Top Tech Jobs & Startup Jobs in Chicago, IL

Contract corporate income tax specialist to prepare ASC 740 provisions, corporate tax returns, transfer pricing documentation, and transaction tax analyses (GILTI, FDII, BEAT, Pillar Two, Section 163(j), FIN 48). Produce well-documented workpapers, tax positions, and recommendations for mock real-world exercises. Remote, contractor role with practical exercises for assessment.

Evaluate and improve AI-generated fund-related legal work by drafting, reviewing, negotiating, and redlining fund documents; develop evaluation frameworks and scoring rubrics; collaborate with product, research, and engineering teams to refine AI training data and legal guidelines; identify contractual risks and provide expert legal feedback.

Part-time contractor M&A attorney to draft, review, negotiate, and redline transaction documents; evaluate AI-generated legal outputs; develop evaluation frameworks and scoring rubrics; provide subject-matter expertise to improve AI training data and legal analysis; collaborate with product, research, and engineering teams to refine legal guidelines and best practices.

Part-time contractor role evaluating and training AI for contract review. Draft, review, negotiate, and redline commercial technology agreements; assess AI-generated contract responses; develop evaluation criteria and scoring rubrics; collaborate with product, research, and engineering teams to improve AI legal workflows and identify contractual risks.

Create high-quality motion graphics, animations, and visual effects using Adobe After Effects. Collaborate with creative teams to produce digital content, edit and composite video, optimize project files for multiple outputs, and troubleshoot rendering issues while maintaining brand consistency and meeting deadlines.

Review, validate, and annotate logistics documents (packing lists, bills of lading, inventory registers), evaluate supply chain workflows, recommend process improvements, provide structured feedback for AI training datasets, collaborate with cross-functional teams, and contribute to documentation and training resources to improve logistics operations.

Translate design specs into pixel-perfect, responsive web interfaces using TypeScript, CSS3, and HTML. Follow design systems and accessibility (WCAG) standards, optimize frontend performance, resolve spec ambiguities, collaborate remotely via documentation and code reviews, and provide frontend expertise to support AI model evaluation.

Design reproducible coding environments and high-quality reference solutions to train AI. Create and validate complex programming challenges, debug and optimize codebases, refactor legacy systems, document technical decisions, and review technical submissions while collaborating remotely.

Lead end-to-end recruitment marketing campaigns: plan and execute paid and organic content, manage content pipelines and calendars, measure campaign performance across channels, generate optimization insights, and coordinate with recruiters and stakeholders to improve candidate attraction and conversion.