Top Tech Jobs & Startup Jobs in Chicago, IL

Design and ship UX/UI for AI products, translating ambiguous requirements into polished, buildable interfaces. Own information architecture, interaction design, user flows, and high-fidelity Figma work while collaborating closely with engineers. Design AI-native interactions, data-dense products, progressive disclosure, and reusable design patterns across multiple client builds. Work quickly, make pragmatic scope decisions, and maintain quality in fast-moving, ambiguous environments.

Own end-to-end AI product development for enterprise clients, from requirements and rapid LLM prototyping through production deployment. Responsibilities include data modeling, ETL pipelines, integrations, evaluation, observability, security, reliability, cost management, and client communication. The role requires shipping real AI products, iterating based on usage, and independently managing ambiguous technical and product decisions.

Lead the design and implementation of a deterministic investment compliance platform for a major asset manager. Model investment restrictions, thresholds, exceptions, benchmarks, breaches, remediation, effective dates, versions, and provenance. Translate IMA and legal language into computable rules, create traceable semantic models, establish validation and scenario-testing practices, and guide implementation. Collaborate with legal, compliance, investment, engineering, and executive stakeholders while owning outcomes in a highly autonomous, client-facing role.

Own one or two client AI product engagements from kickoff through iteration. Translate ambiguous needs into requirements, backlogs, sprint plans, and evaluation criteria; manage timelines, scope, resources, and client communications; direct designers and engineers; ensure AI output quality; identify blockers; and develop repeatable AI-first delivery processes. The role requires client engagement experience, a track record of shipping AI products or features, strong communication, technical fluency, and independent ownership.

Partner with executives to understand business operations, identify and prioritize high-impact AI opportunities, define ROI, and create actionable roadmaps. Collaborate with engineers to scope solutions, inform architecture, maintain alignment with business outcomes, present recommendations to C-suite stakeholders, and manage handoffs to implementation.