Top Tech Jobs & Startup Jobs in Chicago, IL

Owns the vision, roadmap, and delivery of the Invoices & Payments product domain. Defines invoice generation, adjustments, payment allocation, refund, reconciliation, and correction workflows. Partners with engineering, FinOps, finance, operations, and customer service to translate complex requirements into scalable product capabilities, reduce manual intervention, improve payment matching, and support accurate, auditable financial outcomes.

Lead modernization of legacy .NET applications into cloud-native .NET services. Drive architecture, design scalable APIs, improve performance and resilience, embed observability and secure-by-default patterns, mentor engineers, and support high-severity incidents while collaborating with Infrastructure, Security, Data, and Operations teams.

Supports indirect and property tax compliance across multiple jurisdictions by preparing and reconciling tax reports, supporting filings and audits, researching notices, communicating with tax authorities, and resolving discrepancies. The role also manages tax calendars, documentation, payments, and recurring workflows while partnering with accounting, treasury, accounts payable, and operations teams.

Lead product strategy, roadmap development, and delivery for vehicle intake and assignment products serving insurance carriers and providers. Improve upstream user experiences, routing, cycle time, costs, and risk through prediction-driven solutions. Partner with Operations, Engineering, Data, Design, and business stakeholders; define requirements, business cases, KPIs, and priorities; research market trends and competitors; and represent carrier needs within Product Management.

Process and validate invoices, purchase orders, and expense reports; code invoices to the general ledger; input data into ERP; research and resolve unpaid invoices; print and distribute checks/vouchers; respond to vendor and staff inquiries; maintain AP records and follow-up on incomplete paperwork.

Lead modernization of legacy .NET applications into scalable, cloud-native services supporting auction, logistics, payments, titles, and yard operations. Design APIs and domain-oriented architectures, improve reliability and observability, establish engineering standards, implement secure application patterns, and mentor engineers. Collaborate with Product, Architecture, Infrastructure, Security, Data, and Operations teams on complex technical initiatives.

Supports sales compensation operations, including commission calculations, payout preparation, data validation, exception tracking, reporting, and stakeholder inquiries. Maintains compensation data, reports, documentation, and incentive compensation system updates. Assists with testing, plan administration, expense estimates, process improvements, and data-quality initiatives while escalating complex issues. The role requires accurate, timely execution across high-volume, time-sensitive compensation cycles.

Supports recurring sales compensation administration, including commission calculations, payout preparation, exception tracking, data validation, reporting, and ICM system updates. Maintains compensation data, documentation, dashboards, and standard procedures; researches stakeholder inquiries and escalates complex issues. Partners with Finance/FP&A on incentive expense estimates and supports testing, process improvements, and data quality initiatives during time-sensitive compensation cycles.

Design, develop, test, and maintain full‑stack web applications using the .NET stack. Build responsive UIs with ASP.NET MVC and React, implement backend services with .NET/.NET Core, write database queries for MS SQL Server and PostgreSQL, participate in code reviews, CI/CD, and troubleshoot application issues.

Process and audit vehicle sale settlements, remittances, expenses, payable vouchers, invoices, refunds, and payments exceeding $20 million daily. Reconcile accounts, monitor branch issues, resolve payable and system problems, support audits and multiple departments, assist customers and brokers, document procedures, and perform reporting, testing, research, and special projects. The role requires advanced Excel skills, strong communication, analytical ability, organization, and strict deadline management.