Top Tech Jobs & Startup Jobs in Chicago, IL

Processes complex employee benefits cases, including appeals, QMCSO orders, Medicare L-564 forms, POA requests, condolences, eligibility updates, and claims. Ensures compliance with HIPAA, IRS, and CMS requirements, protects sensitive data, resolves documentation issues, manages escalations, prepares reports, supports members and partners, and mentors junior staff while contributing to process improvements.

Supports accurate and compliant U.S. payroll processing, including biweekly payroll, timekeeping and employee-change validation, tax withholding, multi-state compliance, terminations, reconciliations, audits, reporting, year-end activities, and off-cycle payroll runs. Investigates discrepancies, responds to employee payroll inquiries, maintains confidential records, and provides backup support during absences or high-volume periods.

Lead end-to-end UX for web and mobile products: create wireframes, prototypes, and high-fidelity designs; run user research and usability testing; maintain design systems; use data to drive decisions; collaborate with PMs and developers; and mentor junior designers to improve product experiences.

Lead end-to-end payroll data integration implementations during client onboarding. Gather requirements from clients and payroll vendors, configure and test inbound and outbound payroll files, document file layouts and mappings, manage risks and timelines across multiple projects, and coordinate quality assurance, defect resolution, and handoff to ongoing operations. Serve as the primary implementation contact while delivering clear communication and technical documentation.

Owns defined product features and workflows from discovery through launch and post-launch improvement. Creates product artifacts, partners with engineering and design, uses customer feedback and analytics to prioritize work, prepares launch plans, monitors adoption and quality, and maintains roadmap and backlog hygiene. The role also develops expertise in benefits administration, SaaS, compliance constraints, and cross-functional product delivery.

Manages client onboarding implementation projects from planning through completion. Responsibilities include defining objectives, schedules, milestones, risks, dependencies, budgets, and success criteria; coordinating clients, executives, vendors, and cross-functional teams; allocating capacity and resolving conflicts and bottlenecks; tracking progress; and driving continuous process improvement. The role requires managing multiple complex projects simultaneously while ensuring timely, high-quality, and cost-effective delivery.

Configure and validate benefits system builds, review and QA data, follow enrollment and implementation process flows, document processes, collaborate with internal partners, track productivity, escalate issues, and participate in training on new functionality.

Lead development and adoption of AI-driven and traditional test automation, maintain UI automation frameworks, own performance/load testing strategy, align testing to architecture and risk, mentor QA engineers, and collaborate with product and engineering to improve quality and testing efficiency.

Serve as the strategic lead for 1-2 national brokerage firms to design partner-aligned solutions, drive broker-influenced pipeline, support high-priority deals, coordinate cross-functional teams, and surface broker-driven product and packaging feedback to influence roadmap and go-to-market.

Design, build, test, and deploy production software for an agentic chatbot platform across intake, orchestration, retrieval, answer generation, caching, and integrations. Collaborate with product and technical teams, provide code and merge-request review, mentor junior engineers, and contribute to design, performance, security, and delivery.