Top Tech Jobs & Startup Jobs in Chicago, IL

Design, build, and productionize LLM-powered systems (adaptive content, tutors, evaluators) and AI pipelines (RAG, embeddings, fine-tuning). Prototype and optimize models across modalities, define AI safety/evaluation/observability practices, and collaborate with product and engineering to measure learner outcomes and iterate.

Lead and own AWS infrastructure for an LLM-powered enterprise coaching product. Design scalable IaC (Terraform, Ansible), CI/CD, autoscaling, networking and security (SIEM, EDR/XDR). Optimize costs, ensure high availability, collaborate with application and AI teams, and implement enterprise-grade security and compliance for Fortune 500 deployments.

Lead strategic finance engagements including financial and operating modeling, unit economics, cash management, and transaction support (M&A, equity/debt fundraising). Advise C-suite, implement process automation, oversee external providers, and deliver actionable recommendations to improve profitability, cash flow, and capital structure.

Produce AI-generated images, animations, and short videos from curriculum outlines for children ages 4–8. Build fast, repeatable pipelines, edit and assemble polished lesson videos, and partner with subject-matter experts to design educational activities that teach and engage.

Full-stack product engineer (backend-focused) who builds scalable NodeJS services, crafts React/TypeScript UIs, designs APIs, writes well-tested code, optimizes PostgreSQL queries and data pipelines, improves observability, and contributes to architecture and engineering practices for a fintech platform.

Lead finance transformation strategy and roadmap, oversee systems analysts and configuration of Yardi and BlackLine, drive transformation initiatives, manage change and KPIs, and ensure efficient monthly close processes while building a high-performing team.

Lead district sales and go-to-market expansion from initial states to nationwide adoption. Own full sales cycle—prospecting, demos, procurement, RFP responses, and closing—while building playbooks, managing CRM pipeline, shaping messaging, and representing Lilypad at conferences.

Represent Dorfman Milano in WY, CO, and NM by developing and managing retail accounts, driving territory sales through client visits, presentations, cold outreach, and trade shows; provide market feedback, maintain sales records, and collaborate with internal teams to ensure order fulfillment and customer satisfaction.

Lead technical sales engagements for networking and security solutions from discovery through close and operational handoff. Conduct customer discovery, design solutions, produce BOMs, proposals, RFP responses, demos, and technical presentations. Coordinate manufacturers, distributors, and internal teams to validate and implement scalable, secure solutions while maintaining CRM data and improving sales engineering processes.

Support the sales team by conducting cold calls, generating leads, assisting with sales strategies, handling administrative tasks, maintaining customer databases/CRM, and collaborating to meet sales targets while gaining hands-on experience.