Top Tech Jobs & Startup Jobs in Chicago, IL

Configures and validates benefits administration systems according to requirements documentation. Reviews raw materials, completes system builds and self-QA, supports enrollment and implementation workflows, maintains process documentation, tracks productivity, prioritizes tasks, resolves escalated issues, and collaborates with internal teams. The role requires benefits administration configuration experience, strong data analysis and spreadsheet skills, attention to detail, requirements gathering, process-flow knowledge, and the ability to manage multiple priorities.

Supports the design of mobile benefits experiences through research, user flows, wireframes, prototypes, usability testing, visual design, and documentation. Collaborates with product, engineering, research, and content teams under guidance. The intern will explore iOS and Android conventions, contribute to design systems and accessibility, review implementations, and complete and present a focused mobile design project.

Own defined product features and workflows from discovery through launch and post-launch improvement. Create product artifacts, partner with engineering and design, incorporate customer feedback and analytics, manage roadmaps and backlogs, prepare launch plans, and monitor adoption and quality. The role requires cross-functional collaboration, benefits administration domain learning, responsible use of AI-enabled tools, and hands-on technical engagement with engineers, including troubleshooting and scripting for production support.

Supports the Product Innovation Team by modifying and optimizing SQL queries, visualizing data with BI tools, identifying insights, and analyzing enhancements. Participates in coding, testing, documentation, and discussions while providing customer service and managing multiple tasks. The internship requires at least 30 hours per week and emphasizes advanced Excel and visualization skills, plus familiarity with Python and SQL.

Processes complex employee benefits cases, including appeals, QMCSO orders, Medicare forms, POA requests, condolences, and claims. Verifies eligibility, updates records, manages coverage activation, prepares notices and reports, resolves documentation issues, and maintains compliance with HIPAA, IRS, and CMS regulations. Provides empathetic member support, handles escalations, protects sensitive information, supports process improvements, and collaborates with internal teams and external partners.

Tests web, API, and batch applications through manual and automated test cases. Documents defects and test results, monitors bug-tracking systems, collaborates with engineers and business analysts, and applies quality assurance methodologies throughout the SDLC. The role requires strong problem-solving, creative thinking, and the ability to assess potential impacts and propose solutions that improve client satisfaction.

Tests web applications, Web APIs, and batch applications through manual and occasional automated testing. Creates and executes test cases, documents results and defects, monitors bug tracking systems, and collaborates with engineers, business analysts, and stakeholders. Requires knowledge of quality assurance methodologies, SDLC, and Gherkin test formats, with a focus on identifying software issues and proposing improvements.

Design, develop, maintain, and review UI and API test automation using Cucumber and related tools. Document test cases, manage test data, analyze failed and long-running tests, perform manual testing, and integrate automation with CI/CD environments. Collaborate with software engineers, product teams, and Scrum teammates to improve test coverage, troubleshoot defects, clarify requirements, and maintain quality practices. The role also includes estimating work, participating in test planning, and mentoring team members.

Develops, tests, deploys, and supports major software features and services. The role translates product requirements into maintainable technical solutions, makes design and performance trade-offs, performs root-cause analysis, conducts code reviews, improves development and deployment practices, and mentors newer engineers. The position requires collaboration across engineering and product teams and includes working with Java, SQL, XML, web technologies, JavaScript, and Oracle databases.

Drive enterprise sales for Businessolver’s benefits SaaS platform, targeting organizations with 12,000 or more employee lives. Responsibilities include prospecting, channel partner development with brokers and advisors, platform demonstrations, consultative selling, pipeline management, presentations, opportunity tracking, reporting, and guiding deals through implementation and close. The role requires strong relationship-building and sales discovery skills, experience selling technology to large organizations, and travel up to 50%.