Top Tech Jobs & Startup Jobs in Chicago, IL

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Lead Recruiter sources, screens, and hires healthcare professionals using job boards, social media, and ATS. Partners with hiring managers, schedules interviews, negotiates offers, manages onboarding, maintains candidate records, and represents the company at recruitment events to expand the talent pipeline.

Build and lead FamilyWell Health’s People function as its first full-time People leader. Responsibilities include HR infrastructure and HRIS, multi-state compliance, compensation and benefits, recruiting processes, workforce planning, performance management, employee relations, culture, and executive advising. The role supports a rapidly scaling mixed W-2 and 1099 workforce across clinical and corporate functions.

Designs, builds, tests, deploys, and supports full-stack features for a healthcare Registry platform. Responsibilities include frontend and backend development, PostgreSQL schemas and queries, REST APIs, webhooks, third-party integrations, observability, CI/CD, production troubleshooting, and HIPAA-compliant handling of PHI. The engineer collaborates with Product, Data, and Clinical Operations in a remote startup environment.

Own end-to-end acquisition of net-new B2B trade and hospitality accounts, including prospecting, pitching, closing, pipeline management, and relationship development. Build repeatable AI-powered outreach workflows, maintain CRM discipline, improve forecasting and conversion, and coordinate with merchandising, operations, and vendor teams to support trade clients and special orders.

Volunteer WordPress Developer to migrate and maintain a content library, build new features, and create custom themes, plugins, and widgets. Work remotely for ~5+ hours/week, attend weekly meetings, and respond within 24 hours to support an active nonprofit volunteer team.

Execute B2B demand-generation campaigns: build and optimize paid search and paid social, create LinkedIn audiences, perform keyword research, report pipeline metrics, prepare QBR decks, and collaborate on quarterly client plans.

Design and build interfaces for HUD’s AI agent training, evaluation, and marketplace products. Translate complex reinforcement learning workflows, agent runs, evaluation results, reward signals, and quality feedback into clear, actionable experiences. Collaborate with users, researchers, and engineers to ship polished products, conduct user discovery, improve usability, and develop reusable interaction patterns.

Own the HUD data marketplace product lifecycle, improving vendor onboarding, submission workflows, quality feedback, and marketplace management. Enable research teams to discover, evaluate, and access AI training data and RL environments. Partner with engineering, research, GTM, and operations to simplify complex workflows, define marketplace health metrics, and prioritize product improvements using user feedback and quantitative data.

Lead research on improving AI agent training data and evaluations. Manage and mentor research engineers, define research direction, design rigorous experiments, validate data quality, diagnose reward and grading failures, and translate findings into scalable tools, workflows, and standards. Collaborate with engineers, domain experts, and vendors while communicating technical conclusions and tradeoffs clearly.

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.

Supports and optimizes indirect procurement operations through Coupa administration, P2P workflow execution, supplier onboarding, approval routing, invoice processing, reporting, governance, and audit readiness. The role improves workflows, catalogs, automation, data visibility, and user adoption; resolves system and transaction issues; supports Coupa implementations and UAT; trains users; and partners with Procurement, Finance, Legal, Accounts Payable, IT, and business stakeholders.

Build web-first product experiences, reusable components, RESTful APIs, and scalable data pipelines for Wikimedia’s web and mobile app surfaces. Deliver initiatives from discovery through production, emphasizing accessibility, performance, testing, observability, and maintainability. Collaborate with product managers, designers, analysts, and native app engineers in a fully remote environment while prioritizing user impact, technical quality, and pragmatic delivery.

Build and improve scalable, accessible iOS experiences for Wikipedia. Lead technical discovery, system design, implementation, testing, observability, prioritization, and delivery of medium-complexity initiatives. Collaborate with product managers, designers, analysts, and engineers while managing scope, risks, tradeoffs, and documentation. The role requires strong Swift, SwiftUI, UIKit, iOS architecture, and performance optimization experience in an autonomous, remote, cross-functional environment.