Top Tech Jobs & Startup Jobs in Chicago, IL

Supports treasury operations by analyzing payroll and transaction data, monitoring bank transactions, preparing and releasing payroll files, processing ACH requests, tracking funding limits, resolving payment issues, and generating reports on trends and anomalies. The role also assists customers and collaborates with banks and internal teams to ensure accurate, compliant, and timely financial processing.

Own the enterprise AI strategy, roadmap, governance, investment priorities, and measurement framework. Identify and prototype high-value AI use cases, guide pilots into production, establish responsible-AI standards for sensitive data, and communicate outcomes to executives. Build adoption through enablement and reusable practices while coordinating technology, business, legal, security, data, and vendor partners. Lead the emerging AI strategy function and hold teams accountable for delivery and value realization.

Builds and leads an in-house supplier recruitment and retention calling team for virtual card programs. Responsibilities include making supplier calls, developing scripts, recruiting and training callers, managing performance, tracking KPIs, improving conversion and save rates, reporting results, handling supplier assistance, and establishing workflows with the Payment Optimization and Operations team. The role begins hands-on and evolves toward coaching, performance management, staffing strategy, and program leadership.

Leads simple customer implementation projects under close supervision, supporting project plans, schedules, task tracking, documentation, status reporting, governance, risk escalation, and customer communication. The role also assists project managers and the PMO with administrative activities while learning OSV’s delivery methodology, platforms, and tools.

Leads tax notice resolution operations while maintaining an active caseload of complex federal, state, and local payroll tax issues. Provides technical guidance, manages queue priorities, researches filings and payments, coordinates with tax agencies and customers, supports quality assurance, and coaches specialists. Identifies recurring issues and process gaps, contributes to documentation and improvements, and ensures accurate, timely, compliant case resolution.

Processes client payroll settlements and on-demand payments in Workday, manages control reports and treasury exceptions, maintains support documentation, and provides customer-focused payroll service. The role requires strong organization, communication, mathematical, problem-solving, and time-management skills while handling multiple customers and tight deadlines.

Senior Database Administrator responsible for optimizing MySQL and AWS Aurora query performance, indexes, execution plans, stored procedures, and database architecture. Supports SQL Server and AWS RDS environments, cloud migrations, schema refactoring, data modeling, maintenance, backups, and operational tuning. Collaborates with developers and QA teams on database code reviews and mentors engineers on query optimization. The role requires extensive DBA experience, cloud database migration expertise, and strong relational data modeling skills.

Develop and maintain software using C#, .NET, web technologies, SQL Server, and AWS. Participate in the full SDLC and Agile Scrum processes, including design, development, unit testing, defect resolution, backlog refinement, and collaboration with product and QA teams. Build solutions using Microsoft-stack technologies, optimize databases and stored procedures, and support cloud-based application delivery.

Leads the platform and ecosystem product strategy for TaxEx, Treasury, and BPaaS solutions, expanding OSV beyond Workday. Owns product vision, discovery, roadmaps, commercialization, partner ecosystems, integrations, and market expansion. Builds relationships with payroll, HCM, ERP, processor, and channel partners while collaborating across engineering, operations, compliance, sales, and marketing. Establishes product governance, develops high-performing product teams, and drives adoption, recurring revenue, partner outcomes, and scalable platform capabilities.

The Procurement Director will design and implement procurement strategy, policies, and procedures; own the source-to-pay lifecycle; manage sourcing, RFPs, contracts, vendors, and onboarding; and lead cost-saving initiatives. The role establishes procurement workflows, systems, reporting, approval controls, and performance metrics while partnering with Legal, IT, and business leaders. It requires progressive procurement experience, strong negotiation and vendor management skills, analytical ability, and experience scaling a procurement function.