Top Tech Jobs & Startup Jobs in Chicago, IL

The Sr. Quality Engineer leads QA testing teams, implements QA strategies, monitors quality assurance processes, and collaborates across teams to enhance product quality and testing efficiency.

Senior Cloud Security Engineer responsible for hands-on remediation of cloud and infrastructure vulnerabilities, operating vulnerability and CSPM tooling, enforcing secure configurations across Azure environments, embedding security in CI/CD and IaC, supporting compliance/audits and reporting, mentoring engineers, and partnering with cross-functional teams to maintain cloud security posture and policy.

Owns strategy, governance, and execution of knowledge content across Intercom, NICE CXone Expert, and Guru. Sets taxonomy, style, and lifecycle standards; drafts, edits, and publishes articles; manages SME and compliance reviews; runs platform syncs and bot gap reviews; tracks content performance and readiness for product and policy launches; and builds the case to scale the team and transition execution to a dedicated Content Specialist.

Own monitoring, testing, and tuning of Inspira's AI virtual agent to improve resolution, deflection, and CSAT. Analyze conversation transcripts and performance data, run A/B and regression tests, adjust retrieval/configuration and intents, partner with Content and IT to fix knowledge gaps, maintain performance dashboards, lead root-cause analysis, and support go-lives for new bot capabilities.

Lead a regional account management organization for enterprise benefits clients, acting as executive sponsor and trusted advisor. Oversee and develop a team of Account Executives, drive retention, revenue growth, cross-sell, renewals, and QBRs, provide strategic consulting on CDH programs, and collaborate with product, implementation, and client success teams to deliver best-in-class service.

Support product and operations teams to design, document, and deliver scalable workflow solutions. Elicit and translate business, compliance, and operational requirements into testable user stories, process maps, and rule catalogs. Drive cross-functional alignment, operational readiness, and post-launch measurement to reduce risk and improve performance.

Lead a product squad for Retirement & Wealth to define vision, build investor-facing products, prioritize roadmaps, set OKRs, and drive measurable outcomes. Collaborate with stakeholders and Technology, enforce Agile best practices, ensure quality discovery and analytics-driven optimization, and coach Product Managers. Recruit, develop, and manage a high-performing product team while removing execution barriers.

Perform plan funding audits across pre-tax benefit platforms to identify discrepancies and missing funding. Review and document employer account activity, maintain trackers and audit records, escalate funding gaps, collaborate with Collections and managers to support recovery, create operating procedures, assist internal/external audit requests, and provide weekly reporting to leadership.

Build and validate predictive models, analyze large structured and unstructured datasets, generate business insights, present analytic results to stakeholders, and develop tools to advance analytics capabilities.

Senior Business Analyst in Digital Product Management who identifies business needs, analyzes data, and designs process and product improvements. Leads requirements gathering, creates epics/features/stories, develops functional specifications, conducts testing, and drives change management to streamline, automate, and standardize operations using data-driven insights.