Top Tech Jobs & Startup Jobs in Chicago, IL

Leads product design initiatives for Retirement & Wealth digital products from discovery through delivery. Conducts user research and usability testing, creates wireframes, flows, prototypes, and high-fidelity designs, and partners with Product, Engineering, Content, QA, and business stakeholders. Maintains scalable design systems, component libraries, and Storybook documentation while improving design-to-development workflows. Uses AI-assisted tools responsibly to accelerate ideation and execution, influences product direction, and advocates for consistent, user-centered experiences.

Develops and supports enterprise Salesforce solutions across the full software delivery lifecycle. Responsibilities include Apex and Lightning Web Components development, Salesforce configuration, integrations using REST and SOAP APIs, architecture contributions, automated deployments, code reviews, troubleshooting, documentation, and production support. The role collaborates with product, business, architecture, and engineering teams while promoting scalable, secure, maintainable solutions and continuous platform improvement.

Leads support center specialists by providing real-time guidance, resolving escalated accountholder issues, coaching and training team members, monitoring service and quality goals, and supporting performance reviews. The role also tests new products and software, updates policies and training materials, answers client inquiries, improves service efficiency, and manages special projects. The schedule is Monday through Friday, 11:30 a.m. to 8:00 p.m. CT, with seven weeks of training.

Provides advanced, multi-channel support to retirement and wealth accountholders through email, chat, voice, and text. Resolves escalated and complex account issues, explains processes and next steps, collaborates with internal departments, and supports account and investment inquiries. Mentors new specialists, assists with training and new tools, contributes to policies and procedures, participates in pilots and UAT, and serves as a subject matter expert.

Manage and grow institutional and retirement client relationships, coordinate onboarding with internal teams, identify upsell opportunities, represent Inspira at conferences and meetings, maintain client communications and reporting, and drive strategic plans with Sales Managers and partners to retain and expand business.

Provides technical and functional administration for the NICE CXone contact center platform. Responsibilities include configuring IVR workflows, users, campaigns, skills, and dashboards; integrating CXone with external systems; troubleshooting application and telecom issues; monitoring support queues; managing incidents and vendors; documenting processes; supporting testing and releases; analyzing interaction data; and training internal teams. The role also focuses on system reliability, compliance, security, performance, continuous improvement, and business-unit support.

Designs, administers, maintains, and supports hybrid cloud infrastructure across Azure, VMware, networks, operating systems, databases, and security appliances. Builds CI/CD pipelines and Infrastructure-as-Code deployments using Terraform or ARM templates, supports Kubernetes and AKS environments, configures Istio and Helm, and develops disaster recovery solutions. Troubleshoots infrastructure and SQL Server issues, improves reliability and cloud costs, maintains operational documentation, mentors engineers, supports tickets and critical incidents, and collaborates with development, client service, and business teams.

Supports the reliability and operational excellence of health benefits systems involving HSA administration, banking integrations, compliance, and money movement. Responsibilities include independently resolving escalations, monitoring dashboards and logs, triaging incidents, executing data corrections, maintaining runbooks, analyzing recurring support issues, and collaborating with engineering, product, treasury, and operations teams. The role also mentors teammates, contributes to postmortems, improves troubleshooting processes, and uses AI tools for prototyping and debugging.

Owns strategic enterprise sales for consumer-directed healthcare benefits, managing named accounts and complex 9+ month sales cycles. Responsibilities include stakeholder mapping, discovery, business-case development, technical demos, procurement and legal coordination, forecasting, and closing high-value B2B partnerships. The role requires executive communication, multi-threaded relationship building, technical integration fluency, and experience with HSA, HRA, FSA, benefits platforms, or related markets.

Partners with business leaders and HR centers of excellence to align human capital strategy with business goals. Provides coaching on employee relations, performance management, compensation, recruiting, talent development, succession planning, and organizational design. Investigates complex employee issues, mitigates legal and reputational risk, analyzes workforce trends, supports compensation reviews, and drives HR transformation and process improvements. Manages a program or specialty area while coaching and supporting team members.