Top Tech Jobs & Startup Jobs in Chicago, IL

Manage and grow relationships with Third-Party Administrators and JAA payors, develop business plans and strategies, oversee onboarding and implementation, resolve claims interoperability (837/835) issues, coordinate cross-functional teams, and use data and reporting to identify improvements and support partner performance.

Lead cross-functional strategic initiatives to translate strategy into scalable capabilities. Drive operating model design, governance, pilots, business cases, and executive communications while aligning stakeholders and enabling long-term adoption and delivery.

Senior hands-on AI engineer to design, build, and scale enterprise ML, generative AI, and agentic systems. Architect reusable services, APIs, microservices, and event-driven solutions; lead model selection, deployment, MLOps/LLMOps, observability, governance, and modernization; partner with stakeholders and mentor engineers.

Serve as liaison between Talent Acquisition and IT to design, configure, and optimize Workday Recruiting. Manage integrations with recruiting platforms, support release activities, troubleshoot production issues, partner with developers and vendors, and advise recruiters on system capabilities and process improvements.

Lead the Strategic Portfolio Office to translate strategy into measurable outcomes by establishing portfolio discipline, governance, and operating models. Enable AI, automation, and platform programs to move from POC to production, drive investment prioritization and value realization, build executive-grade reporting and decision materials, and develop enterprise execution capabilities across federated teams.

Lead enterprise M&A strategy and execution: source, evaluate, structure, negotiate, and close transactions. Drive post-close integration and value realization, build financial models, advise executives, improve M&A processes, and lead a high-performing corporate development team.

Lead enterprise Responsible AI strategy and governance, embedding controls, observability, and evidence generation across the AI lifecycle. Partner with AI engineering, data science, Legal, Risk, and Compliance to scale operating models, automate governance processes, strengthen model inventory/metadata, and support audit and regulatory readiness while advising senior leadership and driving cross-functional execution.

Lead enterprise AI and technology strategy, align AI/data/platform roadmaps with business objectives, partner with vendors (e.g., AWS), drive transformation, incubate innovation, influence architecture and investment decisions, and measure business value realization.

Lead enterprise governance intake, triage, prioritization, and execution for AI and technology initiatives. Build consistent intake/review processes, shift governance left into product lifecycles, partner with Responsible AI, Legal, Risk, Compliance, Product and Technology, identify automation and process improvements, reduce backlog, and prepare metrics and executive decision materials to improve governance speed and scalability.

Lead architecture and hands-on delivery of scalable, AI-enabled enterprise workflow products. Modernize legacy systems, build LLM/agentic solutions, define enterprise architecture and governance, drive adoption of AI-assisted development, mentor engineers, and partner across product, UX, security, and operations to deliver secure, resilient workflow experiences.