Top Tech Jobs & Startup Jobs in Chicago, IL

Processes client payroll settlements and on-demand payments in Workday, maintains support documentation, manages daily control reports, and resolves Treasury exceptions. The role requires strong organization, communication, customer service, mathematical, and problem-solving skills while supporting multiple clients and meeting tight deadlines. It is an entry-level opportunity with no supervisory responsibilities and focuses on accurate, confidential payroll processing.

Provides end-to-end payroll processing support for multiple managed customers, including case management, escalations, root cause analysis, client calls, Workday payroll configuration, year-end processing, tax and audit troubleshooting, compliance support, and customer issue resolution. Maintains documentation, meets service metrics, and collaborates with internal and customer teams in a remote environment.

Provides advanced escalation support for complex enterprise application incidents. Performs technical analysis across applications, batch processing, databases, integrations, access, performance, reporting, and APIs. Leads technical communication during critical incidents, develops workarounds, supports root cause analysis, documents resolutions, evaluates software release impacts, and coordinates with development, engineering, DevOps, and vendors. Requires enterprise application support experience, SQL and API troubleshooting skills, payroll tax expertise, and knowledge of incident management and system architecture.

Manage COBRA and direct billing operations, including case updates, client onboarding and offboarding, elections and payments, plan and rate changes, carrier communications, HR system submissions, audit requests, and integration-file corrections. The role requires employee benefits and COBRA regulatory knowledge, strong analytical and communication skills, confidentiality, process-improvement participation, and independent work in a fast-paced environment.

Lead end-to-end payroll tax implementations from discovery through go-live. Act as primary tax expert, configure tax systems, validate and load data, reconcile historical records, coordinate cross-functional teams, advise customers on configuration decisions, and help improve methodologies and training materials.

Serve as Product Owner for Payroll Tax (TaxEx) product: gather and translate business and technical requirements, manage backlog, support Agile ceremonies, design solutions, assist QA/user testing/training, and document processes for payroll tax imports, remittances, filings, and workflows.

Serve as the organization's internal payroll tax authority: advise product, sales, and implementation on complex multi-jurisdictional tax configurations, resolve escalated technical/tax issues, contribute to product roadmap and UAT, and convert deep tax knowledge into training, guides, and customer-facing advisory work to scale team expertise.

Researches, analyzes, and improves payroll tax processes; performs audits, reconciliations, and escalations using TaxEx, Workday, and Atmos; responds to agency notices; develops SOPs, process maps, and supports tax-related projects and system testing.

Serve as the primary technical operations liaison for payroll tax implementations and production support. Validate and troubleshoot data files and integrations (XML/CSV/TXT/JSON), manage escalations, coordinate testing and cutovers, ensure data quality, advise on tax setup, and document SOPs to support customer onboarding and daily operations.

Maintain and update tax profile data for OSV customers, manage customer cases, analyze payroll tax data, meet reporting deadlines, and collaborate with internal teams to ensure accurate payments and filings.