Top Tech Jobs & Startup Jobs in Chicago, IL

Operate, maintain, and improve secure, highly available server, network, and middleware infrastructure. Install, configure, monitor, troubleshoot, automate, and document systems; support on-call rotation and disaster recovery; manage job schedulers and vendor relationships; plan capacity and upgrades; mentor junior staff and support multi-cloud workloads.

Lead and mentor a distributed data engineering team while architecting and building a next-generation, largely open-source data platform. Own hands-on POCs, pipeline design, schema and query optimization, ETL reliability, observability, testing, and CI/CD. Evaluate and recommend technologies, drive migration from vendor lock-in, and translate advertising and market research needs into robust technical solutions.

Lead implementation of software safety programs for underwater robotic/autonomous vehicles per MIL-STD-882. Produce safety plans and assessments, perform hazard analyses, track coverage metrics, catalog safety artifacts, review software independently, and present findings at reviews and customer meetings. Coordinate across programs and support demanding schedules with occasional travel.

Lead design and implementation of scalable backend solutions, collaborate on requirements and specs, troubleshoot complex technical issues, conduct and lead code reviews, ensure rigorous automated testing, leverage AI tools to improve workflows, and support high-volume transactional processing.

Lead post-sales value realization by turning pre-sales ROI commitments into measurable outcomes. Build measurement frameworks, track KPIs, run executive value reviews, identify expansion signals, create reusable value playbooks, and feed outcome data into product and solution design to support renewals and growth.

The Global Head of Pricing will lead pricing functions, optimize margins, develop pricing models, and ensure accurate billing while partnering with multiple teams.

Provide litigation expertise to evaluate and improve AI-generated legal content. Review outputs for factual and legal accuracy, identify errors and inconsistencies, draft or edit sample legal language, and offer expert judgment on complex edge cases. Provide detailed written feedback and collaborate asynchronously with a cross-functional team to refine model behavior and professional standards.

Lead end-to-end M&A integrations as a hands-on project manager: build and run detailed plans, coordinate Finance/Operations/Systems/Talent, manage concurrent integrations, drive first-90-day outcomes, report to VP, support playbook improvements, and lead change management with operating company teams.

Partner with sales to gather customer requirements, design and demo Upshop SaaS retail solutions, scope SOWs, draft deliverables, lead discovery sessions, provide SME guidance, maintain demo environments, and hand off to project and customer success teams. Act as trusted advisor to executives, develop future-state roadmaps, reduce implementation risk, and support sales events and trade shows. Travel up to 30%.

Lead and develop a Strategic Account Management team to retain and grow largest SaaS customers. Drive account strategies, executive relationships, renewals, expansions, adoption, forecasting, and cross-functional collaboration to achieve retention (96%+), revenue targets, and increased platform adoption.