Top Tech Jobs & Startup Jobs in Chicago, IL

Own the company’s AI-powered quality and release infrastructure as its first dedicated hire. Build agent-run test harnesses, LLM graders, regression coverage, release gates, fresh-install and upgrade verification, and natural-language UAT. Manage CI health, artifact publication, deployment pipelines, credentials, certificates, and staging environments. Write production Python code, convert escaped bugs into regression tests, and provide trusted release-readiness evidence through dashboards, runbooks, retrospectives, and operating policies.

Own the full sales cycle for an AI-powered corporate compliance platform, from self-sourced prospecting and discovery through demonstrations, negotiation, and close. Sell to General Counsel, CFOs, Corporate Secretaries, and compliance leaders while maintaining pipeline, activity, conversion, and quota metrics. Partner with BDRs as inbound demand grows, continue self-sourcing approximately one-third of pipeline, and travel for prospect meetings and industry events.

Conduct original research on reliable agentic AI, developing methods for simulation, evaluation, optimization, regression control, and continuous learning. Analyze agent failures, traces, and human feedback; create experiments and prototypes; and translate research into production-facing systems. Collaborate with product and engineering teams, contribute to technical strategy, and provide rigorous experimental evidence. The role requires strong research depth, publication or open-source contributions, hands-on Python development, and expertise in LLM agents or agentic systems.

Own full-funnel growth and performance marketing for an enterprise B2B SaaS company. Responsibilities include managing paid media and ABM programs, building attribution and reporting infrastructure, optimizing campaigns, managing a seven-figure budget, maintaining the martech stack, and partnering with sales to drive pipeline, revenue, CAC, ROAS, and payback outcomes.

Own backend-heavy product and platform engineering from design through production. Build and scale distributed systems supporting large-scale mortgage transactions, design reliable infrastructure for regulated workflows, contribute to architecture and engineering standards, and collaborate with product, infrastructure, and platform teams. Use AI coding tools while maintaining rigorous human review and correctness.

Build end-to-end frontend and backend features for a voice AI trust platform while working directly with enterprise customers. Responsibilities include customer discovery, debugging, proofs of concept, product decisions, reusable platform development, and post-sales technical support. The role requires TypeScript and Python proficiency, AI coding tool fluency, strong product judgment, clear communication, and approximately 10%–20% travel.

Lead sales strategy and execution for an early-stage vertical SaaS company. Personally run demos and close complex new-logo deals, build sales processes and forecasting from scratch, recruit and develop sales representatives, and partner with Marketing and customer-facing teams. This remote player-coach role reports to the CEO and may grow into broader VP or CRO leadership.