Top Tech Jobs & Startup Jobs in Chicago, IL

Work directly with customers to design, deploy, and integrate end-to-end AI evaluation pipelines. Curate data, define annotation schemes, set up LLM-based judges, run initial experiments, produce actionable results, and translate technical systems into practical workflows for users.

Provides Tier 2 technical support for Optain’s robotic retinal camera and software platform. Troubleshoots hardware, software, image quality, connectivity, EHR integration, and clinical workflow issues; handles medical device complaints under regulated quality processes; creates support documentation and training; improves internal tools and workflows; analyzes issue trends; and coordinates product, engineering, quality, regulatory, and customer success initiatives.

Build and manage sales pipeline through MSP events, conferences, roadshow dinners, field events, and high-volume outbound calls, emails, and LinkedIn outreach. Follow up with prospects, convert event conversations into qualified meetings, collaborate with Account Executives to improve messaging and handoffs, and maintain organized activity tracking. The role requires event confidence, strong communication, persistence, competitiveness, resourcefulness, and 1–2 years of BDR, SDR, or outbound sales experience, ideally in SaaS or cybersecurity.

Lead U.S. sales strategy and customer development for technical food ingredient and sweetener products. Responsibilities include prospecting, market research, technical presentations, proposals, sales negotiations, relationship management, forecasting, CRM administration, trade show participation, customer support, product feedback, and meeting revenue targets. The role requires close collaboration with internal stakeholders and customers, technical knowledge of sweetener formulation, market analysis, and travel of at least 50%.

Visit cafes across an assigned city and assess their work-friendliness for travelers. Verify WiFi quality, internet speed, passwords, outlets, seating, ambience, and other details, then submit accurate information through a digital survey. Plan visits across neighborhood clusters, work independently, and maintain high data quality and consistency. The role is suited to college students or people with flexible part-time schedules who are reliable, proactive, detail-oriented, and comfortable traveling independently within their city.

Design, develop, and maintain core database features for VillageSQL Cloud, emphasizing performance, stability, scalability, security, and reliability. Build distributed systems using Go and Kubernetes, collaborate on technical vision and architecture, contribute to open-source projects, participate in code reviews, troubleshoot complex issues, and engage with the developer community. The role focuses on database-as-a-service infrastructure and cloud service evolution.

Work with the development team to build and debug web applications: write Python backend code, create responsive HTML/CSS/JavaScript frontends, integrate frontend and backend, participate in code reviews and testing, learn frameworks and document progress.

Contract 2D Art Generalist creating concept art, illustrations, and character art for a surreal roguelike. Collaborate with the team to produce stylized, memorable visuals, iterate on art direction, and integrate assets into the game.

LOOKOUT News seeks freelance journalists, writers, and photographers to pitch articles focusing on solutions journalism and accountability reporting, especially around LGBTQ+ and underreported communities.

The Senior Product Manager will lead integration strategies for CEXs and Web3 Wallets, drive operational efficiency, and collaborate with engineering and business development teams to enhance core infrastructure and connectivity.