Top Tech Jobs & Startup Jobs in Chicago, IL

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.

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.

Independent sales contractor responsible for prospecting local businesses, booking meetings, presenting advertising opportunities on retail wellness kiosks, and closing contracts. The role offers remote flexibility, commission-based earnings, sales training, optional leads, and support from experienced representatives. Candidates should be self-motivated, proactive, results-driven, and comfortable with advertising, marketing, or media sales.

Performs advanced actuarial analysis of health insurance issues, rates, underwriting criteria, forecasts, variances, provider contracts, benefit designs, and financial performance. Supports all lines of business, product development, delivery systems, regulatory compliance, and cross-functional workgroups. Provides leadership and develops Actuarial Analysts while operating with minimal supervision.

Lead the evolution of Assured’s design system, defining shared patterns, standards, tools, and infrastructure across Design, Product, Brand, and Engineering. Improve craft, consistency, accessibility, and scalability while exploring AI-enabled design workflows. The role combines strategic leadership with hands-on product, interaction, and visual design work to enable teams to build high-quality experiences efficiently.