Top Tech Jobs & Startup Jobs in Chicago, IL

Lead technical discovery with federal customers to define requirements and design secure, compliant cloud-native architectures. Build POCs/MVPs, produce architecture and deployment documentation, integrate third-party tools, guide implementations, and align sales, engineering, and product teams to deliver AI-driven knowledge management solutions for government environments.

Lead visual storytelling across brand, digital product, motion, and environmental experiences. Collaborate with multidisciplinary teams to translate research and strategy into high-fidelity deliverables, prototypes, and brand systems. Advocate for craft excellence, contribute to client-facing presentations, and iterate across exploratory and polished work to communicate user stories and strategic intent.

Develop, design, test and implement Curam customizations and interfaces. Build Curam rules, analyze and fix code defects, participate in design meetings, mentor developers, and collaborate with analysts and broader teams on large-scale enterprise n-tier web applications.

Manage post-sale customer lifecycle for AEC clients: lead onboarding, conduct health checks, resolve escalations, advocate for customers internally, and identify upsell and renewal opportunities.

Design, build, test, and maintain inbound/outbound Workday HCM and Finance integrations (Studio, Core Connectors, EIBs, Web Services/REST/SOAP). Lead technical lifecycle from requirements to deployment, create Workday reports and calculated fields, handle XML/XSLT, support security/networking for integrations, prepare documentation, and provide testing and post-production support.

Build, integrate, enhance, and support production-grade Generative AI and LLM applications. Develop AI agents, RAG capabilities, APIs, and enterprise integrations using JavaScript and TypeScript. Apply prompt engineering, model evaluation, monitoring, security, authentication, and responsible AI practices. Troubleshoot complex issues across application, integration, model, and platform layers while supporting CI/CD, testing, deployments, observability, and production operations.

Operate as a founder on client projects: own strategy and execution, present AI roadmaps, design and build AI systems (vision pipelines, document extraction, recommendation engines), ship solutions across varying stacks, communicate technical tradeoffs to non-technical stakeholders, and adapt quickly to different industries and tools.

Manage a portfolio of homeowner associations: attend board meetings, perform inspections, prepare meeting and financial packages, supervise vendors and staff, oversee ARB and AP processes, maintain records, and ensure compliance with management agreements and statutes.

Manage all aspects of mechanical projects in HVAC including estimating, scheduling, quality control, and liaising with clients and teams.

The Enterprise Solutions Executive drives strategic sales in the healthcare sector, managing new business and contract renewals while maintaining strong client relationships with C-suite executives.