Top Tech Jobs & Startup Jobs in Chicago, IL

Own enterprise sales across Texas cities, municipalities, and public infrastructure agencies. Lead complex government sales cycles from prospecting through contracting, run outcome-based pilots, convert them into multi-year agreements, navigate RFP/RFQ and cooperative purchasing processes, build ROI cases, maintain stakeholder engagement, and grow pipeline through targeted outreach, industry conferences, and an existing public-sector network.

Leads global compensation and benefits programs, including salary structures, incentive plans, equity, benefits, open enrollment, 401(k), leave administration, compliance, audits, and payroll coordination. Owns HR metrics, systems, policies, process improvements, change management, and AI-in-HR strategy. Partners with leadership, vendors, payroll, IT, and external stakeholders to improve employee experience and operational efficiency.

Own end-to-end customer order fulfillment by coordinating vendors, logistics, and internal teams. Provide customer support, resolve issues and escalations, support onboarding, and strengthen customer satisfaction and retention. Collaborate cross-functionally with procurement, finance, product, engineering, and customer success teams. Monitor recurring issues, improve operational processes, and develop effective SOPs and workflows while managing multiple customers and orders.

Own and scale Zippy’s wholesale and broker revenue channels by setting growth strategy, managing channel performance, expanding markets, developing partner acquisition and activation playbooks, and optimizing revenue. Establish metrics, reporting, operating cadence, and accountability systems; guide resource allocation; oversee partner ecosystem health; and align Growth, Product, Originations, Capital Markets, and executives around scalable execution and risk management.

Engineering interns support analysis, testing, consulting, data collection, technical calculations, field work, inspections, and engineering evaluations. They collaborate with multidisciplinary teams, prepare technical reports and presentations, apply engineering principles to client challenges, and present project results to leadership. The program provides hands-on experience, mentorship, and exposure to aerospace, energy, industrial, manufacturing, infrastructure, and emerging technology projects.

Designs and maintains enterprise data integrations, metadata pipelines, APIs, workflows, data models, catalogs, and governance solutions. Resolves data quality and interoperability issues, documents technical processes, and collaborates with developers, data stewards, analysts, and governance stakeholders. Independently manages technical workstreams from requirements through implementation, testing, troubleshooting, and documentation. The role requires SQL, relational database, data modeling, cloud platform, API, and structured data experience, plus eligibility for a Secret clearance and DoD CAC.

Support cross-functional teams in planning, tracking, and coordinating programs. Prepare documentation, status reports, and dashboards; identify risks and dependencies; support meetings and process improvements. Remote, 3-month unpaid internship with possible extension or conversion.

Internship SRE role responsible for availability, performance, and scalability of an e-commerce supply-chain platform. Tasks include SLO/SLA definition, observability (Prometheus/Grafana/Loki/Tempo/OpenTelemetry), incident response, capacity planning, disaster recovery for PostgreSQL, infrastructure-as-code (Terraform), CI/CD automation, and operational reliability for AI agent services. Mentored by Head of Technology/CTO with potential conversion to full-time based on performance.

Lead and implement full-stack architectural foundations across frontend, backend, and AI interfaces. Define API-first patterns, select standardized libraries and monorepo practices, produce system diagrams and documentation, enforce code quality and testing, and mentor developers to improve performance, security, and maintainability.

Monitor NBA and WNBA news, lineups, and storylines; create engaging social media posts for Underdog’s basketball accounts; develop evergreen content ideas; integrate products, odds, and markets into social content; and support backend administrative systems. WOOF WOOF

The Content & Prompt Operations Specialist manages AI-assisted content workflows, ensuring accuracy and engagement in content produced. Responsibilities include writing prompts, drafting content, proofreading, and improving AI outputs while following structured processes.

Lead an IT software engineering and support team responsible for digital platform stability, defect resolution, incidents, and system enhancements. Prioritize requests based on business value, urgency, and feasibility; communicate trade-offs and timelines to stakeholders; establish support and ticketing processes; analyze defect trends; and drive continuous improvement. Champion team adoption of agentic AI coding tools, prompt and context engineering, reusable integrations, and evidence-based verification of AI-generated work.