Top Tech Jobs & Startup Jobs in Chicago, IL

Supports go-to-market finance and analytics by building dashboards, analyzing pipeline and revenue performance, measuring account-based marketing effectiveness, and delivering financial models, forecasts, budgets, and business insights. Partners with Sales, Marketing, Revenue Operations, and Finance to standardize metrics, improve reporting, evaluate investments, and support planning and performance discussions.

Owns finance and analytics for the go-to-market organization, developing executive dashboards, forecasting models, financial frameworks, and ABM performance measurement. Partners with Sales, Marketing, Revenue Operations, Systems, and executives to guide planning, investment decisions, pipeline and revenue optimization. The role also establishes data governance, automates reporting, and builds and leads a high-performing analytics function.

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.

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.

Drive new business for MyChoice Accounts (consumer spending accounts) by selling to large employers (8,000+ lives). Build broker/partner relationships, manage full sales cycle, maintain pipeline and CRM records, present platform capabilities, attend industry events, and collaborate with sales support and marketing to exceed revenue targets.