Top Tech Jobs & Startup Jobs in Chicago, IL

Provide private equity expertise to evaluate and create high-quality financial and investment content for training AI systems. Review financial models, market analyses, deal documents, support due diligence, deal sourcing insights, and give structured feedback to improve analytical accuracy.

Build and maintain straightforward 2D game features using Java and libGDX to generate high-quality training data for AI. Implement basic mechanics (sprite management, game loops, input handling), fix performance issues, participate in code reviews, document workflows, and collaborate remotely with AI experts and cross-functional teams.

Develop and evaluate 2D game content in Solar2D, provide feedback on mechanics and level design, capture gameplay scenarios and edge cases, support gameplay data collection and annotation for AI training, and collaborate remotely to ensure accurate, consistent deliverables.

Participate in a one-month AI fellowship evaluating model outputs, simulating SaaS contract negotiations and redlines, assessing commercial contract risks, and providing structured feedback to improve AI training and legal workflows.

Drive net-new enterprise IT services revenue by owning full sales lifecycle: prospecting, executive engagement, solution positioning, collaboration with presales/delivery, pipeline management, and closing multi-year managed services, application modernization, and digital transformation deals to meet $5M–$10M annual targets.

Transcribe Assamese video content with timestamps, analyze speaker tone and intent, evaluate grammar and idioms, perform semantic and contextual analysis, collaborate to improve processes, and maintain confidentiality and accuracy.

Provide advanced M&A financial modeling, valuation (DCF, comparables, precedent transactions), and transaction analysis to support deal structuring, due diligence, and strategic recommendations. Quantify synergies, test assumptions, build integrated operating models, and present findings to senior stakeholders in a remote contract role.

Apply deep management consulting and corporate strategy expertise to improve generative AI LLMs: identify knowledge gaps, create annotation standards and evaluation rubrics, review consulting tasks, provide feedback, and collaborate with research teams to boost model reasoning and performance.

Serve as the internal customer advocate and pre-sales technical lead for finance-focused enterprise deals. Configure complex billing, pricing, metering, invoicing, and revenue recognition workflows; build demo environments; engage finance leaders; support RFPs and sandbox configurations; document solutions and handoffs; feed product and engineering with customer insights.

Remote Autodesk Inventor expert role to create and refine 3D models, assemblies, and technical drawings; collaborate with cross-functional teams, solve design issues, ensure manufacturing compliance, lead design reviews, and mentor junior designers.