, and derivatives.

Evaluates AI-generated software code for correctness, quality, architecture, and debugging performance. Creates challenging coding problems, reference solutions, and test cases, then reviews model reasoning and provides detailed technical feedback to improve AI performance on real-world software engineering tasks.

Develop and refine machine learning models using Python, analyze datasets with MongoDB, and integrate preprocessing and data pipelines. Evaluate models, tune hyperparameters, benchmark performance, document experiments, and deliver data-driven recommendations. Collaborate remotely with cross-functional contributors to improve and operationalize machine learning solutions in cloud or enterprise environments.

Reviews written content and AI-generated responses for accuracy, clarity, grammar, coherence, completeness, and guideline adherence. Provides concise, constructive feedback, identifies subtle linguistic errors, documents findings using evaluation tools, and consistently applies evaluation criteria during a four-week remote contract sprint requiring at least 20 hours per week.

Provides expert input on IT strategy, systems architecture, infrastructure optimization, vendor management, security compliance, and technical team leadership. Reviews IT solutions, documentation, workflows, and processes, offering recommendations to improve implementation, risk mitigation, integration, and operational efficiency. Participates in structured discussions and written assignments supporting the development of AI tools for IT professionals.

Evaluate AI model outputs on data science, statistics, machine learning, experimentation, and quantitative reasoning problems. Create expert prompts, datasets, and reference solutions; identify statistical and methodological errors; and provide structured feedback to improve model performance. The role requires Python, machine learning, statistics, data analysis, experimentation, Pandas, and data modeling expertise.

IT Manager responsible for advising on IT strategy, systems architecture, infrastructure optimization, vendor management, security compliance, risk mitigation, and technical team leadership. The role involves reviewing IT solutions, documentation, workflows, and processes while providing written feedback and real-world expertise to support development of AI tools for IT professionals.

Evaluate and improve AI model responses involving financial modeling, valuation, investment analysis, capital markets, and due diligence. Create expert prompts and reference answers based on real deal experience, identify errors and unrealistic assumptions, and provide feedback to improve financial reasoning. The role is contract-based and remote, requiring strong finance expertise, Excel proficiency, and written English communication.