Top Tech Jobs & Startup Jobs in Chicago, IL

Lead technology strategy and delivery for healthcare products, managing engineering teams and Scrum Masters. Drive cloud-native application development, operational excellence, observability, incident prevention, and AI-first automation. Own project planning, budgets, staffing, documentation, code reviews, and stakeholder alignment from design through deployment and maintenance.

Owns Medicaid product vision and roadmap for an Agile team: defines and prioritizes backlog, writes functional stories, coordinates SIT/UAT, showcases demos, supports releases, and liaises with stakeholders to deliver product value on schedule.

Lead the design, development, and deployment of scalable digital platforms and AI-enabled solutions. Mentor engineers and collaborate with cross-functional teams on technical architecture and engineering vision.

Lead discovery, prototyping, and delivery of AI/GenAI products. Define PRDs, build prototypes, scope requirements, run evaluations, partner with engineering/data/design, and shepherd solutions through enterprise AI governance to production.

Lead development of AI products from discovery through production: define strategy and roadmap, prototype with agentic tools, translate business problems into scoped AI use cases, own requirements and delivery, design evaluation and quality metrics, support solution architecture, lead cross-functional teams, navigate enterprise AI governance, and mentor product managers.

Support Humana's Corporate Strategy team by conducting market and competitive research, building quantitative and financial models, synthesizing findings into executive-level recommendations and presentations, and converting strategy into prioritized roadmaps and business cases while collaborating cross-functionally.

Lead and deliver high-priority strategic projects across the enterprise: analyze growth opportunities, build business cases, develop market and competitive strategies, translate recommendations into implementation plans, mentor analysts, and collaborate with senior leaders including the CEO and Executive Leadership Team.

Support enterprise strategic initiatives by conducting quantitative and qualitative analyses (financial modeling, market research, competitive assessments), developing executive-level presentations, evaluating growth and M&A/partnership opportunities, advising business leaders, and collaborating across functions to set long-term strategy and operational improvements.

Design and develop enterprise application architectures aligned with enterprise standards. Lead technical planning, create architecture artifacts, evaluate integrations, define specifications, and guide teams on APIs, microservices, containers, cloud, event-driven and secure design practices. Influence strategy and make technical decisions for complex projects.

Lead design and delivery of scalable, secure AI/GenAI applications: gather requirements, architect LLM-driven solutions (RAG, vector DBs, prompt engineering), build resilient microservices and pipelines, ensure Responsible AI and healthcare compliance, coordinate testing and production readiness, and lead cross-functional teams and vendors to achieve business value.