Top Tech Jobs & Startup Jobs in Chicago, IL

Owns product vision, strategy, roadmap, requirements, prioritization, and lifecycle execution. Partners with directors, product owners, IT, implementation, and development teams to deliver solutions aligned with corporate goals. Conducts market and customer research, manages initiatives and release plans, influences stakeholders, and communicates product direction and user feedback within an Agile environment.

Oversee payroll tax operations, supervise specialists, ensure accurate federal and state tax filings, manage reconciliations and liabilities, interpret tax regulations, support audits, and improve accounting processes. The role also manages employer registrations, workers’ compensation reconciliations, budget projections, year-end reporting, quality reviews, and staff development while maintaining compliance and confidentiality.

Leads full-cycle recruiting for corporate and client-facing roles, including sourcing, screening, interview coordination, candidate evaluation, offers, and onboarding handoff. Partners with hiring leaders to develop recruiting plans, build talent pipelines, analyze recruiting metrics, create structured interview materials, and support inclusive candidate experiences. Organizes large-scale hiring events and travels up to 25% to support recruitment efforts.

Oversee client contracts and programs, ensuring compliance, operational excellence, and high-quality service delivery. Lead Client Engagement Managers and Specialists, establish performance goals, allocate resources, support growth, and improve processes. Partner with Operations, Product, Finance, Technology, and Project Management teams to align delivery with strategic initiatives. Monitor KPIs, analyze program data, resolve client issues, and provide recommendations to leadership.

Processes biweekly and semi-monthly payroll, including adjustments, garnishments, tax levies, ACH uploads, off-cycle payroll, and check distribution. Investigates payroll issues, follows up on missing or incorrect data, supports audits, safeguards HIPAA-protected information, and prepares reports. Requires strong Microsoft Excel, mathematical, organizational, analytical, communication, and multitasking skills.

Identifies and develops growth opportunities in self-directed Medicaid, LTSS, managed care, and related markets. Responsibilities include market intelligence, partnership development, opportunity qualification, full-cycle sales, pipeline management, proposal development, pricing and contract negotiation, executive reporting, and cross-functional coordination. The role requires expertise in Medicaid waivers, MCO contracting, government procurement, self-direction models, and CRM execution. This is a remote position with representation at select conferences and policy forums.

The Quality Assurance Tester II designs and executes test plans, leads regression testing, manages defects, and maintains automated UI and API test suites. The role collaborates with development and product teams in Agile ceremonies, analyzes test results, improves QA processes, and mentors junior testers. Responsibilities include front-end, back-end, database, load, and mobile application testing.