Top Tech Jobs & Startup Jobs in Chicago, IL

Design task-specific, objective evaluation frameworks for data science deliverables. Assess AI- and human-generated analyses, models, dashboards, experiments, and recommendations using reproducible scoring. Produce detailed written justifications, refine methodologies with reviewer feedback, and collaborate with cross-functional teams to improve AI training and evaluation standards.

Use Spanish voice commands to perform everyday tasks, record and correct transcripts, evaluate AI responses for accuracy and naturalness, maintain logs, upload recordings, and follow quality standards to improve multilingual voice AI systems.

Seeking an Engineering Manager or Principal Engineer to drive technical advancement. Must have extensive Java, Apache Flink, and Rust experience, strong background building scalable distributed systems, proven leadership, and a high-ownership, builder mindset in a security-focused company.

Serve as the internal customer advocate and technical pre-sales lead for finance-heavy billing and revenue recognition solutions. Translate complex billing and revenue requirements into configured demos, sandbox environments, and solution documents. Partner with Sales, Product, and Engineering to support discovery, RFPs, implementations, and handoffs for enterprise customers.

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.

Lead budgeting, forecasting, and variance analysis while building AI-driven financial models, scenario planning, KPIs, and dashboards. Automate FP&A processes, deliver insights to senior leaders, and collaborate with cross-functional teams to improve forecast accuracy and strategic decision-making.

Provide clinical expertise to improve AI mental-health tools: annotate clinical interactions, evaluate psychotherapy datasets, design psychological testing scenarios, apply CBT frameworks, collaborate with engineers, ensure ethical standards, and drive research-backed AI improvements.

Serve as a domain expert in electrical engineering to identify and close knowledge gaps in LLMs. Collaborate with research teams to design and evaluate complex problems, provide detailed written feedback, and improve AI model performance. Remote, contractor role with weekly pay and flexible hours.

Provide real-world financial planning expertise to train and evaluate AI systems. Review scenarios, assess AI recommendations for accuracy, compliance, and suitability, document client conversations, define planning methodologies, give structured feedback, identify compliance/referral needs, and improve AI workflows and financial planning processes.

Design, implement, and optimize AI-driven solutions across the claims lifecycle (intake, investigation, adjudication). Build ML models for data extraction, fraud detection, reserve setting, subrogation, and adjudication decision engines. Collaborate with underwriting, fraud, legal, and IT to integrate models into operations and improve efficiency, accuracy, and compliance.