Top Tech Jobs & Startup Jobs in Chicago, IL

The Senior UX/UI Designer will own design features at Syllo, collaborating closely with design, product, and engineering teams to deliver polished user experiences, managing design systems and iterating efficiently.

The Staff Engineer will lead the Systems team, design scalable cloud infrastructure, optimize data pipelines, and ensure platform reliability and security.

The Engineering Manager will mentor a team of engineers, improve processes, collaborate with product managers, and define staffing strategies.

Lead operational execution for Product & Engineering: drive day-to-day SDLC, manage work from triage to completion, maintain GitHub Projects as source of truth, coordinate cross-functional teams, remove blockers, and improve engineering processes and delivery predictability.

Own and organize the product documentation library; author internal and client-facing documentation across the litigation lifecycle; produce procedural guides, decision trees, and visual workflow diagrams; write quick-turn responses to client questions; edit and polish release notes and translate developer updates into client-centric value propositions.

Lead design and implementation of a production inference platform for LLMs. Define roadmap, integrate and optimize inference runtimes, manage GPU infrastructure, and build systems for deployment, autoscaling, observability, and operational excellence. Benchmark models/runtimes, partner with ML and product teams, make architectural tradeoffs, and mentor engineers to scale AI infrastructure.

Lead and own Syllo's QA strategy, build scalable automated testing frameworks integrated into CI/CD, and drive quality across Engineering, Product, and Customer Success. Champion QA processes, measure and improve release standards, reproduce and validate complex customer issues, and leverage AI/LLM tools to modernize test generation, failure analysis, and automation to increase release confidence and reduce manual testing.

Serve as first point of contact for clients, troubleshoot product and technical issues, conduct live walkthroughs, write help content, document solutions, escalate recurring issues to product/engineering, and participate in product testing.

The Senior Content Specialist will create high-quality external and internal marketing collateral, manage the content lifecycle, and collaborate with executives to evolve brand messaging.

Support the Head of Finance with accounting schedules, depreciation/amortization, variable compensation, invoicing, AR/AP, payroll, financial filings, month-end close, budgeting, cap table and board prep. Perform financial analysis in Excel, provide administrative support to senior leaders, handle sensitive information discreetly, and identify workflow improvements. Assist with audits, collections, and ad hoc finance and operations tasks.