Top Tech Jobs & Startup Jobs in Chicago, IL

Provide accurate Laotian<>English medical and legal interpretation remotely, including simultaneous and consecutive modes, using appropriate medical terminology, cultural mediation, VRI or scheduled appointments, and maintaining professionalism and confidentiality.

Lead and scale payroll implementation and operations for agricultural customers, ensuring accurate, compliant, and on-time payroll. Hire and manage payroll team, resolve payroll errors, advise on payroll and tax compliance, partner with Product and Sales, and drive process improvements to increase efficiency and customer satisfaction.

Temporary 4–6 month role supporting corporate and regulatory legal work for a multi-state cannabis company. Responsibilities include entity formation and management, M&A due diligence support, contract review and negotiation, state regulatory filings, corporate governance, legal research, and assisting senior attorneys. Opportunity to gain cannabis regulatory and transactional experience.

Senior Test Engineer responsible for designing and executing functional, regression, integration, and API tests for C#/.NET web and enterprise applications. Build and integrate automated Selenium and C# API tests into Azure DevOps CI/CD pipelines, track defects, and support manual testing (exploratory, UAT) while collaborating with Agile teams to ensure high-quality delivery.

Senior individual contributor who designs, develops, optimizes, and maintains complex SQL data solutions and Microsoft SQL Server instances. Leads data modeling, performance tuning, schema design, and data quality efforts; partners with engineering, ETL, BI, and product teams; drives standards, architecture, governance, and compliance for scalable, high-performance data platforms.

ProPublica’s Emerging Reporters Program awards five students $9,000 stipends, mentors, and a paid conference trip. Open to undergraduate juniors or seniors who demonstrate financial need and commitment to journalism. Runs late September–June with two stipend payments. Participants must be U.S. citizens or residents able to file taxes and provide a W-9 (SSN or ITIN). Mentors are matched by interest; conference expenses are covered. Program emphasizes diversity and inclusion.

Build, train, and evaluate machine learning models; prototype end-to-end solutions; produce analyses, dashboards, and visualizations; document processes; collaborate with product, engineering, and cross-functional teams to productionize models and support data-driven decisions.

Underwrite SBA 7(a), 504, USDA, and conventional commercial loans by analyzing financial statements, cash flow, collateral, and third-party reports; prepare credit approvals and memoranda; partner with BD, loan closing, and senior credit officers; ensure regulatory compliance and improve underwriting workflows, including thoughtful use of AI to accelerate analysis.

Lead strategy, roadmap, and execution for Treering Yearbooks. Use data, research, and cross-functional collaboration to improve activation, engagement, retention, and revenue. Define metrics, run experiments, build dashboards, and translate customer insights into product requirements. Guide discovery through launch and ensure stakeholder alignment and measurable outcomes.

Own the ecommerce and data product roadmap to grow acquisition, conversion, monetization, and retention. Use experimentation, analytics, customer research, and AI-driven features to optimize the search-to-purchase journey. Define KPIs, prioritize initiatives, run experiments, partner cross-functionally, and present results and strategy to executive leadership.