Top Tech Jobs & Startup Jobs in Chicago, IL

The Payroll Support Advisor provides technical and payroll processing support, addresses inquiries, performs root cause analysis, and seeks solutions to enhance service quality.

Provide advanced technical and payroll processing support, troubleshoot complex payroll/system issues, perform root cause analysis, ensure compliance with payroll laws, drive continuous improvement, analyze casework to identify trends, support onboarding and enterprise projects, and act as a payroll subject matter expert for internal and external stakeholders.

Design and execute test scenarios for payroll tax compliance changes, validate tax calculations and outputs, document test results, manage defect lifecycle, collaborate with Compliance and Development to resolve issues, maintain test documentation and scenario libraries, and contribute to testing process improvements.

The Sr. Quality Assurance Automation Engineer creates and executes automated tests and maintains regression suites for multiple products, ensuring high-quality releases.

Ensure accurate, timely wage garnishment processing by reviewing and setting up garnishment orders, maintaining payroll garnishment rules, generating reports, resolving automation failures, responding to courts/agencies/employees, processing lump-sum withholdings, and performing reconciliations and related special projects.

The VP of Technology Operations oversees operational discipline, quality culture, incident management, and technology planning across engineering to ensure process continuity and performance.

Monitor federal, state, and local tax agencies for payroll-related regulatory changes; research and interpret routine requirements; document authoritative guidance and data needs; create clear change requests for downstream teams; maintain agency relationships and audit-ready records; communicate updates to stakeholders and support process improvement initiatives.

Lead and develop a team of Tax Account Managers to deliver tax service bureau operations, manage escalations, ensure compliance, maintain customer relationships, track KPIs, use Workday/OSV platforms, and drive process improvements and strategic initiatives.

The Sr. COBRA Specialist manages operational duties related to COBRA and Direct Billing, ensuring timely responses and updates while identifying process improvements and maintaining communication with internal teams.

The National Sales Director at OSV will lead channel sales for a SaaS offering, building relationships and closing deals to drive revenue growth.