Top Tech Jobs & Startup Jobs in Chicago, IL

Lead the architecture, development, and operation of enterprise-grade full-stack software for clinician-facing and performance-management experiences. Design distributed systems, drive technical initiatives, improve scalability and maintainability, adopt modern technologies, deliver iterative releases, and collaborate across organizations. Mentor engineers and establish strong engineering practices. The role requires polyglot programming, cloud platforms, modern front-end development, SQL, distributed systems, and production operations experience.

Leads the Finance Technology AI Enablement engineering team, setting technical strategy and delivering AI, ML, and GenAI solutions. Responsibilities include managing and mentoring engineers, translating business needs into technical roadmaps, overseeing concurrent initiatives, establishing scalable architecture and DevOps practices, and ensuring governance, security, privacy, and compliance. The role also advises stakeholders on AI adoption, enables low-code and full-stack solutions, and reports program value and risks to senior leadership.

Manage engineering operations across planning, governance, budgets, workforce coordination, vendor and SaaS asset management, security reviews, compliance, disaster recovery, and executive reporting. Partner with engineering, product, delivery, finance, procurement, security, and vendors to track priorities, resources, risks, costs, and operational performance. Support onboarding, leadership meetings, communications, learning programs, audits, and process improvements across a matrixed technology organization.

Designs, develops, deploys, and supports complex integrations between Workday and internal or external systems. Builds Workday Extend and Orchestrate applications, configures Studio integrations and connectors, manages APIs, data migration, release updates, documentation, production support, and incident resolution. Partners with technical and business stakeholders, coordinates vendors, contributes to Agile projects, and mentors team members while ensuring scalable, secure, and maintainable integration solutions.

Leads payer deal intelligence, financial modeling, market analysis, and negotiation decision support for pharmacy reimbursement agreements. Builds multi-year scenarios, sensitivity analyses, and pre-negotiation packages; recommends deal positions and walk-away points to senior leaders. Manages concurrent analytical deliverables, translates quantitative findings into executive recommendations, and supports cross-functional finance and payer strategy forums.

Leads the Excalibur team’s enterprise data science and AI strategy while personally designing, developing, deploying, and monitoring machine learning, predictive analytics, and generative AI solutions. Builds Databricks data pipelines and products, self-service analytics, and conversational data experiences. Establishes engineering, governance, testing, and MLOps standards; owns technical roadmaps and architecture decisions; partners with stakeholders; and mentors data scientists, engineers, and analysts.

Lead AI adoption and enablement for Pharmacy Services Finance by delivering role-based training, workshops, coaching, communications, prompt libraries, and practitioner communities. Measure adoption and learning effectiveness, identify literacy gaps, support responsible AI use, and convert coaching insights into reusable resources. The role focuses on Microsoft Copilot and Claude tools, stakeholder collaboration, behavior change, and hands-on support rather than AI engineering, governance ownership, or product management.

Design, build, and maintain scalable automated test frameworks for web and mobile using Playwright, Selenium, and Cypress. Develop API and end-to-end tests, integrate tests into CI/CD pipelines, lead defect triage and root-cause analysis, ensure healthcare compliance (HIPAA/Medicare), and leverage agentic AI tools to accelerate test authoring and maintenance.

Leads enterprise capital planning, month-end close, reporting, forecasting, operating plan support, investment analysis, and portfolio performance monitoring. The role consolidates segment submissions, evaluates financial assumptions, prepares executive insights, maintains reporting governance, and serves as a subject matter expert for capital planning systems. It partners with Finance, Accounting, Treasury, Technology, and capital stakeholders while coaching analysts and improving reporting processes.

Supports cross-business strategy and operations for CVS Health’s Diversified Commercial Solutions organization. Responsibilities include managing financial and business-priority reporting cadences, leading cross-functional strategic initiatives, improving collaboration across a complex matrixed organization, and developing content for executive meetings and external events. The role partners with senior leadership to drive execution, transparency, growth, and operational accountability.