Top Tech Jobs & Startup Jobs in Chicago, IL

Own the company’s legal function, including commercial contracts, corporate governance, equity financings, litigation finance, legal-services regulation, privacy compliance, outside counsel management, and company risk. Advise on employment, intellectual property, marketing, AI governance, threatened litigation, and defense correspondence. Requires substantial transactional and corporate experience, litigation familiarity, and a mix of top-tier law firm and in-house experience.

Lead development of Chariot’s claims processing pipeline and CRM systems, transforming manual scripts into reliable, observable production infrastructure. Build claimant and law-firm workflows, fraud detection and verification stages, dashboards, integrations, internal tooling, and AI agent harnesses. Own product decisions, recruit and develop engineers, and establish pipeline reliability. The role requires staff-level software ownership, early-stage startup experience, and proficiency with Go and AWS.

Engineering Lead responsible for Chariot Claims’ consumer acquisition and claim-filing funnel, claimant communications, evidence and signature collection, dispute scheduling, and payment disbursement systems. The role owns technical direction, rapid experimentation, platform foundations, AI-native tooling, and team hiring and development. Candidates should have staff-level production software experience, strong product judgment, early-stage startup experience, and familiarity with payments or money-movement systems.

Lead the engineering team building Chariot’s AI claims platform, including agent systems for case origination and claims matching, human-in-the-loop review, evaluation infrastructure, and scalable AI performance. The role owns product decisions, internal tooling, cost efficiency, and production reliability while recruiting and developing full-stack and ML engineers. Experience with production software, end-to-end product ownership, early-stage startups, and modern LLM systems is valued.

Lead Chariot’s consumer platform engineering function, building community, education, case discovery, referral, trust and safety, and growth-loop products. Own product decisions and end-to-end delivery, contribute to shared AI-native platform tooling, recruit and develop engineers, and establish production systems using TypeScript, React, Go, and AWS.