Top Tech Jobs & Startup Jobs in Chicago, IL

Provides frontline IT help desk support by diagnosing and resolving hardware, software, network, account, VPN, printer, and endpoint issues. Installs and configures systems, manages user accounts and permissions, documents solutions, monitors IT systems, follows security procedures, and escalates complex problems. Supports upgrades, deployments, network expansions, and users through phone, email, and ticketing systems while meeting service-level expectations.

Leads the end-to-end development of an AI-enabled revenue cycle management platform, spanning frontend, backend services, APIs, event-driven workflows, data models, and AI agent orchestration. Partners with users, product, operations, and business leaders to deliver measurable outcomes. Sets technical direction, mentors engineers, promotes AI-assisted development, and ensures secure, reliable, HIPAA-compliant software through strong testing and monitoring.

Develop fraud detection models and predictive features for account opening, account takeover, and identity risk. Responsibilities include investigating large datasets, identifying fraud patterns, engineering features, training and evaluating machine learning models, writing tested Python and PySpark code, supporting production deployment, monitoring model performance and drift, and presenting analytical recommendations. The role also requires adherence to data privacy, explainability, model validation, documentation, and governance standards.

Own end-to-end product design for web platform features, leading user research with educators and students, translating insights into accessible interfaces, prototypes, specifications, and engineering handoffs. Collaborate with designers and engineers, maintain the component library, and create AI-enabled experiences for educators and learners. The role is fully remote and emphasizes independent ownership, communication, human-centered design, and accessibility.

Identifies and approaches potential advertisers for Brythos Africa magazine, presents advertising opportunities, negotiates and closes sales, books advertising space, follows up on content, documentation, and payments, maintains accurate sales records, develops client relationships, and meets revenue targets. This is a flexible, field-based and remote commission opportunity with no fixed salary.

Leads cyber-market business development and federal capture activities across DoD and military service customers. Builds customer relationships, executes call and capture plans, validates requirements, develops winning strategies, leads proposal activities, and coordinates account leads, project managers, SMEs, and industry partners. Requires extensive federal cyber-market relationships, success winning large opportunities, acquisition-process expertise, and understanding of cyberspace doctrine and federal IT modernization.

Configure, optimize, and support UKG Pro WFM scheduling and clinical scheduling extensions. Partner with HR, operations, payroll, and IT to improve staffing, ensure labor and healthcare compliance, maintain data accuracy, troubleshoot issues, support upgrades, develop training materials, and provide workforce analytics for staffing decisions.

Resolves complex Tier 2 IT escalations across network infrastructure, telephony, endpoints, medical devices, and enterprise applications. Administers Google Workspace, Meraki, 8x8, and endpoint systems; coordinates procurement and field vendors; engineers chatbot workflows; supports healthcare go-lives; and mentors Tier 1 technicians. Develops documentation and process improvements while providing autonomous remote support in a healthcare environment.

Supports UX research throughout the product lifecycle by assisting with usability tests, interviews, surveys, diary studies, participant recruitment, data collection, analysis, and research documentation. Collaborates with designers, product managers, and developers to translate findings into actionable recommendations. The role also involves creating personas, journey maps, and presentations while applying accessibility and inclusive design principles.

Administers and secures Oracle databases supporting DISA contract systems. Responsibilities include database installation, tuning, access management, outage response, disaster recovery, security patching, STIG compliance, scripting, release support, data modeling, legacy data migration, reconciliation, and system integration. The role also supports Appian data stores and coordinates database changes with DISA, hosting providers, ISSOs, and development teams.