Top Tech Jobs & Startup Jobs in Chicago, IL

Lead and mentor a cross-functional Product Engineering team (frontend and backend), drive architecture and technical direction, collaborate with product/analytics/design, remove blockers, iterate on agile processes, and ensure code quality, testing, and scalable system design.

Lead national engagement with district Chief Academic Officers, developing strategy, convenings, trainings, and tools that translate College Board research and data into district-facing guidance. Build partnerships, represent College Board externally, manage and coach the Evidence-based Learning and Leadership team, and ensure alignment with organizational strategy and goals.

Design and prototype LLM- and agent-based workflows (RAG, tool-calling), build reusable connectors and agent templates, integrate data science models, define clean API boundaries, implement lightweight evaluation/logging, and collaborate with data science and leadership to operationalize AI systems.

Lead and deliver cross-team technical programs for 2-3 engineering teams. Serve as Scrum Master, run Agile ceremonies, track execution, manage risks and dependencies, improve SDLC and delivery processes, and communicate progress to stakeholders and leadership.

Process and verify invoices, expense reports, credit card charges, and payment requests; manage vendor records and inquiries; support month‑end/year‑end closings and AP continuous improvement initiatives.

Support and build Jira automations, administer core business systems, monitor Workato integrations, troubleshoot sync errors, manage user access and provisioning, generate reports, and document processes to improve system efficiency and data integrity.

Execute workflow-based test cases, report and track defects, collaborate with development to verify fixes, support releases, and ensure software quality for mortgage origination applications.

Support actuarial financial analysis, pricing, reserving, budgeting and forecasting. Develop probability tables, analyze premiums and liabilities, assist with M&A analysis, and generate statistical reports to estimate outcomes and inform decision-making.

Drive Brookhaven user acquisition and discovery on Roblox through creative testing, thumbnail/page experiments, and event-driven updates. Collaborate with product, creative, social, and creator teams to scale winning creatives, maintain experimentation cadence, build dashboards, and document playbooks to improve CTR and conversion.

Coordinate and manage concurrent IT onboarding and integration projects for new medical practices, including hardware installs, interface implementations (HL7), legacy data migrations, vendor coordination, stakeholder communication, training, process improvements, risk escalation, and ensuring HIPAA compliance.