Top Tech Jobs & Startup Jobs in Chicago, IL

Lead execution of product initiatives for clinical decision support and pathways: manage delivery from kickoff to rollout, handle inbound requests via Jira, coordinate alpha/beta releases, conduct customer discovery, translate prototypes into implementation-ready specs, and support FDA documentation and cross-functional communication across engineering, clinical, sales, and customer success.

Build and ship core product surfaces and internal tooling for an AI-focused enterprise platform. Implement data pipelines, deploy with customers, collect feedback, and iterate quickly while working directly with the founder on architecture and execution.

Lead and develop a Strategic Account Management team to retain and grow largest SaaS customers. Drive account strategies, executive relationships, renewals, expansions, adoption, forecasting, and cross-functional collaboration to achieve retention (96%+), revenue targets, and increased platform adoption.

The AI Marketer/DevRel will enhance brand awareness through technical content, community engagement, and storytelling while fostering developer relations.

Evaluate AI outputs across pre-call, in-call and post-call advisor workflows in ORA. Classify failure modes, document patterns, iterate on prompts and knowledge-base entries, test fixes, and surface trends to drive improvements alongside Lead Analyst and engineering.

Provide hands-on legal engineering support to DACH customers using AI workflows: troubleshoot technical issues, create Help Center content, track adoption/ROI, and enable scalable AI adoption for legal teams.

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.